Join Us for the Flip Flop Regatta - Boston Harbor's Favorite Pursuit Race

The annual Flip Flop Regatta is one of the largest New England regattas of the season - a fun and competitive pursuit-style race that starts in Broad Sound, loops around the outer harbor islands, and finishes in inner Boston Harbor! Each year 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. After the regatta, as the sun sets over Charlestown, racers and landlubbers alike gather under the big tent on Pier 4 for music, dancing, drinks, bites, and good times. Join us in 2027!

2026 Highlights:
Another fantastic day of racing on August 8th! Shifting breezes (flip flopping, perhaps?) kept things interesting for the 59 boats on the course, the competition was tight, the Party on the Pier was an awesome chance to connect, and it was all in support of free sailing programs for kids!

Congrats to our winners!
Class A: Pressure Drop in 1st (and overall winner!), Vanish in 2nd, WildThing in 3rd
Class B: Virgo in 1st, Cloudbreak in 2nd, Hope in 3rd
Class C: Mysterious Ways in 1st, Special Sauce in 2nd, Kodiak in 3rd
Class D, J80: Fins in 1st, Bliss & Ella in 2nd, Amigo in 3rd
Class F: Freckles in 1st, Man of War in 2nd, Impromptu in 3rd
Pirates and Liveaboards: Artemis in 1st, Lyra in 2nd, Vespera in 3rd
Sportboat: RockIt 2.0 in 1st, Wild Ride in 2nd, Velox in 3rd

Shout out to Bliss & Ella and Defiance, co-winners of the Spirit Award!

Thanks to our regatta sponsors!
Admiral Level: Dave Alexander, Bryan Lee, Richard Tubman, Brian Barmmer
Captain Level: Dave + Tom Powers / Joe Crimmins, Renee Bushey and Bill Jacobson, Eric Mongeau, Mike Kostigen and Stephanie Muto, Peter Isaacson, Lance Ryley
Helmsman Level: Dan Boyd, Mark Fitzgerald, James Gardner Long III / Ryan Wagner

Thanks to all who sailed, donated, volunteered, and made the day so much fun: Dave Curry and Doug Ryan of Hull Yacht Club for the RC boat and support, Nate Peterson and the whole Courageous team, Lance Ryley for the ratings wizardry, Gerry for keeping the music hopping, Constitution Yacht Club and Savin Hill Yacht Club, and so many more.