Join us for one of the most popular pursuit races in New England! 


August 12, 2023   

Stay tuned for 2024 date and registration.  

Dear Friends,

The Flip Flop Regatta is a fun and competitive race for all - one of the largest NE regattas of the season - a pursuit style race starting in Broad Sound, around the outer harbor islands and back to the finish in Boston Harbor! 2023 marked another spectacular day out on the water, with 49 boats racing in support of Courageous Sailing's mission of transforming children's lives through sailing programs that inspire learning, personal growth, and leadership.

Congrats to our class winners: Pressure Drop, Agora, Mashnee, Morris the Cat, and the festively edecked Endeavor (also winner of the Spirit Award)! Pics are available here
Many thanks to our volunteers & staff, Hull Yacht Club for providing the RC boat and able crew, and to everyone who participated, especially our very generous skipper sponsors. We're so grateful to have the Boston sailing community come out in force to support our Courageous kids - see you next year! 
The Courageous Flip Flop Regatta Committee

Dave Alexander, Flip Flop Regatta Chairman

Dave DiLorenzo, Courageous Sailing Executive Director

Thank You to Our 2023 Supporters and Participants!

We’d particularly like to thank our in-kind sponsors:
Mount Gay Rum 
Pier 6 Restaurant


Our individual sponsors:

Admiral Sponsors 
Mark Fitzgerald
Bryan Lees 
Dave Alexander
Richard Tubman

Captain Sponsors 
Aeneas Dodd-Noble 
Tom and David Powers / Joe Crimmins 
Ed Morris
Lance Ryley
Anthony Warren

Helmsman Sponsors 
Dan Boyd
Dave Franzel 
Bill Jacobson
James Long

Crew Sponsors 
Don Gillespie
Lars Carlson


...and our photographer:

Luke Boelitz


Make-A-Mark Partnerships


Live & Silent Auctions

Generous donors provide a wide range of auction items. 100% of proceeds benefit Courageous Youth Programs.

Download the Auction Donation Packet

Food & Drink Donations

Each year, Boston-area catering and beverage services provide delicious tastings, refreshing cocktails, and a selection of beer and wine.

Download the Food & Drink Partner Packet

Make-A-Mark Partnerships

Individuals and companies can directly support Courageous Kids this year by making a financial contribution at Make-A-Mark.

Download the MAM Partner Packet

Event Information