Expand your mind by mixing it up

Published on July 29th, 2024

When the sport shifted to primarily racing around only a windward and leeward mark (what lap are we on now?), the variety in course charts was replaced by repetition. While this ‘perfect race course’ may be great for World Championships, Robert Harris reports on how they are mixing it up in Southold, NY:


Fifty-four years ago, several sailors sat on the beach at the Southold Yacht Club (SYC) looking across at Shelter Island and mused “wouldn’t it be fun to race our 14-foot-long Sunfish around the Island,” and thus the “World’s Longest Sunfish Race” (WLSR) was born.

The 53rd edition was held July 20, with the race start and finish at the SYC, and the 26-mile course circumnavigating Shelter Island for a singles fleet and a doubles fleet. Sixty-seven boats participated with 74 sailors which included seven doubles, making this one of the largest WLSRs to date.

The direction of the circumnavigation (clockwise or counter-clockwise) gets announced at the Skipper’s Meeting, which proved to be counterclockwise around Shelter Island because of the wind and tide.

Sailors ranged in age from 16 to 76 and hailed from as far afield as Nevada, Georgia, and Australia. It is a very competitive race and one of endurance; just finishing is an accomplishment. After a rough day on – and in – the water, a double dose of Advil after racing hits the spot!

Starting in light wind, a building breeze had the final leg gusting to about 18 knots, with winner Chris Williams finishing in just over 4 hours 44 minutes and most of the fleet completing the course within the 6-hour time frame.


Racing around islands provides problem solving unlike any sausage course, with dynamic features that keeps the mind thinking from start to finish. Try it… you might like it.

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