Welcome to the 2026 Flip Flop Regatta Information page.

Welcome to the 2026 Flip Flop Regatta! 

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 60+ 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. 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. 

All regatta entries include 2 tickets to the party. Additional party tickets for crew can be purchased online through Eventbrite for $40 ($10 off) with discount code crew2026. Each ticket includes post-race chowder and 3 drinks.

ALSO NOTE: Any boat that does not currently have an ORR-EZ rating will be provided a provisional one-day rating. Boats without ratings must sign up by August 4 in order to obtain a rating.