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Sailboats anchored in Vessup Bay in St. Thomas in the U.S. Virgin Islands
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    U.S. Virgin Islands

With balmy breezes, azure waters and plenty of nearby islands, St. Thomas is an ideal destination to explore by sailboat.

Approaching St. Thomas by air, you’ll first notice the line of islands stretching to the east, separating the Atlantic Ocean from the Caribbean Sea. Look closely, and you’ll spot protected coves sprinkled with moored sailboats. Once you land on St. Thomas, plan to book a sailing excursion – it’s the best way to experience the enchanting Caribbean waters of the U.S. Virgin Islands. Feel the wind in your hair, hear the waves lapping at the bow and watch the islands pass slowly by. This is the island life!

Choosing the Best Sailing Experience

There’s something wonderfully romantic about seeing the trade winds fill a boat’s bright-white sails, powering it through deep-blue waters past lush, mountainous islands. The U.S. Virgin Islands are blessed with fabulous sailing conditions year-round, so making that dream a reality here is a breeze. Day sails are the most popular option for visitors to St. Thomas, with weeklong charters another way to immerse yourself in the sailing lifestyle. Some visitors try out a day sail and love it so much that they book a week-long charter for their next vacation.

For day sails, you’ll have three options: Join a group sail, book a crewed sailboat for your group or, if you’re an experienced sailor, rent a sailboat and head out on your own. Should you decide to book a week-long charter, you’ll have three basic options: an all-inclusive charter (they come with a captain and a chef), captain-only or what’s known as a bareboat charter (where you sail the boat yourself). Any of these possibilities will give you a great opportunity to get out on the sea and explore the islands.

Heading Out on a Day Sail

Full- or half-day sails are the easiest way to get out on the water, and since many day sails accommodate just six guests, you’ll get personal attention. You may be able to board a boat right from the dock at your resort. Relax on a dinner sail out of Marriott’s Frenchman’s Cove, near Charlotte Amalie, or a champagne sunset cruise out of the Ritz-Carlton, on the island’s east end.

Adventurous travelers will enjoy a combination sailing and snorkeling outing. Among the options are excursions that leave from Yacht Haven Grande, near the busy cruise ship dock, or a marina near St. Thomas’ east end. Explore the waters of Buck Island National Wildlife Refuge or the pristine bays of St. John and look for tropical fish, majestic sea turtles and graceful rays. Snorkeling equipment and assistance are included, as are lunch or snacks and drinks. Visitors looking for a flatter ride might want to book an excursion on a catamaran – a sailboat with two hulls – rather than a monohull.

Out for a sailing trip with a local St. Thomas charter

Out for a sailing trip with a local St. Thomas charter
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Dean Barnes

Taking the Helm

If you’re an experienced sailor, you and your group might consider renting a sailboat and exploring the clear waters and protected bays around St. Thomas on your own. Leaving from Charlotte Amalie Harbor, you can sail past the cruise ship dock, through Long Bay and past Hassel Island with its extensive ruins. Head to Water Island, the largest island in the harbor, drop an anchor off Honeymoon Beach and steer your dinghy into shore to relax on the white-sand beach with a tropical drink in the shade of a coconut palm. Sail back to the mainland to grab lunch or dinner at Tickles Dockside Pub or an ice cream cone from Scoops & Brew, both in Crown Bay.

If you pick up your sailboat at Compass Point Marina or another East End location, sail to Christmas Cove, off Great St. James Island, just to the east of St. Thomas. It’s a popular spot for snorkeling and grabbing a slice or a whole pie from Pizza Pi, a floating food truck.

If you’ve always wanted to learn to sail or you want to brush up on your sailing skills, check out the St. Thomas Sailing Center, located in the St. Thomas Yacht Club. You can sign up for learn-to-sail or advanced sailing courses there.

A beautiful day for sailing in St. Thomas

A beautiful day for sailing in St. Thomas
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Getting There

Nonstop flights to St. Thomas’ Cyril E. King Airport are available from New York City, New York; Atlanta, Georgia; Miami and Orlando, Florida; and Charlotte, North Carolina; and there are plenty of connecting flights through San Juan, Puerto Rico. Once you land, you can rent a car (remember to drive on the left!) or take an open-air taxi, known as a safari, around the island.

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