The Labor Day Regatta

On Labor Day weekend, hundreds of sailors from across the U.S. and Canada point their bows toward City Island for the 78th Annual Labor Day Regatta, September 5–6 — the Sarasota Sailing Squadron’s biggest weekend of the year and, by the Squadron’s count, the oldest continuously held regatta in the Southeast.

Sailing since 1946

The first Labor Day Regatta went off in 1946, back when the Squadron was a scrappy young club on the bayfront. Seventy-eight editions later, it’s one of the longest-running traditions Sarasota has — a fixture that has outlasted almost everything else on the water.

What the weekend looks like

Racing runs both days across five separate courses on Sarasota Bay, with sailors ranging in age from 8 to 80. The regatta draws around a thousand visitors each year, and the Squadron wraps the whole thing in a proper party: a Friday night welcome gathering, a Saturday dinner at the club, and an awards ceremony Sunday. This year the fun stretches into Monday, too — the second annual Parrot Head Regatta caps the weekend on Labor Day itself.

How to watch

The action is centered at the Sarasota Sailing Squadron on City Island, 1717 Ken Thompson Parkway — past Mote on the way out to Longboat. Spectators are welcome, and the Squadron grounds and the bayfront both offer good sightlines to the courses. Bring a hat and settle in; when a few hundred sails are up at once, Sarasota Bay is about as photogenic as it gets.