One of City Island Yacht Club’s most popular races always takes place in September, toward the end of the all-too-short sailing season. The Sayers Series, potentially the longest-running race in CIYC’s history, is named after past commodore Henry Sayers who started the club’s “Family Day” races sometime in the late 1940s.
Sayers managed the Family Day races for several years, and as the story is told by a few current club members, Sayers would give each boat in the race a rating he thought it should have, not the rating determined by traditional methods.
Today’s Sayers Series carries on the spirit of the original family day races from which it was born, explains Rich Coar, CIYC member and owner of Chaika.
“It’s a big social event. It’s an opportunity for people who don’t race that often to see what their boat can do,” says Coar about the Sayers Series and why all members should partake.

CIYC Members David Zedlovich (R) and Rich Coar (L) sat down for a drink after sailing to tell the story of the Sayers Series.
This year’s Sayers Series is scheduled for Saturday, September 23 and as is tradition, the first race in the morning is a lap around the buoys and then members come back to the club for lunch. The afternoon race, around Hart Island, is a test of knowledge about the currents, the tide, rocks, and the wind. Coar has managed the race since 1983 when he was Regatta chair at the time, and he describes the much-anticipated event as “anybody’s race to win.”

Pictured above from left to right: the Sayers Series trophy, made in 1911 as CIYC’s first trophy for its annual regatta. Engraving detail reads: “The Regatta committee of City Island Yacht Club at their first annual regatta, held June 18, 1911, presented to Gertrude K, winner of the trophy.”; the Sayers Series invocation written by Brad Stone, former CIYC Commodore; photo of the Gertrude K, recipient of the trophy in 1911.
Members who have participated year after year agree. It’s not only the perfect race for a beginner sailor to get a taste of racing, cruisers and experienced racers also appreciate the less competitive nature of the race. The Sayers is also different in that it has a pursuit start, meaning each boat has a rating assigned, the slower boats start first and the faster boats “pursue” them.
“You don’t start with a whole bunch of other boats and then get your handicap taken off at the end,” Coar explains. “The advantage of having the boats start on their handicap rather than all start together and take the handicap at the end is it doesn’t spook people at the start and when you’re doing results, all you’ve got to do is see who came in first, second, third because the handicap is already there.”
It’s Anybody’s Race
So which is the boat to beat this year? Coar is quick to answer. “Anybody could win it,” and names some obvious and not-so-obvious past winners: Ernie Bivona on Eagle and another member who won it with a cat boat one year. But this year’s defending champ is Chru Brar, owner of Bibi.
The real challenge Sayers presents is the choose-your-own-adventure approach for the afternoon race around Hart Island. Participants can go either way around but must utilize some navigation skills to steer clear of the rocks known as “The Blouses” and “No Nations.”
The Sayers is also the only race at CIYC with an actual invocation, written by Brad Stone when he was Commodore from 2010–2012. The prose of which teases both the cruiser persona and the racer persona in all of us: “I ponder if my boat’s a fit, with all the gear I’ve put on it” and asking, “How can I lose, is this a trick?
“It’s not a trick,” Coar insists. “The Sayers Series is the one race you don’t want to miss.”
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