One of the most popular pursuit races in New England returns in 2021!




Dear Friends,

The Flip Flop Regatta is back for 2021!!!! FFR is one of the largest NE regattas of the year - a pursuit race starting in Broad Sound, around the Outer Islands and back to the finish in Boston Harbor. The race will be held in accordance with state and local health mandates. 

A post-race party and awards ceremony will be held on Pier 4, featuring Sould of Boston and DJ Ryan Brown! Food and drinks will be available for purchase from Big Pig Barbeque. Please check back on this website, Courageous Sailing's website and Facebook pages for updates.

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.

If your boat is racing or your interested in supporting the event, becoming a Sponsor is a great way to help 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 at Regattaman.

If you are not racing but you or your crew would still like to donate to help Courageous, click here. Your participation and donation will have a huge impact and help Courageous be there for the kids who need our programs more than ever in these difficult times.

Thanks for your continued support, and hope to see you on the race course on Saturday, August 7th.

Best Regards, 

Dave Alexander

Flip Flop Regatta Chairman

Dave DiLorenzo

Executive Director


Thank You to Our 2021 Supporters and Participants!

Become a 2021 Sponsor
A list of our 2021 sponsors is coming soon, until then we're taking a look back at our 2019 Sponsors: The 2019 Flip Flop Regatta was a smashing success! We had outstanding weather, almost 50 boats on the race course, and an epic party afterwards. To top all that off, together we raised more than twice the amount vs. last year, all proceeds going to the programs that do so much for Boston’s kids. A big shout out to everyone who worked hard to make it such a great day - our volunteers, Courageous staff, and Race Committee. 

We’d particularly like to thank our in-kind 2019 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 2019 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


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