Dear Friends:
The 2025 Flip Flop Regatta was the one we’ve all been waiting for: perfect wind, perfect weather, a spinnaker run all the way down the channel and across the finish line, and an awesome party featuring live music from Neon Lighthouse to finish out the night. Best of all: 65 boats in the fleet, from regatta regulars to first-timers sailing in the “Liveaboards and Wannabe Pirates” class! Thanks to all who made the day possible, and congrats to our winners:
Class A: Agora
Class B: Uproarious
Class C: Tonga
Class D: Mysterious Ways
Class F: Pinchy, leading the fleet to the finish line for the overall win!
Liveaboards and Wannabe Pirates: Artemis
Spirit Award: Defiance
We’re so grateful to these racers for donating in support of the event and the Courageous mission!
Fleet Philanthropists and Sorcerers of the Seas:
Mike Kostigen and Stephanie Muto, Lyra
Admiral-level Sponsors
Dave Alexander, Pressure Drop
Bill Jacobson, Vanish
Bryan Lee, Hope
Richard Tubman, Charisma
Captain-level Sponsors:
Tom and Dave Powers / Joe Crimmins, Agora
Lance Riley, RockIt 2.0
Eric Mongeau, Defiance
Peter Isascson, Uproarious
Mark Fitzgerald, Tonga
Helmsman-level Sponsors:
Dave Franzel, Spring
Crew-level Sponsors:
Robert Bova, Phoenix
Charlie Burckmyer, Cloudbreak
Supporter-level Sponsors:
Gordon and Antonina Parris, Moonlight
Bill Finn, Sparklepony
Guillermo Narvaez, Artemis
Thinking about joining the fun in 2026? 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, dancing, drinks, bites, and good times.
2026 registration and party ticket information will be posted in the spring. Hope to see you there!
Sincerely,
The Flip Flop Regatta / Party On The Pier Committee
Dave Alexander, Flip Flop Regatta Chairman
Dave DiLorenzo, Courageous Sailing Executive Director
Thank you to our sponsors!
