The windward mark is a literal and figurative turning point in almost every race, so it’s important to approach the mark smartly and have a good rounding. As you get closer to the mark, there are many things you can do to help improve your chances of success. Here is a brainstorm list of some to consider. Of course, it won’t be possible to do all these things all the time. In fact, if you’re sailing a single- handed boat, you might do only a cursory job on a handful of these items. But when you’re racing a 50-footer, you may do a fairly complete job on almost everything.

The key here is to divide up the responsibilities among your crew, since one person can’t do every- thing. For example, put one person in charge of looking for the next mark. Let the helmsperson focus 100% on speed if possible, and make sure you have good communication so he or she receives all the important information.

Confirm that you are heading for the correct mark. We’ve all gone to the wrong windward mark, and it’s not a great feeling. Worse yet, most of us have gone to the wrong mark even when someone in our crew knew it was probably wrong (but assumed the skipper knew what he or she was doing).

To prevent this, verbalize which mark you are going to well before you get there, and make sure everyone in your crew agrees.

Make sure you’re planning to round the mark in the correct direction. OK, the good news is you rounded the right mark – but the bad news is you went around it the wrong way. This could be almost as bad as heading for the wrong mark, so prevent mistakes with good communication. Before you get to the mark, say “We’re going around this mark to port,” and be sure no one disagrees.

Determine your final tactical approach. As you get closer to the windward mark, it becomes more difficult to avoid other boats and maintain clear air. So before you get stuck in a bad position, take a good look at the boats around you. Should you approach the mark on starboard tack or port? When do you want to get to the layline? What’s the best way to maintain a lane of clear air? Factor all these into a plan that will get you around the mark as quickly as possible.

Watch the roundings of the boats ahead of you. There’s a lot you can learn by watching the boats in the fleet ahead of you or the lead boats in your fleet. For example, if there’s current, are they having a hard time getting around the mark on starboard tack? This info could make a big difference in how you approach the mark.

If you’re racing on handicap, take the times of boats ahead of you when they round the mark. Compare these to your own time and figure out how you’re doing with them in the race. Knowing where you stand can be helpful in deciding your strategy and tactics.

Locate the next mark visually. Unless you have poor visibility or bad eyesight, this is an absolute must. Assign one crewmember to find the jibe mark or leeward mark before you get to the windward mark. Look for easy ways to identify the mark location. For example, before you reach the windward mark you might tell your skipper, “On the next leg, aim for the tall smokestack on land over there.” Knowing this location early will help you figure out where to point your boat right after the mark and may also be useful in planning your strategy for the next leg.

Figure out a compass bearing for the next leg. If you have a compass, try to calculate a course to steer for the second leg of the race. This is especially useful when it’s difficult to see the second mark. If you are using fixed government marks, plot your course on a chart. If the race committee is set- ting marks, you can figure out the second-leg course if you know the bearing to the first mark and the course geometry. For example, if the first mark is set at 185° and you have a 90° turn at the jibe mark, your course on the first reach will be 050° (185° minus a 135° turn at the windward mark).

Predict your angle of sail on the next leg. Well before you reach the windward mark, figure out your apparent wind angle for the next leg. If you’re going onto a run this is easy, of course. But when the second leg is a reach, determine how tight it is so you’ll know if you can carry a spinnaker. The easiest way to determine the angle of sail is by watching boats ahead that are already on the second leg. Are they all carrying chutes? Are any of them having problems? If there are no boats on the next leg, use geometry to figure out your wind angle.

Talk over your strategy for the next leg. Just as you should develop a first-leg strategy before the start, you need to devise a strategy for the second leg before you round the windward mark. This doesn’t have to be too complex; it could simply be something like, “We’re going to jibe set and play the left side of the run where there is more wind,” or “Let’s delay our spinnaker set so we can get up high in the passing lane on this windy reach.” In order to come up with a good strategic plan, you must look ahead to the next leg while you are still sailing up the first beat. Obviously, it helps to do this a few minutes before you reach the windward mark, since moves like a jibe set require a bit of preparation.


When you approach the first mark, it’s easy to get distracted by everything that’s happening. There are usually lots of boats around, for example, and it often seems like half your crew is getting the chute ready. However, when you are distracted, most likely you aren’t sailing your boat too quickly. Therefore, as you get closer to the mark, it’s very important to stay focused on maintaining speed, especially for the helmsperson and sail trimmers. © Stephen R Cloutier


Get your spinnaker ready. If you will be flying a chute on the second leg, get it ready so you can hoist as soon as you round the windward mark. Some things you may need to do before the mark include uncleating the halyard and sheets, setting the pole and moving the spinnaker to a hoist-ready position. Think ahead and perform some of these tasks on your last port tack before the mark. Otherwise you may have to move to leeward to accomplish them, which is not too good if it’s windy.

Review your crew’s spinnaker set procedures. This is something that you have hopefully done in practice sessions or before the start of the race. However, it doesn’t hurt to offer a few reminders just before you round the mark and hoist. Focus on a few key points that will make a difference. For example: “Bill, you have the spinnaker sheet, right?” and “Sarah, remember to ease the jib out when we hoist,” and “Joe, don’t forget to push the pole forward to the clew.” A few calm words like this can help keep things organized and smooth.

Note any race committee signals. Keep your eyes out for race committee boats. It’s possible they might shorten your course at the first windward mark, but I’ve never seen this. More likely is a change of course if the wind has shifted and the second leg is a run. In this case, take note of the bearing to the new mark and try to locate this mark visually (it probably has a special feature like a band). Factor its position into your strategy for the next leg.

Work hard at going fast. Speed should be a priority all around the race course, especially at a critical point like the first mark rounding. If you have good speed, it will make tactics and boathandling that much easier. While everything in this brainstorm list is important, don’t let it distract you from going fast.

If you’ve done a good job on most of the things listed above, then you will be well prepared to round the mark and sail a fast, smart second leg. Of course, when you round the mark, there is another whole list of things you should be doing. This includes looking at the current on the buoy, recording your time, punching in the mark’s GPS position, finding the next mark again, going fast and so on. ■

This article originally appeared in David Dellenbaugh’s Speed & Smarts, The newsletter of how-to tips for racing sailors. If you want to sail faster and smarter, log onto

A resident of Easton, CT, Dellenbaugh was tactician and starting helmsman for America3’s successful defense of the America’s Cup in 1992. He’s a Lightning World Champion, two-time Congressional Cup winner, seven-time Thistle National Champion, two-time winner of the Canada’s Cup, three-time Prince of Wales U.S. Match Racing Champion, and a winner of the U.S. Team Racing Championships for the Hinman Trophy.