It’s not the first mistake, it’s the second,” world champion sailor Bora Gulari once said while I was coaching him in the Nacra 17 for the US Sailing team. When asked if it was OK to quote him, he said, “In fairness, I got that from Terry Hutchinson.” Regardless of the origin, I like its message—that the unexpected is inescapable, and that it’s how we manage problems that matters. That doesn’t mean being complacent, however. It means finding solutions.

When I’m sailing, I make ­mental notes of any adversities such as “spinnaker takedown late.” Then, once onshore, I add details into the Adversity Spreadsheet that I keep. It’s an incredibly useful tool to keep those second mistakes from happening again. I recently added an Impact column to the spreadsheet, which is a measure of how many boats were lost due to a noted adversity. This is easy to estimate sometimes, such as our flubbed takedown cost us two boats, so the impact is simply “2.” But it’s harder to estimate the impact of a bad start. Did it cost me 15 boats at the moment, or five? All I can do is make my best guess.

The Impact column also helps me identify my repeat offenders, understand which ones cost me most, and motivates me to work on improving. It’s eye-opening that, for any given regatta, even in winning, I might have an impact of 30 or more. In losing, I might see just a few things I could have done better that would have made all the difference.

This Impact column has led me to pondering the risk ­versus reward trade-offs of an OCS. For example, I recently sailed a regatta where I pushed the line and was OCS in one of the 10 races. But the other nine starts were excellent. It’s hard to measure, but maybe my finishes would have been five places worse per race if I’d held back. Over nine races, that’s 36 points. But the OCS cost me 60 points. Without a discard, ­pushing the line risking an OCS is a major error, but if there were a discard, I get to shed those 60 points, so risking the line is the right move.

The whole point of ­gathering all of this information into the spreadsheet is to come up with solutions. For our poor spinnaker takedown, my teammates and I concluded that there were two solutions. The first is to start the process a little earlier when we are not fighting for mark room. But when we don’t have that luxury, we came up with a process change: When we need to carry the spinnaker late, we need to put the board down and jib up very early, then strip the pole and free-fly the spinnaker. The Solutions cell in the spreadsheet can be simple and to the point, or long and in depth.

Boathandling adversity is definable and mostly in our control. Practice is usually the solution, but in the long run, I think that the best way to reduce it is to empower each team member to succeed and equally empower them to be human and, with that, make mistakes. When I see someone on another boat lay blame and even yell at their team member, I cringe. I expect an occasional boathandling error from my teammates, and they expect the same from me. In the moment, the right response is to work together to recover. Then, after the race, the spreadsheet is a low-conflict way of defining problems.

Boat-on-boat tactical adversity is often our mistake. If I am on port tack and feel strongly about wanting to get right, for example, a mistake would be to lee-bow a starboard tacker instead of taking the big duck. Most tactical errors can be solved by the tactician clearly planning and communicating. A good comms example would be: “We are going right, so if anyone comes, then we are ducking.” It reinforces planning for specific moves with an if/then.

Strategy is an interesting study in adversity mitigation. We can put solid thought into our race strategy, but in the end, Mother Nature does whatever she wants. Suppose I identify the adversity in my spreadsheet as: “I went left as local knowledge dictated, but instead a persistent righty won.”

If, in looking back, I can see no way to have predicted the right shift, I can’t count that as an error. However, the error might be that I did not mitigate the damage. The root cause would be: “I did not see the righty soon enough.” The solution could be: “We need a team member assigned to regularly to check the opposite side of the course for signs of change.”

Boatspeed adversity is the most frustrating because the root cause is often hard to identify and elusive to solve. But it is always in our control. 

For adverse tactical situations over which we have little control, we switch our focus to mitigation. Suppose we identify adversity as “we were tacked on.” We might call it an error because “we tacked into too good a lane and it was inevitable we were getting tacked on.” The solution should be: “We should have tacked in a compromised lane, that way the odds of ­getting directly tacked on would be low.”

One easily identifiable adversity is a protest situation. Many fouls can be avoided with clear communication with competitors. Suppose the error was: “We thought it was obvious that we were clear ahead at the zone, yet someone jammed in anyway.” The root cause is: “We did not communicate that they had no room.” The solution is: “We should always start the overlap conversation 10 ­boatlengths out. Doing so establishes the overlap status in case of a protest situation, but more importantly, it leaves enough time for both boats to think things through and be mentally prepared to round in the proper order.”

Boatspeed adversity is the most frustrating because the root cause is often hard to identify and elusive to solve. But it is always in our control, and as such, is listed as a mistake in our spreadsheet. If the problem is: “We are slow in medium wind and chop,” and the root cause we might have to write is: “We have no idea why.” In this case, the solution is: “We need to ask some of our friends who are doing better in this condition, come up with a list of things to try, and then find medium wind and chop to train in with a tuning partner.” There is no simple solution to boatspeed woes, but to do well, we must be fast, so we must never stop working on speed.

An ongoing boatwork list, along with regular inspections and replacements, takes care of most mechanical adversity. But mitigation comes into play too. For example, born from things going wrong, I have added redundancy to some systems. For example, my outhaul broke once, and it’s ­impractical to inspect it often because it’s inside the boom, so I have added a safety line. I’ve busted my spin pole more than once, so now I carry a spare. While coaching, whenever my athlete asks, “Do you think I should replace my—” I interrupt with a “Yes!” before they can finish. It does not matter what they were about to identify, if they question whether it should be fixed or replaced, it should be. If ­nothing else, for peace of mind.

Managing adversity is a deeply personal mental game. For me, when something goes wrong, I take a deep breath, hold, then exhale. It probably takes only about 5 seconds for that full cycle, the amount of time my brain needs to move on. And with my breath held, I can’t possibly do something in the heat of the moment that I will regret.

I once coached an ­emotional team of three sailors, and we used the word “helicopter” to get the team back in focus. Anyone on the team could say it, and the agreement was that the others would each visualize being dropped into their boat from a helicopter, with no knowledge of how they got into their current position. The message was: “No blame, no bad history, just focus and hard work from where we are.”

Even in winning major events, I have never raced without plenty of adversity. Some clear mistakes, some completely out of my control, and plenty somewhere in between. I have learned to expect them, and with that, I am free to move on to managing whatever the problem might be. In the moment and with a clear head, I want to quickly come up with the best solution. Postrace, I want to identify the root cause and hopefully agree with my team on a solution. Even if I can’t identify the root cause, the solution will be to study it to find the root cause. Those that are squarely in my control, such as ­boathandling, I want to do everything I can to eliminate. Others, such as picking a side, are less in my control and I am only playing odds. For these, I work on mitigating their damage. But most importantly, when the inevitable problem does come our way, I want to empower my team to do the best they can to mitigate the damages and move on, ­avoiding that second mistake.

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One of the coolest uses of a centerboard I’ve ever seen was at the Smythe Laser Championship qualifier—a junior sailing regatta. The two best sailors were fighting for a chance to go to the finals as they approached the leeward mark with the trailing boat barely overlapped. In an amazing move, John Torgerson, who was slightly ahead of the competition, pulled his daggerboard up all the way, and pushed his tiller toward the competitor to start sliding sideways, breaking the overlap. He literally slid into the zone like a race car drifting around a corner and started hailing, “No room!” He then slammed the board back down into the trunk and jibed to round the mark ahead. There was a protest, but he prevailed in the end and off to the Smythe finals he went. So cool.

For many dinghy sailors, the centerboard is hardly a consideration. It tends to be out of sight and out of mind, and either up or down or somewhere in between, but rarely dynamically adjusted. As a high school sailing coach, I can see that most sailors focus on other skills first before thinking about the importance of the centerboard, but this important underwater appendage can make a world of difference in your performance and speed, so let’s discuss in the simplest terms how it’s best used.

The first rule of thumb is that you want your centerboard, daggerboard or leeboard all the way down while sailing upwind to create more lift and side force, and to give you more power while reducing leeway. Downwind we prefer the board as high as possible to reduce drag while keeping the boat tracking, especially if we’re not sailing dead downwind. And let’s not forget stability—no sense in capsizing for a small gain in boatspeed. 

In most boats, this means putting the centerboard all the way down upwind while sailing in light to medium winds. On some boats and in certain windspeeds, it can be faster to pull the board a few inches, but we’ll get to that later. As a point of making sure the centerboard is fully down and then some, I’ve noticed top FJ and 420 sailors experiment with the type of blocks used on top of the board to allow it to go down just a little bit more than the competition. This deeper board gives them more power and less leeway upwind, which is a performance gain. 

