2025 Courageous Sailing Annual Flip Flop Regatta
August 9
The Flip Flop Regatta is a fun and competitive race for all – one of the largest New England regattas of the season – a pursuit style race starting in Broad Sound, looping around the outer harbor islands, and finishing in inner Boston Harbor! The Flip Flop draws a 50+ boat fleet, all racing in support of Courageous Sailing’s mission of transforming children’s lives through sailing programs that inspire learning, personal growth, and leadership. Whether you’re a regular on the regatta circuit or a member of the Flip Flop’s Liveaboards and Wannabe Pirates class, the Flip Flop is a spectacular day out on the water, for an incredible cause…as you can see from these photos of the 2024 event. And after the regatta, as the sun sets over Charlestown, racers and landlubbers alike gather under the big tent on Pier 4 for music, drinks, bites, and good times.