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One of the most popular pursuit races in New England returns in 2019!

August 10th, 2019

Courageous Sailing, Pier 4

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Regatta Registration

Join the regatta! Registration includes after-party tickets.

Sign Up Now

After-Party Tickets

Join the party after the regatta, no sailing required.

Purchase Tickets

Join one of the largest NE regattas of the year — a pursuit race from Broad Sound, around the Brewster Islands and back to the finish in Boston Harbor. After the race, join us for one of the best harbor-side parties of the summer at Courageous Sailing Center on Pier 4 in the Navy Yard. The Mount Gay Tent party will be in full swing from 6:00-10:30PM, this year featuring live music from Hot Mess, drinks, food and awards. Everyone is welcome!

Courageous Sailing is host of the Flip Flop Regatta. All proceeds will support Courageous Sailing’s youth programs and further their mission to transform children’s lives through sailing programs that inspire learning, personal growth, and leadership.

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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