Downwind, if running very deep, let’s say close to dead-downwind, we don’t need the board dragging through the water, so we can pull it all the way up. However, if the boat starts rocking excessively and is hard to control, we can drop the board down until the boat becomes stable—think of this as your “roll control.”

Top high school and college sailing crews are very active with the centerboard downwind, dropping it down a few inches in puffs to prevent the boat from overheeling, and pulling it up in lulls when it is less needed. Playing the board can be very fast.

If you are reaching, the basic rule of thumb is to pull the board up until you notice the boat starting to slide sideways, then put it down a touch so that you are tracking straight. By doing so, you’re reducing drag as much as you can and using only the amount of board necessary to track and go forward.

When sailing downwind with the board up to some degree, it’s also effective to put it down for a maneuver, which gives you stability and helps you power forward out of roll tacks and roll jibes when you’re generating a lot of side force. As a bonus, it also clears it out of the way for the forward crew in doublehanded and triplehanded boats. 

For more high-level thoughts on centerboards, I reached out to my friend Will Ryan, a fantastic Olympic International 470 gold medalist. After dominating the class for many years, he’s got a solid handle on how and when to play the centerboard. As a general rule, he says, having the centerboard to its maximum down position is useful when sailing upwind or in light air. Having the centerboard at its maximum down (or vertical down such as in an International 470 or 505) helps the foil create its maximum side force, which helps generate power in the boat and to create lift. That’s a good combo. This setup is also fast when you’re overpowered but trying to sail a “high mode.”

In smaller boats especially, Ryan adds, pulling the board up a few inches in breeze is fast: “The centerboard acts as a power control. Water has more drag resistance than air, so the benefits of reducing hydrodynamic drag can outweigh the benefits of reducing aero drag (smaller sails) because often the bigger sails can still be useful on the downwind legs.”

For many dinghy sailors, the centerboard is hardly a consideration, but this important underwater appendage can make a world of difference in your performance and speed.

Ryan also reminds us that raising the centerboard is a good way to optimize the balance of the boat when overpowered: “Changing the centerboard’s side force can make the boat more responsive  to gusts and easier to handle in waves, while also making the boat easier to steer, which generally makes the boat easier to control. Upwind, more side force might be required from the centerboard to help with the boat performance (because the lift from a centerboard is related to the speed it is moving through the water). Conversely, more centerboard up may be used downwind when the boat is traveling faster (a smaller centerboard area still giving the same amount of required lift or stability with the boat traveling at a higher speed) or when the course of the boat does not require as much side force (i.e., downwind); even less centerboard can be used in the water because reducing wetted surface area might be even more beneficial.”

In lighter airs, he says, some boats such as 470s and 505s can rake the centerboard forward—even forward of 90 degrees. “Raking the board forward can help to provide a greater side force, giving the boat more power. The board shape can create more lift, and this can also help to optimize the maneuverability of the boat because it makes the distance greater between the rudder and the centerboard. On boats such as these, where sail shapes have a number of available controls, and mast rakes or mast step adjustments are also allowed, the rake change of the foil can also help to balance the boat for better upwind performance.”

Next-Level Board Play

What we’ve covered so far are mainly straight-line considerations, but let’s take it back to Torgerson’s slick slide into the zone at the Smythe. If your ­centerboard adjustment is easy to play, consider how you might use it like Torgerson did so masterfully. Someone once told me about what he called the “­prestart slide.” If he got to the line a fraction too early, was exposed, and had room to leeward to rumble, he would turn to a reach, pull up the board quickly, and laterally slide the boat one width to leeward. When it was time to turn up, all he had to do was drop the board, let it bite, turn, and trim.

In the prestart, Ryan says, having maximum centerboard down provides the aforementioned side force (or grip) to help hold a boat in position, and minimize leeway. This can be particularly helpful when the boat is sailing at slower speeds. Keep in mind, however, that you’re not overpowered when you trim in and go. Also, raising the centerboard a little might help the boat to bear away and accelerate.

One additional tip Ryan shares is that for small boats that might be prone to getting caught in irons, or ones that don’t have a jib, raising the centerboard briefly can help get a boat to rotate the bow away from the wind. This is not a practical maneuver on all boats, but having some centerboard angled aft or raised up a bit can also help on the exits from tacks.

Here’s my final thought on the centerboard when in close quarters, and this applies ­especially in windward/­leeward luffing scenarios. If you’re the weather boat, remember to drop that board before the attack. And if you’re keen to try Torgerson’s move, remember to drop it before the turn—unless, of course, you like leaving the barn door open.

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Much has been written in ­textbooks and articles about how to win sailboat races once you cross the starting line, especially when it comes to tactics, speed and boathandling. And while it is true that races are won and lost between the start and finish lines, it’s also true that the outcome of any race or regatta can be affected by what happens well before the start. Here we’re talking about building an overall plan for the day before we even suit up to go racing.

Our first order of business is to align with our teammates on our goals for the regatta well in advance, which will ­eliminate any stress that creeps in when or if your expectations and actual performance don’t match up. If your team is intent on bringing home a trophy, it usually makes for an awkward dynamic on board when you choose to win the regatta party instead. Step one is to set performance-related goals, like “finish in the top 10.” Our performance or results-based goal will be determined by factors that are outside our control, so the second type of goal is even more important: ­process-oriented objectives that are completely in your control. For example, if we expect a shifty and puffy venue, we will set a goal to “look up the course to identify the first puff at one minute before every start.” On the other hand, if we anticipate steady wind, making boatspeed the critical element, we would set a goal to line up with multiple competitors before the start and check our control-line marks for the first sprint off the starting line. Putting these goals in writing will give us a framework for debriefing after each day of racing. It also allows us to better divide and conquer the pre-regatta homework.

Speaking of homework, let’s talk about hitting the books. A little research can go a long way to minimize surprises during the regatta. Start by printing or taking a screenshot of the racecourse areas and annotate the common breeze directions. Familiarize yourself with the body of water and surrounding land features so you can put the forecasts and local knowledge into a geographical context. Identify which weather-­forecasting app is most useful for the region, and make sure your subscription is up to date. Ask local racers about which forecasting model they find reliable. If you don’t know anyone, check out the validation feature on the PredictWind app. Local airports and fishing, surfing, and NOAA websites are excellent sources because these entities catalog a ton of historical data. The goal is to better understand the regional weather systems during the regatta window, the direction and strength of the typical sea breeze, and the ­influence of currents or tides. At a minimum, you will make better-informed choices when deciding which wetsuits or spray gear to bring. 

Once you have a general idea about the venue’s ­predominant wind characteristics, brush up on wind-related strategy basics. My favorite textbook to reread is Wind Strategy by David Houghton, and you can also find great web-based resources from sites like Sea Tactics by Chelsea Freas. If we are sailing in a bay like Palma de Mallorca, the typical sea breeze creates a racecourse with a left-hand shoreline looking upwind. This tells us we can expect convergence on the left side of the racecourse, so we’ll likely have some drag races from the starting line to the shore and need to be set up for it.

Practice Winning Moves

Visualizing the winning path and rehearsing likely tactical scenarios will build confidence during your pre-regatta training. In the Palma example with a left-dominant racecourse, our pre-regatta training will focus on strong boat-on-boat positioning off the starting line to control our lane to the left corner. Drills that replicate the left-corner-exit scenarios provide a chance to practice communication during critical moments, such as: Are we going to be the first or last boat to tack out of this corner? Can anyone tack on us?

On a shifty, high-tempo ­racecourse, being able to tack or jibe on a moment’s notice will be important, so maneuver readiness should be a focus of our boathandling training. All of our venue homework should give us a sense of what style of racing we can expect and the best way to establish good ­habits and confidence. 

Study Your Competitors

It’s beneficial to skim through class-results archives to get a sense of which teams dominate in certain conditions. For example, we can avoid starting next to the fleet’s light-air experts. Look for trends, like whether a fleet is generally conservative or aggressive on the starting line. It also helps to identify our fleet’s starting-line repeat ­offenders so that we don’t get tricked into being pushed over by a team who has a history of OCS penalties. This is especially important in fleets who cannot use GPS instruments. It’s important to know who tends to misjudge the starting line. There is one caveat, however. A venue with strong current can introduce unique starting challenges. For example, we can take Charleston Race Week scores with a grain of salt.

