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One of the most popular pursuit races in New England returns in 2020!

August 8th, 2020


Register Here!

Dear Friends,


The 2020 Flip Flop Regatta is ON!!!! Please join us Saturday August 8th for one of the largest pursuit races of the year, starting in Broad Sound, around the Outer Harbor Islands and finishing in Boston Harbor. Registration details and NOR are now posted on www.regattaman.com .


Due to COVID-19, we will not be having a post-race party this year, but we will have an online awards ceremony on a date to be announced - stay tuned. 


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, becoming a Skipper 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 would still like to donate to help Courageous, click here. Your 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 August 8th.

Best Regards, 


Dave Alexander

Flip Flop Regatta Chairman


Dave DiLorenzo

Executive Director



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Thank You to Our 2019 Supporters and Participants!

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 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.

We have tons of pics from the race and party and are setting up a gallery soon. In the meantime, check our FB and Instagram pages for a preview!

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


Enjoy the Photo Galleries of the Event

On-the-water Gallery

Party Pics
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Many thanks to Avi Levy and Bill Shea for these great shots!
Here are the links you can share with your crew:

Bill Shea Photography
Aviran Photography

Please support their great work by purchasing the pics you like.
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More party pictures can be found here.

2019 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