6 Steps to Winning Regattas

Want to win your next big event? Don't overthink the problem, just follow these simple steps and you'll be well on your way.
big fleet
In big fleets like Key West Race Week, it can seem impossible to get to the top. These six steps will help you climb the ladder. Photo by Sara Proctor.

1. You Don’t Have to Win the Start

Let’s face it, the start is the hardest part of any sailboat race. It is easy to mess up, and if you do it is an almost sure fired way to have a bad race. If you go big and decide that you have to win the pin or the boat, recognize that in a crowded scenario usually only one boat is going to come out with a great start. The rest of the pack will be slow and struggle for the first couple of minutes. Better to start a little away from the fray, say 1/4 or 1/3 of the way from an end with space and room to leeward especially early in the regatta. A good start is one that allows you to go straight for 3-4 minutes without being forced to tack. Many moons ago I was sailing in a 20+ fleet of One Design 35’s. On many of Key West racing circles the left side is favored in prevailing conditions. Win the pin, beat feet to the left and win the race. Of course it didn’t take very long for everyone to figure this out which made starting at the pin to go left nearly impossible. (Made more difficult by our own lack of competence). Our tactician (local Annapolis sailor Mark Hillman) came up with an unusual winning strategy. We started on port, ducking as much of the crowd as we had too, went 200 yards and tacked. Now we had clear air and a lane to go left. Relying on the slow pace of the clump struggling off the pin, we were able to roll over the lot and get to front row on the left.

2. Don’t Make the Big Mistake

Key West is, for most of the classes, a no “throwout” series. You can’t make the big mistake and win. The big mistake is usually a foul, so no matter how easy you think the cross on port is, or how much room you are sure you have to tack in front on the layline, don’t do it if it is close. Losing a couple of boat lengths playing it safe is a winning strategy. There are lots of other ways to make big mistakes, here are a couple of regulars…

3. If You Are Not Sure About Which Way to Go Stay With the Fleet

Hopefully you get out to the race course an hour early, sail extensively upwind and down to get compass numbers and develop a feel for what the wind is doing. You should have a plan of attack for the first beat. However, you don’t have to go all in, particularly early in the regatta. There is nothing wrong with sticking with the bulk of the fleet, especially with the boats that you know are probably going to be a factor. If the fleet splits equally, work to win your side but don’t be afraid to be the first to lead back to the middle to check in. The thing to avoid is the classic big mistake, being the furthest boat in the corner. The only exception to this might be in very light air and unstable conditions where the winner will probably have to play a side hard.


4. Take Down Early

If there is a big mechanical mistake to be made it will come at the leeward mark. The bottom mark rounding is by far the most difficult maneuver to get right, and it is the one where the downside risk to getting it wrong has the highest penalties. Don’t get the spinnaker down and go whizzing past the mark, or worse yet have your helmsperson compound the problem but turning upwind with the spinnaker still wrapped around the rig, and you will lose big time. So, when in doubt, particularly if it is windy, take it down early. Worse case scenario is that you are a little too prepared for the turn up to close hauled and give away a boat length or two on the front side. You will probably gain it back with a cleaner acceleration and exit from the mark.

5. There Will Be One Race…

That makes or breaks your regatta. It will not be the one where you get the perfect start, hit the first shift, and win by a mile. No, it will be the one where you make the big mistake. The trick is to remember, when you are rounding the first mark in last place, that if you struggle back to a mid fleet or better finish, that will be the difference for the series. Don’t try to bang a corner and hit a home run. Continue to do the right thing, be patient, and grind them down one boat at a time. Good chance that the back markers will be fairly easy to get past. When you finish 10th congratulate the team and let them know that they just made the most important effort of the event.

6. If You Want to Win a Big Regatta… Go to lots of them!

A final thought for you as you go in search of your first big podium finish. The famous sailors you see consistently mentioned in the media go to a lot of regattas. Your odds go way up. You will be remembered for the three or four top finishes you had that year, not the 10 or 15 where you had average results.