It also helps to identify our fleet’s starting-line repeat offenders so that we don’t get tricked into being pushed over by a team who has a history of OCS penalties. 

Also, we examine the score lines of teams with the same performance goal we set for ourselves at recent, ­similar-size events. We like to set a daily-total-points goal for ourselves each day before racing. Focusing on our average score line should help us avoid desperate and risky decision-making.

Race-Day Preparation 

When looking at the forecast on the morning of the regatta, make mental notes of the most important things, and don’t try to memorize it all. Knowing the minimum and maximum of the velocity range and expected trend will help us make informed choices about our rig and sail settings throughout the day. The most important piece of information we want to pull from the forecast is what type of breeze we will race in because that will dictate our priorities on the racecourse that day.

Try to identify whether you’re going to sail in a sea breeze by looking for the key ingredients for a thermal: a land and water temperature difference greater than 5 degrees and a forecast direction more or less blowing perpendicular to the shoreline. Expect three major trends when racing in a true sea breeze in the Northern Hemisphere. First, as the breeze builds with heating over land, it will likely veer (shift to the right). Once the breeze is established, watch for small, rhythmic oscillations. Then, as the breeze fades in the evening, look for the direction of the wind to get pulled toward the angle of the gradient wind aloft.

If we don’t have the key ­components of the sea breeze, the forecast can still help us understand the likelihood of predictability. For example, if our forecast calls for an offshore wind throughout the day with a wide range of direction and velocity, we get ready to follow our instincts and sail what we see at the moment. If we see that we’re going to sail in a gradient breeze, our challenge on the water will be to determine a pattern to the oscillations. Look closely at the predicted directions throughout the day to see any hints of a persistent shift. We treat the first few hours of the day as if we are detectives trying to determine the accuracy of the forecast. Look at the wind strength, direction and clouds to see if things are aligning. Forecasts give us clues about possible patterns, but most of the time, it’s only that: clues. We are trying to find indicators of the expected change, such as a temperature drop and darker clouds that can be a red flag for a storm system nearing. Even if we don’t know exactly what the new system will bring, telling ourselves to be heads-up for a change here can give us an edge over our competitors. There will be days, however, when we have to ignore the forecast and sail what we see. 

On the Racecourse

The hour before the race is our last chance to gather the final and critical pieces of information: starting-line and racecourse geometry. Before each race, check the race committee board to find the bearing to the windward mark, and identify the compass heading numbers that are “neutral to the course.” Compare the compass bearing of the starting line to the compass bearing of the head-to-wind numbers to determine the bias of the starting line. These data points won’t usually dictate our strategy for the race, but occasionally, we find an opportunity to gain an ­advantage off the starting line. 

Now comes the most important moment of our pre-race preparation: determining what we need to prioritize. If we’re sailing in light air or in a steady breeze, we need a comfortable upwind lane off the starting line, so we will need to set up in a low-density area, home in on our distance to the line, and determine if we want a two- to four-tack beat. If we see puffy, shifty craziness upwind, we choose our starting position as late as possible to keep our options open, remaining ready for anything and reminding ­ourselves to stay flexible. 

In an ideal world, we can accurately predict the priorities of the racecourse and execute flawlessly. The easy answers of racing to a geographical feature are convenient but actually rare. Usually, only hindsight makes the winning strategy perfectly clear. The most important skill, which takes humility and confidence, is admitting when we don’t know what will happen on the racecourse. There should be no shame in the no-plan plan. We must come to terms with unknown variables in order to be open-minded enough to learn as the racing unfolds. Ultimately, developing a solid racing strategy requires skills in filtering information, remaining adaptable, and learning as you go throughout a race, a day, and a regatta. Now go get ready.

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When boatspeed comes up in a debrief with your team, ask yourself: Did we put ourselves in a position to be fast on the racecourse? If the answer is no, do not waste your time on the topic. A few things have to be good enough before you leave the dock. Will your sails and hull allow you to be competitive? Is your team close to the overall target weight? The best sailors can make slow boats and old sails go fast, but for most of us mere mortals, it’s much harder with bad gear.

There are a few more caveats on the racecourse. If your upwind lane is compromised, you cannot evaluate your boatspeed. Even the fastest sailors in the fleet cannot defy the physics of being on another boat’s windward hip. Instead, they are usually better at tacking away before too much distance is lost. Also, a boat can be optimally set up, but improperly trimmed sheets or an erratic hand on the tiller will make it perform like it’s towing a clump of weeds. 

All this is to say it’s critical that you make sure your team is doing the big things well—getting off the starting line, choosing smart moments to tack, and executing reasonable trimming and driving technique—before blaming boatspeed. 

Aside from boat-specific equipment optimization, any speed-­related problem-solving on board requires solid communication between the skippers and trimmers. The words we use matter; onboard communication related to speed should be concise, direct and actionable. On board the 49erFX, for example, my teammate Stephanie Roble will often tell me the “boat won’t release” when a puff hits. When I hear this, I know we need more twist in the mainsail. Here, Steph is giving me feedback that I can act on and address. When using adjectives to describe the boat’s performance, make sure you’re all on the same page about the meaning of terms such as “sticky,” “wobbly” or “narrow groove.” Ultimately, if the boat is set up properly, speed-related communication should be mellow. A quiet boat is a fast boat.  

The tiller gives us some of the most valuable onboard feedback about the setup of the mainsail and jib in relation to each other. When sailing upwind with the sheets fully trimmed and the crew hiking appropriately, have the skipper release their grip on the tiller and take note of what happens to the bow. If there is a strong reaction to leeward or windward, you might have an imbalance in the setup of the mainsail and jib. If the bow gets pulled too leeward, away from the wind, it can indicate that your jib is too powerful or the mainsail could take more leech load. The opposite might be true if the boat wants to naturally round up when the skipper eases their grip on the tiller. If so, your mainsail might be too powerful. On most dinghies, the helm will not ever be totally neutral, but an extreme windward or leeward helm tug indicates you can find a better balance between the mainsail and jib. To keep things really simple, sometimes I ask Steph, “Are you pushing or pulling the helm?” 

When you sail upwind to check settings, ensure the skipper and trimmer are aligned on wind strength and where it leaves you in the power curve. Are you searching for power, trying to use the max power available, or needing to depower your setup? The answer usually varies across the day’s wind conditions, such as: “Overpowered in the puffs, but OK on average.” This analysis should lead you to the next decision about whether you set up for the puffs or lulls. The sea state will influence which way you hedge. In flat water, you can feather into the wind when a puff hits to depower more easily. In a wavy sea state, you have to drive around the waves, so your setup will need to allow a wider groove. 

To simplify the many decisions needed to properly set up your boat, let’s rely on data whenever possible. Your tuning guide for the rig should be scaled to wind strength and sea state. Your homework before the day of racing should include understanding the ranges of wind strength you are likely to see and memorizing or recording the high and low tide times. The easiest but rare days are, of course, those with consistent wind strength. But on days when you get every windspeed possible, it’s helpful to understand where you are at any given moment in the greater trend. Knowing if the puffs you’re feeling are reaching the maximum forecast for the day, or vice versa with the lulls, should help you hedge your settings for the upcoming race. It really helps us decide on the rig setting when we can say something like, “This lull is the lightest velocity we were meant to see, so let’s anticipate a build from here.” 

It is critical for trimmers to identify which sail controls will have the biggest impact. On a hiking or trapezing boat, sacrificing crew weight in the right place to make a control adjustment, like the cunningham or vang, comes with a cost-benefit analysis every time. On the 49erFX, for example, which weighs about 100 kg, the crew’s body weight of approximately 70 kg makes a bigger difference in most puffs than one last inch of cunningham. In an ideal world, control adjustments would happen before the puff or lull hits. But if you get caught out by a puff, before leaning in, ask yourself: Will easing the mainsheet a little more or having the extra bit of cunningham on help us more at this moment? And more so, if the puffs are short-lived, you should not aim for perfection. On high-tempo, transitional days, Steph and I will agree that we are going for 80 percent boat performance, and we both try to find a forgiving and versatile setup on our sheets.  

Lastly, keep in mind that if you’re caught out at the wrong rig setting, it’s likely the majority of the fleet is as well. Don’t let it become a mental distraction during the race. Announce to the team, “We are overpowered; the boat is not going to feel great.” Doing so can help eliminate any distracting input and focus everyone’s attention on going as fast as possible in the moment.

