Should I Stay or Should I Go: A Sailboat Racing Lesson Learned


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UK Sailmakers International’s Adam Loory actively races his own custom 40 foot sailboat. After racing he writes about lessons he’s learned or relearned. Here is his latest installment. 

Should I Stay Or Should I Go

The turning point of last week’s evening race happened on the second leg of the three-leg race, which was a 3.6-mile run. In the middle of the leg there was an island with a long lines of rocks parallel to the course on either side of the island. We had to make a decision on which side to pass the island within a mile after going around the windward mark. We were the third boat in our division to round the windward mark so we wanted to defend AND attack. 

We were a couple of boat lengths behind our nearest competitor (who owed us 12 seconds per mile) and the lead boat was probably 10 boatlengths ahead. Not long after the rounding, the leader, who owes us 36 seconds per-mile, jibed away from the two of us slower boats opting for the other side of the island. At first it looked like he jibed into less wind, but after he jibed back he had good speed. Some in our crew wanted to jibe over and follow the leader; but I made the call to stay with the boat closest to us who we were beating it on corrected time. If we jibed away, we could loose both boats.

Many times in the past I have been tempted to make tactical maneuvers by what appeared to be better conditions; but I have learned to stay with my competition instead of going after gains that may or may not materialize, particularly in handicap races. 

My decision to not jibe paid off. We took bites to leeward and got a couple of boat lengths lower than the boat ahead of us and, when the layline neared, our tactician called the jibe perfectly and we made the turn to the last mark before the boat we were following. As a result, we led him to the leeward mark and finished ahead.

As for the boat that seemed to be making gains after she jibed — the faster boat — her luck ran out and we rounded the leeward mark about the same distance behind as we were at the windward mark — no gain after 3.6 miles. At the finish, we corrected over her by four minutes. 

Lesson learned: Know who your competition is, stay with them and don’t fall prey to thinking the grass is always greener on the other side of the course.

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