One of the most popular pursuit races in New England returns in 2022!

August 6^th

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!

Your entry fee and all proceeds support Courageous Sailing's youth programs and further our mission of transforming children's lives through sailing programs that inspire learning, personal growth, and leadership.

Becoming a Skipper Sponsor is a great way to support Courageous by potentially doubling your contribution! If your employer has a matching gift program for qualified 501(c)(3) nonprofit organizations, submit the receipt from your Sponsorship along with the completed sponsorship form (download from the information page) to your company. Details are on the entry page on Regattaman here:

If you are unable to race but you or your crew would still like to support Courageous: Donate here

Due to the emergency repair work on Pier 4 taking place this summer, we won't be able to host our usual big bash, but we are trying to organize a post-race gathering elsewhere - please stay tuned for details.

Your participation and donation will help Courageous be there for the kids who need our programs more than ever in these difficult times, especially while our pier is being repaired.

Thanks for your continued support, and hope to see you on the race course Sat. August 6th!

Best Regards,

Dave Alexander

Flip Flop Regatta Chairman

Dave DiLorenzo

Executive Director

Notice of Race

Our Other Annual Regattas

Thank You to Our 2021 Supporters and Participants!

We’d particularly like to thank our in-kind sponsors:

@Mount Gay Rum
@Sam Adams
@Triple Eight Distillery
@Polar Beverages
@Peak Event Services
@Cisco Brewery
@Spindrift Beverage Co.
@Pig Pig BBQ
@Renaldo’s Pizza
@Lord Hobo Brewing
@Petit Vin

Our individual sponsors:

Admiral Sponsors
Mike Dresse – Tooth Face
Constitution Yacht Club
Dave Alexander – Pressure Drop

Helmsman Sponsors
Betsy McCombs - Scherherazade
Thomas Curtis - Magpie

Captain Sponsors
Ed Redmond - Wind Tango
Lance Ryley - Rockit 2.0
Chris Zibailo - Dopodomani
Pauline Dowell - Konik Morski
Steve Clark - Red Herring
Dave Franzel

...and our photographers:

Bill Shea, Larry Andersen, Morgan Nankivell, Avi Levy, and Dave Waller of Grave's Light for allowing us to shoot from the lighthouse.

Lastly, our sincere thanks to all of you who came out to race and party afterwards. Your participation helps Courageous transform children’s lives through sailing programs that inspire learning, personal growth, and leadership.

Dave Di Lorenzo
Executive Director

Dave Alexander
FFR Chairman