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So many factors go into prepping for a typical around-the-buoys day race: rig tune, sail selection, start line bias, course skew, and currents, but one of my biggest pieces of advice to sailors is to remember to regularly “look up!” One overlooked component of sailing strategy is how the wind behaves around the clouds and by understanding how they can influence wind patterns at the surface, you can gain a competitive edge on the water, especially if you are the only one looking around at the clouds. Clouds are a big topic, of which entire books have been published, but to get you started, here are my five top tips for cloud management. 

Incorporate clouds into your race strategy 

What information can clouds really tell us about what the wind will do in the next hour, next half hour, or even the next 5 minutes? A lot, actually. First, we need to know which clouds we should pay attention to, and which ones we can ignore. This comes down to height, size and shape. Clouds that are low to the surface, have a flat or dark bottom, and/or are puffy in nature are the ones we want to pay attention to. If you see clouds that are changing quickly, getting taller (taller than they are wide) or moving fast, those will also tell you a lot about what the wind is going to do. For example, cumulus (those puffy, cotton-ball-like clouds) over land that are growing taller indicate heating and a strong thermal component to the wind that day, which is likely to be a sea breeze in action. Fast-moving clouds tell you what the winds are doing at the upper levels of the atmosphere. Thin, wispy, or high-level clouds could offer insight as to what the weather will do in the next 12 to 24 hours, but these clouds will not directly impact the wind on your short windward-leeward course. 

On days where clouds are a significant feature of the racecourse, I’ve made checking the clouds part of my pre-race routine. For example, in Miami, where cumulus clouds are routinely moving across the course, I make it part of my routine to look up and check the speed, distance, and height of the clouds every 5 to 10 minutes. Set an alarm on your watch to remind you, just the same way you would systematically check the wind angles and bias on the start line. 

I also check to see how much cloud cover there is across the course, and whether the coverage will change at any point. For example, if the left side of the course has about 40-percent cloud cover (puffy cumulus) and the right side has 20, I will favor the right side of the course (all else being equal) because there is more blue sky in that direction and therefore more of the upper-level winds reaching the surface without being impeded by clouds. 

Avoid sailing underneath clouds

Cumulus clouds are a clear indication of thermal updrafts, which are pockets of warm air rising from the surface. As warm air ascends, it creates lower pressure underneath the cloud, and much less wind at the surface (a relative wind lull). This phenomenon also generates more wind around the cloud’s edges where the air is sinking (relative high pressure) and can provide a puff if you stay on the edge of the cloud—just don’t get stuck underneath it. The best way to get good at reading the clouds, and learning where the edges are, is to practice. It takes experience with many different types of clouds to get really good at nailing the pressure zones and judging the speed at which they are moving

Check for rain

It’s also important to note whether the cloud is actively raining or not, as this will change your strategy dramatically. Clouds that are not raining are as described above, with rising air underneath. Clouds that are raining, however, also have a downdraft near the rain. The strength of the downdraft will depend on how big and intense the rain cloud is. Smaller isolated rain clouds will have a quick downdraft that will flow out from the leading edge of the cloud and provide a small gust of wind as the rain starts initially falling (you usually feel this gust first on the leading edge, or as it is coming toward you.) If you are on the side of the cloud (it is passing to the left or right of you), the wind will tend to shift outward and away from a raining cloud. For example, if a rain cloud is passing to your left looking upwind, you can expect a left shift from the outflow gust.  After that gust, keep clear of the rain cloud because the wind will typically die afterward for up to an hour as the cell collapses, and until the previous prevailing winds return. 

To illustrate this, I’ll use an example from a recent 49erFX Worlds medal race. Pre-race, winds were very light, around 5 knots, and we had many distinct layers of clouds with occasional rain, some clouds were lighter and higher and some lower and darker. In the final minute before the race, winds were barely raceable. Then, I noticed an area of much darker clouds approaching from the left with some spitting rain, and the right side of the course had whiter clouds that were a bit higher up. The darker clouds were approaching fast. I figured they would arrive within the next 5 minutes (just after the race started) and I prayed our sailors (on the US Sailing Team) could see this too. After the start, it was clear they had. They were the only boats going hard left. They got a massive left shift with enough pressure to launch them to the front of the fleet, which had mainly gone right in the old breeze.  With it being such a short racecourse, they were able to hold their lead through two laps and won the medal race. 

Practice navigating cloud-to-cloud
What should you do when you see a few puffy cumulus clouds heading downwind on your race course? Well, if you’re in the Northern Hemisphere, more often than not, the clouds will be moving downwind and slightly right to left across the sky. This is because friction over the water tends to shift the winds on the surface to the left. The winds pushing the clouds are not as affected by friction, and therefore are relatively right-shifted. This would, of course, be opposite in the Southern Hemisphere. For example, let’s say I notice clouds coming down the course on the run, and they are moving faster than I am. I predict they will overtake me and knowing they are moving right to left (looking upwind), I decide to jibe to port to let the clouds pass to my starboard, while I stay under blue skies. 

We can also use this rule of thumb when we see low, flat, blanket-like clouds (stratus or stratocumulus) near or approaching the course. Due to friction, winds under large patches of clouds will generally be lighter and more left-shifted than the surrounding winds under clear skies.

Heed the big-picture forecast

Clouds from synoptic (large-scale) weather systems—fronts for example—indicate a new breeze arriving, if that is expected within the day’s forecast. To illustrate this, I’ll use an example from Miami a few winters ago. The forecast called for a light northerly wind to be replaced by a much stronger northwest wind.  As we sailed out into Biscayne Bay, sailors and coaches were focusing on getting into upwind drills and checking the breeze as it came from the shifty direction of Downtown Miami, where skies were sunny. No one was looking behind us, toward the west. I made it a point to spin around and check for clouds in all directions, as I typically do.

I noted to the coach I was riding with, “I bet the wind will drop in the next 10 minutes and then get ready because it’s going to blow 15 to 20 knots.” As he looked at me, surprised, I just pointed to the horizon where we both saw the clouds and it then clicked—those clouds must be indicating the new wind.

If one were to look at a satellite image from that morning, you would have seen the large cloud bank approaching. But let’s assume you didn’t, and you only knew the wind was forecast to shift and increase. Noticing this cloud bank and how quickly it was moving before anyone else would have made a big difference for your next-race strategy. 

The most accomplished sailors will attest that understanding and utilizing the wind around clouds significantly enhances your strategy. Mastering the wind around clouds is an art that requires a combination of observational skills, meteorological knowledge, and practical experience, so get out there and practice identifying and timing the clouds before your next race. In other words, remember to look up! 

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When the wind gets light and weird, a different approach to the racecourse is required says Racing Editor Mike Ingham. Priority No. 1 is to seek the breeze and from there, play the long game.

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if conditions warrant, some boats, like J/70s, FJs, Collegiate 420s and Snipes, successfully wing for the entire run. And for other boats that carry asymmetric spinnakers, such as J/105s and Melges 20s, brief moments of winging can present gains, such as when jibing, (a late-main jibe), coming into a leeward mark gaining an overlap, or shooting the downwind finish line. It’s a powerful technique to have in your toolbox these days, so let’s dive deeper into the art of the wing, how to do it and when to do it.

There’s usually no ­question when in the middle wind ranges—from 8 to 14 knots—where the wing technique works well. By doing so, you’ll sail less distance without sacrificing much speed, getting you to the leeward mark sooner than someone who reaches back and forth. But in light air, it’s often too slow to wing, and the jib or kite doesn’t have enough pressure to fly well. Also, when the wind is light, the main falls into the middle of the boat, causing an unintentional jibe. You need enough pressure to hold the sails firmly in the winging ­configuration to make it work.

In the crossover zone, when you are unsure if winging will work, it can pay to give it a shot. If it doesn’t feel powered up and fast, abort the wing by continuing your turn, jibing the boom, and flattening onto the new jibe. The cool thing with this move is that you can get a boost of speed during the flatten, especially in a dinghy. Experiment with winging in the crossover wind range, then aborting, ­making it a late-main jibe.

At the other end of the spectrum, when it gets super windy, boats like the FJ, 420 and Snipe are still winging and might even plane on the wing. For heavier boats that wing, like the J/70, there comes a time to abandon the wing and start planing on the reach. It’s all about your best VMG to the mark, knowing your boat, and understanding when to transition as the breeze changes. In puffy conditions in the planing crossover range, 14 to 18 knots, the true masters of downwind morph from one mode to the next, putting hundreds of meters on the competition.

