A Practical Guide to Sailing St. Thomas

A Practical Guide to Sailing St. Thomas

St. Thomas is a nautical lover’s dream, with sailing schools, an international regatta, champagne catamaran cruises and plenty of other reasons to set sail By: Natalie Compagno
<p>The steady winds around St. Thomas make it a great sailing destination. // © 2015 Dean Barnes/St. Thomas International Regatta</p><p>Feature image...

The steady winds around St. Thomas make it a great sailing destination. // © 2015 Dean Barnes/St. Thomas International Regatta

Feature image (above): Professional sailors visit the island for the annual the St. Thomas International Regatta. // © 2015 Dean Barnes/St. Thomas International Regatta

The Details

American Yacht Harbor

Bad Kitty

Cyoa Yacht Charters


Island Yachts

Island Sol

St. Thomas, with its reliable winds and laid-back nature, is a favorite destination for professional sailors and fans alike. Watching the brightly colored spinnakers in the St. Thomas International Regatta — as they catch the breeze and the vessels tack back and forth — is a nautical lover’s dream.

Vacationers can experience this exciting environment just like the pros. With friendly lessons and a plethora of rental options, St. Thomas is the perfect place to plan a sailing escape.

For the expert sailing enthusiast, look to American Yacht Harbor in Red Hook. The marina offers friendly and informative service and can refer sailboat rentals, charters and more. Restaurants and shops along the marina provide all the necessary amenities. Besides sailing, there are fishing, diving, and luxury day-trip options. If a bareboat charter is optimal, sailors might want to refer to the website and reserve a vessel in advance.

One of the best things about St. Thomas is its prime location within easy sailing distance to other islands. Visits to St. Croix, Jost Van Dyke, Tortola and Anegada combine to create excellent seven- to 10-day sailing holidays.

Cyoa Yacht Charters has been curating nautical trips since 1980, and the company works with customers to choose the best itinerary and budget, with or without a crew. Island Yachts is also a veteran yacht rental company, and if visitors become enamored with their boat, the company can help facilitate a possible purchase. 

Pro tip: Be sure clients have their passport if they want to voyage to the British Virgin Islands or other non-U.S. destinations.

For a stress-free way to enjoy the azure waters of St. Thomas, take a boat tour with a charter company, and let someone else steer the day away. But for a personal excursion, Daysail “Fantasy” is an exclusive sailboat great for day trips. Rum punches, a hot Caribbean lunch, snorkel and fishing gear plus private swimming locations are all included. The St. John Champagne Catamaran takes seafarers on a half-day sail to St. John and provides snacks and, of course, champagne. Another option is Bad Kitty, a catamaran day cruise with breakfast, an open bar and a great itinerary. Another plus: The boat’s stability is good for kids.

The beauty of St. Thomas is an ideal backdrop for sailing lessons. There are many to choose from, but a good place to start is Virgin Island Sailing School or Fair Wind Sailing School. For a real insider experience, take a lesson or book an eco-adventure with Paul Stoeken of Island Sol. He is an active member of the U.S. Virgin Island sailing community and races in the St. Thomas International Regatta.

For a complete seagoing adventure in the U.S. Virgin Islands, stay at either The Ritz-Carlton, St. Thomas for its proximity to the Yacht Club or Secret Harbour Beach Resort for the enthusiastic sailing excursions that leave right from its dock.


To rub shoulders with local mariners, lunch at Hook, Line and Sinker for delicious daily catches and a buzzing vibe. It’s always happy hour at The Tap & Still in Vessup Bay, where young and old take advantage of the cheap beer and excellent burgers. For dinner, try Sunset Grille for its atmospheric beachfront dining and upscale seafood dishes.