Dear Friends,

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. 

We lucked out on weather for the 2024 Flip Flop. The rain cleared, the sun came out, the breeze kicked in, and 52 boats sailed an awesome regatta! And the 400+ of us who celebrated afterwards couldn't have asked for a more gorgeous night for our first Party on the Pier back on Pier 4! Flip Flop is very much a community effort–huge thanks to our Principal Race Officers Alexe Taylor (Courageous Youth Program Director) and Karen Tennenbaum (US Sailing Regional Race Officer); Bill and Dar Collins of Hingham Yacht Club for providing the race committee boat and loads of support; to Richard Tubman, Gregg Nourjian, and Dave Alexander for all their hard work on so many fronts; Larry Anderson, who took these fantastic on-the-water photos; DJ Ryan Brown; sponsors Mount Gay Rum, Sam Adams, and Maine Craft Distillers, and the generous skippers listed below.

Congrats to our class winners, overall winner Agora, and spirit award winners Vanish and Pinchy!

Class A: Vanish in 3rd, Orion in 2nd, and Scylla in 1st

Class B: Idaho in 3rd, Never Settle in 2nd, and Agora in 1st

Class C: Mashnee in 3rd, Hope in 2nd, and Sparkle Pony in 1st

Class D: Tempest, in 3rd, Kodiak in 2nd, and Mysterious Ways in 1st

Class F: Harrier in 3rd, Pinchy in 2nd, and Froya in 1st

Pirates and Live-Aboards: Seaweed in 3rd, Cheers in 2nd, and Sea Scarab in 1st

We’re so grateful to these racers for donating in support of the event and the Courageous mission!

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

Helmsman-level Sponsors:

Dan Boyd, WildThing

Mark Fitzgerald, Tonga

Dave Franzel, Spring

Linda Hosking, Ares

Peter Isaacson, Uproarious

Crew-level Sponsors:

Lars Carson, Plover

Don Gillespie, Houdini

Stephanie Muto and Mike Kostigen, Lyra

Shawn Whalen, Whale N’ Sea

Dave Alexander, Flip Flop Regatta Chairman

Dave DiLorenzo, Courageous Sailing Executive Director