When winging, you must have a big lane behind you because winging is difficult in bad air. Also, boats behind you that are also winging throw a big wind shadow. Always work to find a nice lane before winging. Some people call this a seam in the fleet, a corridor of nice pressure with no boats behind you.

Winging Angles

For those unfamiliar with ­winging and the angle changes created by doing so, one way to think about it is to compare it to a symmetric spinnaker boat, such as an Etchells or Lightning, that can square the pole back in a medium breeze. In light air, those boats reach back and forth with the pole near the headstay. Once the breeze increases enough, they square the pole back and sail deep. This is a similar angle to winging. A boat with the spinnaker squared back is basically the same as being wing-on-wing. When in this mode, you’ll jibe through about 20 to 30 degrees.

I always look forward, toward the gate marks or finish line, to determine if I am sailing the least distance. Visualize your new angle if you were to jibe and question whether it would be closer to the mark. If so, and the lanes are free, do it. Usually when winging, I want to see the leeward mark right over the bow or just between the jib or spinnaker and the mainsail. While doing this, let’s say you get a lift. The jib or spinnaker suddenly feels less powerful, so you head up to get to the optimal angle again with the sheets pulling. Now the gate or finish line has dropped out of your field of vision, behind the main. That tells you it’s time to jibe. Conversely, if you get a big header while aiming at the gate and now appear overstood, abandon the wing and go back to a reach. The key is to point the boat at the gate or finish line in whatever configuration you need to be in for the given wind conditions, assuming you have a good lane.

Tactical Winging

A key to sailing well downwind in any boat is to satisfy two basic rules: Sail the jibe that takes you most directly toward the ­leeward mark, and sail in the most breeze. If you can sail toward the mark while in nice pressure and in a big lane, you’ll hit a tactical home run. When you are in a boat that has various modes, like reaching and winging, always use the most appropriate mode to help you. Here are a few examples:

A. You round the weather mark in a left shift and want to go straight downwind on the header. It’s blowing 10 knots, so winging will provide the best VMG. After rounding the weather mark, you reach for a bit until a lane opens up. Now you have to decide which jibe to be on while winging. You could simply wing on the starboard jibe, or jibe over to port and then wing. Because you are headed and happy, the correct move is to simply bear away and wing, staying on starboard.

B. You round the weather mark in a lift, so the game plan is to jibe to port. But there’s a cone of bad air at the top of the course. You reach for 30 seconds to a minute, eager to jibe and go the other way. With a train of boats sailing straight out of the mark with you, winging away would put you in bad air. So, the best move is to jibe onto a port reach to quickly exit the train of boats and their dirty breeze. Once clear of the bad-air zone, let’s say 50 to 100 meters, go into winging mode to sail the header toward the leeward mark on the port jibe. You’ll be in a nice lane, sailing low and fast toward the leeward gate.

C. You’re leading a tight race or might be just ahead of a group of boats, and you round the weather mark. Don’t immediately wing. If you do, you’ll likely get covered. Here, the move is to round the weather mark, reach for a while, and be patient. Once the boats behind you wing, then you can establish a nice lane and wing. If you reach for a while and feel like you should be winging, but no one around you is, and you want to get away from nearby boats, jibe to port, as mentioned earlier, reach for a little bit to get away from the group, and then wing into a nice lane.

D. If you round the weather mark in a lift and have no boats to worry about behind you threatening to steal your wind, a technique unique to the J/70 is you can get into a wing by bearing away and slowly jibing the boom. It allows you to quickly sail the other way downwind, as if you had completed a full jibe and then winged the kite. On smaller boats that accelerate more during maneuvers, it’s faster to jibe, flatten, and then wing the jib.

Practicing and Speed

Winging well takes practice and communicating to your team about the next move. It’s key that everyone is on the same page. With all the tactical options in the J/70, the fleet has developed its own lingo about turning while winging, “left turn 1 degree here” or “right turn 1 degree,” because up and down can get confusing with sails on both sides of the boat. For winging or exiting the wing in a J/70, identify the sail you are jibing. For example, say, “jibing boom to a wing,” “jibing kite to a wing,” or “exiting wing with boom over and a left turn.” In small boats, it’s a little more straightforward, but communications need to be defined regardless. A few examples are: “Let’s wing here,” “let’s jibe then wing,” and “let’s do a wing-on-wing jibe.” And to exit the wing, “jibing the boom to a reach.”

Sailing fast while winging is critical, so let’s discuss what you should focus on. The short version is, once you have winged a jib or a spinnaker, sail slightly up toward the jib or spinnaker on a broad reach, or a “high wing,” as some call it. You’re trying to not sail dead downwind because it’s faster to be slightly up toward the forward sail in a high wing. There’s a sweet spot, which is where the sail would want to fall in toward the boat and assume a reaching position, if you were to head up a few more degrees toward the jib or spinnaker. If you see that happening, bear away a few degrees until it’s stable and happy. At that angle, the jib or spinnaker will be powered up.

If you’re holding the sheet, you can feel the sail pulling nicely. Bear away a few more degrees to a dead downwind angle and the sail will lose a little pressure. Bear away a little more and you will feel the slowest winging situation possible—by the lee where the sheet pulls the least because the main starts covering the jib or spinnaker. I see a lot of kids doing this in the FJs and 420s, and sometimes adults in the J/70s. You can end up there by turning down accidentally, having a wave push the bow down, or possibly by a windshift lifting you. To avoid sailing too low or two high, stick to the rule of sailing high on the foresail, but not so high that it wants to collapse in on itself. This powered-up mode is fast. To keep it here, you need to constantly test the ups, look at the telltales and masthead fly, and feel the power in the sheet.

If you are at the perfect wing angle and notice a lift (the masthead fly goes from the weather corner of your boat to the center of the stern), the sheet loses pressure, or you just feel like the boat has lost pressure, head up if you want to continue straight. Or immediately jibe to a reach, throwing the boom over, flattening with extra speed onto a header, then bear away and wing again. The jibe maneuver when lifted is super-fast and allows you to quickly sail the header downwind. If performed before others around you, it allows you to lead on the new, long, headed tack. All of this is tactical gold.

Now that you know how and when it’s best to go wing-on-wing, let’s explore seven top winging moves that can make your race.

Cut the corner. Typically, everyone sails out of the weather mark on starboard, reaching, unless conditions call for an immediate jibe set. If you can wing before the boat in front of you, you cut the corner on them and still maintain a starboard-­tack advantage. The boat in front ends up in a difficult situation in that they want to jibe to aim for the gates, but you have borne away inside them and cut them off, and you’re still on starboard. I love using that move in a J/70. I’ve been passed by it, and I’ve passed boats using it.

Be the first to wing. If you round the weather mark with a big enough lead or a gap behind you and instantly wing, you can gain huge on the boats that have not yet done so. Doing that while leading can instantly break the race open. While others are reaching and waiting for the opportunity to wing, you’re already sailing deep, headed straight for the leeward mark, and you’re gone. You can end up winning the race by hundreds of meters. And if you happen to have a gap behind you, winging before the group ahead allows you to cut the corner on them.

Paint the competition into a corner. In the same realm of cutting the corner, this move occurs in the corner, near the layline. Let’s say you’re going downwind, reaching on port jibe, and following someone who is also reaching. As you approach the left corner (looking downwind), knowing they will jibe soon, wing behind them. Now you’re sailing deeper and cutting the corner. When they jibe, you now have a perfectly matched racing setup to jump them and steal their breeze. As the boats converge, watch their masthead fly to see where their wind is coming from, and then jibe over by simply throwing your boom with a right turn and flattening onto their breeze. It’s a quick move and takes the wind out of their sails, literally and figuratively. From here, either you roll them, or they’re forced to jibe back into the corner, reducing their options and forcing more maneuvers. You can also “paint into a corner” against groups of boats.

If in the back of the fleet, wing immediately. Another time to go right into the wing mode is when you’re doing poorly. Maybe you were OCS and went back now to find yourself in last place, desperately hoping to catch up. Wing-on-wing can give you that opportunity. Once rounding in last, you can always lighten the mood by pointing out the good news of having a massive lane, and then instantly wing. I’ve seen a lot of people in that position catch up a ton downwind just by getting into the wing and keeping it the whole run, sailing less distance.

