Three Islands.

Three Days.

One Adventure.

December 5 - December 8, 2024

The U.S. Virgin Islands is a territory of different islands, divided by water.

We think that the same ocean that divides us can also bring us together.

The Three Sheets Regatta is a sailing event that traverses the waters between St. John, St. Croix, and St. Thomas. Celebrating each island, competitive sailors and weekend cruisers will participate in a truly unique Virgin Islands event.

New Sailor or Old Salt, we hope you will join us.

Maybe you see yourself more of a cruiser than a racer. Maybe the one thing that you know about sailing is that you don’t know enough about sailing. Whatever the case, the Three Sheets Regatta offers a new way to experience these islands and the cruising community around them. Make it a race or make it a journey — this one is open to all.

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A regatta for everybody.

Thursday night registration and kick-off celebration is at 5:00pm on November 30 in Coral Bay, St. John at The Salty Mongoose Pizza & Rum Bar. We raise sails early Friday the 1st for the trip south. It is almost 40 nautical miles from Coral Bay to the Christiansted area where the Club Comanche Hotel on St. Croix will host the sailors and race events and activities. Saturday, explore St. Croix, rest, and recharge for the final leg. Early Sunday, we are at it again, sailing north to end in St. Thomas. We’ve also scheduled a fun event at The Box Bar — just to be consistent. See the Schedule of Events for details.

Join us for good food, friends, drinks, boats, culture, and love!

Three Ports, Three Days

ROARING 20s PRODUCTION, INC.

is a Virgin Islands not-for-profit corporation whose mission is to foster an international amateur sailing competition in the Territory. 

Our mission is also targeted to help educate the next generation of local sailors in the sport. 

We aim to bring together visitors, islanders, and USVI businesses in a weekend of fun and activities as we explore the islands and open waters between St. John, St. Croix, and St. Thomas. 

Join us in celebrating these green islands and the sparkling blue waters in between.