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


August 6th


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:

Register on Regattaman

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

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

2021 Entertainment Sponsors


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Make-A-Mark Partnerships

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Live & Silent Auctions

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

Download the Auction Donation Packet
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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
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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