Sail perpendicular. When coming into the finish line or a leeward gate, sail perpendicular to reduce distance. By winging, you cut the corner on any boats ahead that are reaching. I think of it as sailing one side of a triangle while they sail two, by extending forward, jibing and reaching back. You can get to the finish line sooner with this move, even if the wind is a little light to wing.

There is also a specific scenario coming into a gate where you can use it to get room. If you are closely trailing an opponent and both of you approach the gate just outside the zone (aiming at the middle of the gates), you can wing behind them toward the mark to enter the zone first while they extend forward, then jibe to head back and round the gate. You are now inside and have room. Their jibe opens their stern, and you have entered the zone first and inside. This doesn’t happen often, but it feels nice when it does. It leaves you in a much stronger rounding position to start the next leg.

Ping the competition. You’re on the port jibe near the layline, approaching the right-hand gate (looking downwind), and there are other port-jibe boats overlapped to your right. They’re going to have room on you, probably leaving you on the outside of a big pinwheel around the gate mark. In this situation, you can jibe to starboard and reach toward those boats to take them out past the layline, then lead them back clear ahead and rounding ahead. Chances are, they might not anticipate you doing this, but even if they do, they have to stay clear. For safety within the rules, do this well before the three-boatlength zone, maybe as far out as five or six lengths so there’s no question you’re outside the zone. The boats you’re reaching toward can even be winging on the starboard jibe, but they have to either head up or jibe if on port because you’re the leeward boat. In a classic match-racing move, you’ve reached them off the racecourse, forcing them to overstand. They’re typically flailing at this point and probably starting to yell; bear away once you feel the geometry is correct and jibe toward the mark, breaking the overlap with them and entering the zone clear ahead. We call this the ping move. It can also be done at a ­downwind ­finish line.

Vary modes to manage your lane. If you’re wing-on-wing and someone is sailing at a different angle, about to encroach on your breeze, go into reach mode until you find another clean lane. Then bear off and wing again. If you maximize your time in big seams or lanes, you can do some damage downwind.

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Some tacticians like continual input, while others prefer a quiet boat, but the majority of tacticians at least like small amounts of accurate and timely information. In other words, provide the input only when appropriate. Before racing, and especially if you’re new to a team, always discuss the type of information the tactician wants to hear once, and follow these tips after the race is underway to make your input useful.

Sketching Out the Prestart

The tactician will certainly want to know if you spot a last-minute windshift. Indicators are if you notice that you are sailing deeper or higher up or down the line than you were before, or even watching another boat going head to wind or tacking. In a left shift (pin favored) it will take the boat longer to get to the start line. The inverse is also true if there is a right shift or if the boat end is favored. I’ll say something like, “Eyes out of the boat; looks like left shift; it will probably take a little longer to get to the line.” If possible, I’ll add whether it’s a small shift or a large shift.

Traffic is also important to communicate. During the last minute of a start, it is often hard to see everything and everyone. I will often report “shark” or “bogie.” A bogie is someone coming at us that we will have to deal with. Bogies are usually the biggest threat when there’s around two minutes to go and you’re sailing down the line on port. Sharks are boats approaching from behind, like a shark getting ready to bite. When you tack to starboard for the final approach, watch for both sharks and bogies.

The third bit of helpful prestart info can come in the last five seconds. This is where, in all likelihood, the bow person or someone else forward in the boat can let the tactician know if your boat is hidden from the race committee’s view. Sometimes this will let you get your nose poked out in a congested area. Be extra confident with this one, and remember your bow is poked forward of your line of sight. The consequences of getting this one wrong are costly. We only make this call if we are quite sure that boats above and below us are poked well forward and exposed.

Brushstrokes Around the Course

Immediately after the start, you’ll be looking to communicate boat-on-boat relatives. The driver and tactician are looking for comments like, “same speed, higher” or “same height, faster.” With these calls, the trimmers and helmsperson know they are in a good mode upwind. If they hear, “same speed, lower” or “slower, same height,” they know they need to make a change to keep up with the pack.

Where it gets tricky for the person calling the relative modes is when you say things like “faster, lower” or “slower, higher.” In these cases, the commenter must quickly evaluate the VMG and decide if it is a net gain or net loss and make that call. For example, if we are going upwind with a big gap to weather and I say, “Higher, slower, net gain,” the driver and trimmers know that it’s OK to be a little slower because our high pointing is letting us gain on boats around us. The rule of thumb is always talk about your boat when communicating relative speeds and angles. It’s best this information comes from someone in the proximity of the trimmer and tactician so the conversation can be quiet and not too distracting for the rest of the crew.

As we sail upwind, I like to let the tactician know where he is in relation to the laylines. This helps avoid getting too close to a layline from too far away. Many tacticians avoid the laylines early because once you arrive at a layline, your tactical options are limited. This communication also reminds the tactician to start looking at laylines when you’re closer to the mark. I refer to the laylines in percentages with whatever layline we’re headed at stated first. If we are directly downwind of the weather mark, I will say, “50‑50 on the course.” This means that there is equal time to spend on port and starboard before arriving at the weather mark. As we continue up the course on starboard, I’ll look upwind and perhaps say, “30-70.” The tactician will then know that he or she has 30 percent to go to the port layline or 70 percent to the starboard layline. Many tacticians will tack before getting within 10 percent to a layline when they are still far from the weather mark to take advantage of a windshift or leave room to tack back out if you get tacked on.

Calling puffs and lulls helps the tactician decide where to tack, but more importantly, it helps the trimmers and drivers. The trimmers can anticipate and adjust power in the sails, and the driver can pinch or foot slightly to keep the boat tracking properly at maximum VMG. “Short-lived puff in 3…2…1…” lets the driver and trimmers know that only a small change will be needed keep the heel angle the same and the boat sailing along properly. If they hear “more pressure consistently in 3…2…1…,” they will know that a more long-term setup will be required to keep the boat sailing optimally.

RELATED: Downwind Tactics For Planing Conditions

Calling chop and flat spots will help the tactician decide on where to tack as well, but equally important, the calls will help the helmsperson drive the boat. In a choppy section, you often need to foot, and you can really point in flat spots because there is less chop or waves to slow you down. We’ll use verbiage such as “chop in one boatlength,” or “chop continues” or “flat water for a bit.”

Lastly, in some areas, ­calling weed or kelp in the water is important. This can be a little complicated. I like when people keep these communications simple. “Up one, up five, down one, down five” are four of the only six calls I like when I’m driving. If I hear “one,” I know to turn a little; if I hear “five,” I know to turn a lot. I also like to know “clear,” meaning I can go back to driving normally. It can be important to know what mode you are in and where boats are around you. If there is a boat close to leeward, saying “down one” is probably bad when you could have said “up one.” Also, pay attention to boatspeed. Rarely should you say “up five” when the boatspeed is already low. The final two calls are “no lower” or “no higher.” This simply lets the driver know that he can stay on course as long as he doesn’t turn toward the debris.

As with upwind, calling puffs on the downwind leg is important. When soaking, the helmsperson and spinnaker trimmer can work together to make some gains. For ­example, if they know that a puff is coming, they can soak deep a little longer. Normally, after soaking deep, you have to head up to build speed. But if you know a puff is coming quickly, you can stay deep and let the puff help you accelerate rather than heading up and burning distance.

The tactician will likely want to know whether they are in clear air or not. This also helps the spinnaker trimmer. I will often call how many boatlengths of clean air we have. For example, I will say something like, “We have three lengths of clear air,” meaning there is bad air from a competitor three lengths behind us. Then later, if I say we have two lengths of clean air, everybody knows that we need to speed up or sail slightly higher to avoid bad air. Then if I say, “One boatlength of clear air,” the crew knows we are in danger of being rolled.

The rule of thumb is always talk about your boat when communicating relative speeds and angles.

Again, like upwind sailing, it helps to communicate relatives between boats. In some boats, such as the Etchells, the bow person can look behind and make these calls, almost becoming the boat-on-boat tactician themselves. If the trimmer, who is ideally talking to the driver about angles, hears “lower, slower, net gain,” they know their mode of sailing slower but lower is gaining on the competition and they can continue sailing in that mode. However, if they hear “lower, slower, net loss,” they know they need to change modes to achieve a better VMG. The tactician may be interested to hear “lower, slower, net even.” This means that you are simply sailing a different mode, but you are not gaining or losing overall. In this case, the tactician can decide how they want to sail for future positioning. The tactician may want to sail low and slow across someone’s bow so that after a jibe, they are again in clear air.

