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Your premier sailing destinations.

From the Caribbean to New England, select your choice for training and chartering from four of the most remarkable sailing venues in the world.  

Tortola, BVI

The BVI offers the most consistently ideal sailing conditions for learning to sail. Trade winds blow on the norm from ten to twenty knots throughout most of the year. More important than wind speed is the wind direction. The wind blows almost constantly from the east down in the Virgin Islands. That makes for much easier learning - sailing out of our channel into the Sir Francis Drake Channel the wind will be blowing on your left ear as you look ahead. Repetition is the key to learning sailing, and the wind helps us here enormously. The Sir Francis Drake Channel is approx 9 miles long and 4 miles wide. Blocking the Atlantic Ocean is the island of Tortola, and shielding us from the Caribbean Sea swells are eleven other islands. This geography makes for the perfect training ground - a lively 2-3 foot chop and constant trade winds. It is very sunny here (about 85 degrees), but the winds keep it comfortable.


Your experience with Swain Sailing School will be a great learning endeavor, and your trip to Tortola in the British Virgin Islands will be unforgettable! Contact us for more information regarding sailing lessons and bareboat catamaran and monohull charters in the BVI.

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Jamestown, Rhode Island

Swain-Rhode Island is located in beautiful Jamestown Village on Conanicut Island.  A short drive from downtown Newport, our location in the New England Sailing Center offers a friendly, welcoming community in the coastal town of Jamestown.  


This lovely mariner's town offers wonderful restaurants, great shopping and the perfect venue to start and finish your sail training or charter.   



Antigua’s shoreline is washed almost exclusively by the Caribbean Sea and is hugged by 95 miles of superb coastline. The islands are best known for their friendly and welcoming people, pink and white-sandy beaches, crystal clear waters and the most satisfying and enjoyable climate in the world.


Red Hook, USVI


The picturesque coastline around Red Hook features beautiful bays and superb snorkeling. 

Set on the East End of the island, the town of Red Hook is known for its stunning beaches. Swim in the sheltered waters of Nazareth Bay on the south of the island or walk north from town for 20 minutes to discover pristine white sand and coral reefs at Sapphire Beach.

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