Last but not least, as you come into a leeward gate or finish line, the tactician can benefit from input on which end or mark is favored. Remember, it is OK not to have all the answers. However, even that should be communicated. Don’t be afraid to say, “I don’t know.” It’s better than giving false information.

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The inclusion of a distance-race offering was hatched in earlier years of the Helly Hansen Sailing World Regatta Series, with a goal of getting idle boats and crews off the dock, on to the water for one day, and into the party after racing. Simple enough, right?

Right, but is one day ever really enough? No way. If you’re going to dial up the crew list, order the sandwiches and strike the dodger, you might as well get another day of fun, right?

Right. At all Helly Hansen Sailing World Regatta Series stops this year, organizers are offering two days of distance racing (or what could be more aptly called long-course buoy racing, as there is no overnight element), where competitors enjoy a daylong race that tests the boat and its crew on all points of sail, across a variety of winds and conditions.

One of the best parts of a long-course race is that when the Sailing Instructions state the warning signal will be at 1000, you can bet you’ll be starting your wrist top timer at 1000. There will be no race committee chatter about whether the windward mark is perfectly in place for an erratically shifting morning breeze. Nope. with long-course racing, when you get the course, you know your marks, you get set, you go.

Managing the long-course action this year, as he did in 2022, will be Annapolis-based race officer Bruce Bingman. The plan, he says, is to start the long-course fleet 5 to 10 minutes before the big-boat one-designs on his circle, to send them on a 6- to 16-mile random-leg challenge and finish them right where they started—or perhaps somewhere else. We checked in with Bingman to pick his brain on what to expect and how best to conquer the unpredictable Chesapeake Bay.  

What sort of courses can our distance-race competitors expect?

Of course, it all depends on the wind strength and direction, but the way I normally do it is to send all the boats up to the same weather mark, maybe a mile or so directly upwind, and then after that, judging that we’ll set up near the red bell buoy off the entrance to the Severn River——about 3 miles out from harbor—I’d probably send them to Eastern Shore, around a few markers there with some beats, headsail reaches, some downwind work, and a jibe or two. Then come back around a box; roughly speaking so we get all compass legs if at all possible. I always try and think of interesting courses that we could do and I typically set them assuming that we have the prevailing southerlies or the post-frontal northerlies.

How many times can we expect to cross the current? Which can be a big deal.

At least twice. My intent is always to give people an interesting race. To get to the Eastern Shore you’ll have to cross it going over and obviously again coming back. I will, however, set up a few courses for the lighter breeze where they won’t cross the current because even on a light current day the current will run up to a knot in the center of the bay. If there’s been heavy rain, up in Pennsylvania or Northern Maryland, and they open the flood gates, you’ll get 3.5 knots of current running down the center of the bay.

Can you share some of your wisdom as it pertains to distance racing in this part of the bay?

I always run with both a knot meter and a GPS, as well as the boat’s compass. You want to make sure you’re optimizing all the way around. On a distance race, you always have to be thinking about optimizing VMC—that’s velocity down the course, not necessarily velocity directly to the mark. Part of the thinking of that is that if it’s long enough of race and you know the wind is going to shift during the race, and if you’re beating to the mark and another competitor has been just cracked off and going faster than you, they will be further down course, even though they may not be directly downwind of the mark. They’ll be further toward the mark than you are, so when the windshift comes, they can take advantage of the shift. They’ll either tack and lay the mark or be lifted toward the mark. I’m very much a VMC racer provided it’s long enough. You can’t do that on a one or two-mile leg, but once it gets over 2 miles, you really need to be thinking about what the wind will do. Look at clouds—obviously you want to sail to the dark cloud. Try to improve your chances the longer the distance gets. The shorter the leg, the more you need to focus on VMG, and that’s all about optimizing sail trim and boatspeed. When it comes to distance racing, I try never to pinch unless I have a very good reason.  

What are your thoughts on dealing with the current?

The further you get to the center of the bay, the strong the current is, so you don’t want to get caught short going around a mark in the middle of the bay. That last tack of 50 feet will cost you a lot more than over-standing by 200 feet of the mark. If I’m tacking for the Hackett’s Point can, for example, and the current is flowing down the bay and I’m in light northerly (going up the bay), I will wait until the thing is 45 degrees off my transom before I tack.

How about some more tips on racing in Annapolis; If you were racing, what would be your priorities?

Lots of water. Not beer, until after the race. I spend a lot of time looking at the weather and being really confident on which sails I will want to use and which ones come off the boat. For sure you want to make sure you’re prepped and have an outboard lead of some sort so you have a better slot to control for headsail reaching because you will almost certainly do some headsail reaching. If you’re rounding the mark and rigging up outboard leads, you’re too late. That’s not fast. If I’m going to run a staysail, I’ll make sure that’s set up and ready to go. Change sheets should be ready and available. Practice. If you can, before the race, get the crew together and practice some headsail changes and a spinnaker peel. It’s an opportunity to get out there and shake the cobwebs.

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When approaching the ­leeward gate, there are a lot of possibilities to consider: Which mark to round? How to best round it? What’s the exit and the next windward leg plan? All of this needs to be discussed on the run so your overall game plan is clear well in advance. It’s much easier with a single leeward mark, in which case you can jump ahead to the next ­section—the approach—and focus on techniques used for rounding the left-hand gate, which is likely what you’re doing when there is only one leeward mark. But when there are gate marks, things get complicated, and the tactician has a number of factors to consider. Let’s start by defining your choices.

Closest and most windward mark: If the gate marks are in place before the start, it is usually possible to sight them with a hand-bearing compass and then determine the wind direction that would make them square (add or subtract 90 degrees depending on which way you sighted). The mark that is farther upwind should be closer, similar to the favored end of the starting line.

Most favored from where you are: The mark that is farthest upwind (or highest ladder rung) might not be the most favored from where you are in the moment. In other words, if you approach from one side of the course or the other, the mark which you can round soonest is probably favored for you.

Least crowded: This is important, especially if you’re stuck in a pack of boats.

Cleanest air: With the approach and the exit looking upwind, consider where the ­fewest obstructions and the best wind will be. One good test of the favored-gate mark is when two boats round opposite marks simultaneously and continue on opposite tacks. After the fleet is cleared, if both boats tack, the boat that is ahead probably had cleaner air and perhaps rounded the favored or closest mark.

Most advantageous current: Rounding the down-current mark will usually make an easier and faster turn. However, there may be tactical or strategic advantages to the up-current mark. When the current is running across the course—i.e., from one gate mark toward the other—it’s usually best to round the down-current gate (the mark toward which the current is running) because the rounding will be easier and the boat will get there faster due to the movement of the current.

The Final Approach

The goal here is to work hard to be the inside or farthest ahead boat. One way to do so is to stay out of the “no-go zone” in the middle. Approach one of the gate marks from outside the funnel and maintain boatspeed while avoiding bad air.

We learned about the no-go zone the hard way at an Etchells Worlds. We were caught back in the pack (50ish in a 90-boat fleet) and stuck smack in the middle of the funnel, with boats pouring in from both sides. The race committee had set the marks so close that there were less than six boatlengths between them, which meant the three-boatlength zones for each mark overlapped. We intended to round the left mark, but boats to the left of us were telling us to turn right for the right-gate mark while boats to the right of us, who also wanted the left mark, were telling us to turn left for the left mark. Eventually, the funnel overfilled and the whole group converged, locked rail to rail with no one able to turn. The lesson here is to prioritize being inside—with rights, of course.

Approach the three-boatlength zone with the most speed possible to obtain or break later overlaps. It’s imperative to be vocal if you have rights, or if another boat does not have rights and is trying to take inside room. The observation moment for whether an inside boat obtains an overlap and therefore has rights to room inside is when the leading boat of your group that is overlapped and rounding together reaches the three-boatlength zone. If you have been overlapped or not overlapped with another boat for a minute or more as you approach the leeward gate marks, and it suddenly changes, be sure to let the other boat know you have either broken the overlap or established it as soon as that occurs. And remember, Rule 18.2(e) (Giving Mark-Room) says: “If there is reasonable doubt that a boat obtained or broke an overlap in time, it shall be presumed that she did not” (obtain or break the overlap before the first of the two boats reached the zone).

If a boat tries to establish a late overlap to windward of you, your best defense is to luff them above the three-boat-length zone, and then bear off sharply to break the overlap and get your bow into the zone. This defense works well on both port jibe to the left gate and ­starboard jibe to the right gate.

A common ­mistake is getting pinned beyond the laylines when both boats are outside the zone. Rule 18 (Mark-Room) does not apply until one of the boats is in the zone, so it’s important to understand the nuances of the rules in this situation.

And here’s a quick tip on spinnaker handling when approaching the zone: Count down the drop for the crew to hear. Usually, the tactician will provide a 30-second warning and then a 10-second countdown. Once the count is established, the pit, crew boss or bow person should also voice the countdown. For boats with string takedown systems, the sheet is released (slacked) sometimes as late as 2 on the countdown.

The Strategic Rounding

Once we’ve decided which gate mark we want and where we want to go on the second beat, we have to manage and optimize the rounding strategically. Let’s first tackle the standard reaching approach, which is by far the most common and generally regarded as the easiest method.

Some types of boats may require a brief bear away to unload pressure on the spinnaker and facilitate its drop. So, we need to reach into the mark a little high of the layline, allowing the time we need to finish the bear away, and then head up to a fast reaching course.

Another approach is to jibe around the left-gate mark (aka the “Mexican”). Here, we come in, usually at a hot angle, on starboard with rights until reaching the protection of the three-boatlength zone, where the mark-room rule begins to apply. The spinnaker is usually coming down on the left side of the boat, and a wide jibe rounding makes the douse easy for the crew. The douse is ideally left so late that the boat is already jibed and on port jibe, so the spinnaker falls on the new windward (port) deck.

We perfected Mexican drops on the TP52 Spookie using a string takedown system. The crew trained me to pause the turn, nearly dead downwind, as soon as the boom jibed. At that moment, the chute was dropped onto the port (and now windward) deck. It was ­counterintuitive at first, but it worked so well, I readily adopted the technique. We proceeded to mimic the maneuver with a new name for the right-gate mark called the “Rodeo” drop. That way, the crew always knew exactly what type of drop and rounding to expect. The Rodeo goes like this: We’re on port jibe and want to go around the right-gate mark. We stay wide outside the funnel to ensure an inside overlap at the zone and jibe onto starboard around the mark. The spinnaker is still coming down on the left side of the boat. The Rodeo differs from the Mexican in that the spinnaker will end up to leeward.

A third approach—the “Flop”—is a specialty maneuver for certain asymmetric-rigged boats that is used when you can’t quite lay the mark without jibing, but don’t really want to complete a full jibe. A similar technique can be used on symmetric spinnaker boats, possibly by removing the pole and trimming the sheet and guy outboard by hand or foot. The Flop should only be attempted in moderate winds, flat water and clean air. It does not work in light or heavy winds. In light air, there simply is not enough wind pressure to keep the spinnaker full; in heavy air, it can become unstable and hard to handle, and lead to a ­spectacular wipeout.

When flopping, the boat goes wing-on-wing, meaning the main and asymmetric sails are flying on opposite sides. Ease the tack line by 15 percent of the boatlength as you bear away to by the lee to encourage the asymmetric to fill, and then return to slightly above a dead-downwind course. A successfully performed Flop is a very sharp arrow for your quiver and should be practiced to perfection. There are several variations of the Flop, and it is possible to jibe either the asymmetric or the mainsail. We have even tried a “Double Butterfly” by jibing both the main and asymmetric at the same time. I have never seen it attempted before—or since—and I wouldn’t recommend it again, but it did work.

Executing the Rounding

With approach determined, the next focus is the execution of the rounding. Here’s where we need to address the term “seamanlike.” When the inside boat does not have right of way, it is only allowed enough room to make a seamanlike rounding of the mark (see the definition of “room”), which is a smooth, curved rounding that maintains speed and stays within a boatlength or so from the mark.

The next term to remember is “tactical.” When the inside boat has the right of way, it can make a tactical rounding, which basically means “swing wide and cut close,” all the while keeping maximum speed.

One of our options during our rounding is to intentionally slow down once we reach the zone. A brief slowdown can pay big dividends if it improves your rounding, especially if you would have been forced to the outside of the boat ahead had you maintained your speed. You always want to round behind boats you are giving room to and round close to the mark. The slowdown can be achieved by taking the spinnaker down early, overtrimming the mainsail, or weaving with the helm (using your rudder as a sort of brake). When and how much to slow the boat is an art form ­practiced by team racers.

On rare occasions, we might plan to tack around a leeward gate mark. This is usually a bad idea because it sends us straight back into the funnel, with its attendant bad air and confused sea state. The main reason to tack around a leeward gate mark is to take advantage of a windshift, especially if you have just made a big gain and are unsure it will continue (and may perhaps oscillate back the other direction, thereby ­negating or reducing your gain).

In special circumstances, it’s better to round outside of an inside boat we are giving room to; this we call “Round the Outside” (or “Buffalo Girl”). This move helps ensure we can punch out, getting our bow forward of the inside windward boat. This approach works only if we have our bow well forward of the inside boat as we approach the mark and are ­confident we can maintain a safe leeward position. The technique is simple: Keep speed up by making a more gradual rounding than the inside boat, which might have to do a sharp head-up, causing it to slow. If the inside boat sails over and blankets you, it’s game over. It’s a high-risk move, and if it goes bad, it usually results in losing several more boats rather than the one you tried to get around.

The Exit Is Equally Important

The goals coming out of the gate include the following modes: fast, maximum VMG and boatspeed, with sails always correctly trimmed. As you round, the main must be trimmed ahead of the jib to add helm, thus reducing the amount of rudder angle needed for the turn.

Clear wind: Use your approach with reaching speed to coast slightly high of closehauled in order to hold a lane for as long as necessary while the tactician executes the exit plan. The tactician might want to hold high of the bad air from the boat(s) ahead by pinching in order to keep clear air to either maintain a lifted tack or continue toward the favored side of the course. Or the plan could be to tack as soon as the downwind traffic clears out. It’s rarely advantageous to foot through to leeward of the bad air from the boat(s) ahead.

Advantaged: If the gate you chose is favored (more upwind), then you should be able to tack and cross a boat that rounded the other gate. But just being ahead is not enough reason to tack. You need to continue on the lifted tack, heading toward the favored side of the course, and with clear air.

The ideal exit is all about ­flexibility, having the ability to tack when and if we want to, or just go as fast as possible and execute your strategy like you’d planned it on the run.

Rules at the Leeward Gate

Let’s now have Dave Perry, author of Understanding the Racing Rules of Sailing, take us through the roundings:

When two boats are overlapped as they enter the zone of a leeward gate mark, the inside boat will either be the “keep-clear boat” (windward or port-tack boat) or the “right-of-way boat” (leeward or starboard-tack boat).

An inside keep-clear boat is entitled to “mark-room” from the outside boat under Rule 18.2(b) (Giving Mark-Room), which is room to sail to and around the mark in a “seamanlike way” (see definition of “room”). If it stays within a seamanlike course, it is exonerated by Rule 43.1(b) (Exoneration) if it breaks Rule 10 (Port/Starboard) or Rule 11 (Windward/Leeward). Typically, that means the inside boat needs to stay closer than a boatlength away from the mark throughout its rounding. It is not entitled to room to make a “tactical” swing-wide or cut-close rounding.

On the other hand, an inside right-of-way boat can sail wherever it wants to, subject to a couple of limitations. Because it is a right-of-way boat, it does not need the protection of mark-room. Furthermore, Rule 18.4 (Jibing), which requires inside right-of-way boats to jibe around single leeward marks, does not apply at leeward gate marks (see the second sentence of Rule 18.4). Typically, inside right-of-way boats sail a tactical swing-wide or cut-close rounding. But with no Rule 18.4 at a gate mark, an inside right-of-way boat can sail farther from the mark than its proper course and delay or attack ­outside keep-clear boats during their roundings.

However, there are two ­limitations on how aggressive an inside right-of-way boat can be at a leeward gate mark:

1) If it became the leeward boat from clear astern, Rule 17 (On the Same Tack; Proper Course) applies and requires it to sail no higher than its proper course. Typically, but not always, when a boat enters the zone of a gate mark, it is fastest to round that mark. In that case, the leeward boat would need to jibe when its proper course was to jibe to round the mark.

2) Anytime a right-of-way boat changes course, it has to give the keep-clear boat room to keep clear under Rule 16.1 (Changing Course). If the right-of-way boat is changing course away from the mark, it is not sailing within the mark-room to which it is entitled, and so it is not exonerated by Rule 43.1(b) if it breaks Rule 16.1.

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