Ahoy, Matey! Grab the Helm at These Caribbean Sailing Schools


Sailing is a way of life in the British Virgin Islands. (Photo: Gus Estrella/Flickr)

There’s something effortlessly enticing about the Caribbean sailing lifestyle—barefoot days spent swimming and sunning, sundowner cocktails at island dive bars, falling asleep to the gentle rock of the waves, and the simple pleasure of wind hitting your face and salt spray cooling your body as you heel through the water on nature’s power (no carbon footprint). Plus, it’s warm there, winds are generally benign, and in many top sailing destinations you can always see land.

Water isn’t exactly in my blood — I grew up in the desert and remember seeing the ocean twice in my childhood — but I was seduced by this world as soon as I stepped into it. I happened to be in Antigua during the big-deal regatta there and found my way to the wheel during a chase-the-race cruise and rudimentary lesson. I didn’t get the physics, but man, I loved the feeling.

Related: How to Become an Urban Sailor: San Francisco and Beyond


Feel the wind in your hair during a sailing trip in the British Virgin Islands. (Photo: Thinkstock)

A couple of years after that, I was seduced by a yacht captain, whose appeal, I later realized, had a lot to do with the fact that he’d thrown over a corporate job after looking out his office window at the sailboats below and deciding he wanted to do that instead. Things fizzled quickly but got me thinking: If this whole writing thing doesn’t work out, maybe that’s my next act. Or at least I should start learning — I didn’t want the boy, but I wanted the adventure.

So I jumped at the chance to become the first student in Peter Island Resort’s learn-to-sail program last month. The luxe private-island resort, one of those old-school Caribbean gems, recognized that a lot of guests watch the boats anchor off Deadman’s Beach and their occupants roll into the beach bar, and they feel more than a little envy.

The resort paired with the Rob Swain Sailing School, based on nearby Tortola, to offer a luxury-swaddled version of the U.S. Sailing Association’s Basic Keelboat course. A textbook comes in the mail before your trip (you’re well advised to start studying it in advance), and the course unfolds over three days: two with an hour or so of classroom instruction, followed by four hours of practical work on an IC24 (24 foot) keelboat with a tiller and then a third day for review on the water.


All of those ropes and sails have a function — who knew? (Photo: Kansasphoto/Flickr)

It’s relatively basic stuff — vocabulary, right of way, tacking, jibing, trimming and easing sails, a man-overboard drill that incorporates many skills — but enough to take an exam and (hopefully) get Basic Keelboat certification and a one-year membership in U.S. Sailing.

Most people don’t feel prepared to take out a boat solo after three days of instruction, and I’m among them. But Peter Island’s gentle introduction — complete with a cushy room and delectable meals — hooked me in further. I’m already dreaming about when I can take my next class.

Want to learn how to sail? Here’s where to start sailing in the Caribbean.


Learn basic keelboat sailing at the Rob Swain Sailing Academy. (Photo: Rob Swain Sailing Academy)

Rob Swain Sailing Academy, British Virgin Islands

Former racer Rob Swain has taught sailing in the Caribbean for more than 20 years, and his team of skilled, safety-conscious instructors is top-notch. Accredited by the American Sailing Association (ASA), the school offers basic keelboat (learn how to sail), live-aboard cruising, cruising catamaran, and more advanced and customized classes that lead to certificates from the U.S. Sailing Association. Guests can book directly with RSSS and stay anywhere in Tortola (or on the boat, for more advanced classes).

Related: The Most Chilled-Out Caribbean Spots — Ever


Learn the ropes at Barefoot Offshore Sailing School. (Photo: Barefoot Offshore Sailing School)

Barefoot Offshore Sailing School, St. Vincent and the Grenadines

This ASA-accredited school encourages students to start off with a more intense course, a weeklong live-aboard sailing immersion that includes navigational theory, course plotting, galley cooking, and other skills not covered in a three-day class. BOSS trips include overnights (on the boat) and dinners (on the boat or local restaurants) in the Grenadines’ most beautiful islands. Weekend intro courses and women-only programs are also offered.


Learn how to sail a yacht while you visit the British Virgin Islands. (Photo: Ondeck Maritime Training)

Ondeck Maritime Training, Antigua

Being in one of the most British of the islands, this school is aligned with the Royal Yachting Association, whose credentials are good on any British-flagged ship, and most others as well. The intro class is a weekend RYA Start Yachting course, which is geared toward novices and counts toward the next class, the five-day Competent Crew program. Ondeck director Pete Anthony says, “We get a fair number of single ladies who end up getting hooked and doing regattas with us in different parts of the Caribbean.” (I may become one of them: My first experience was with Ondeck.)


You’ll learn how to sail and get a great tan. (Photo: Horizon Yacht Charters/Facebook)

Horizon Yacht Charters, Grenada, British Virgin Islands, Antigua, St. Maarten, the Grenadines

Horizon promises “first-class, [ASA supported] tuition on first-class yachts in some of the most idyllic cruising grounds in the world,” and enough pleasure — anchoring every afternoon to snorkel, fish, sunbathe, or drink like sailors — to call it a learning vacation.


A sailboat at Abaco Rave, the Bahamian boat race. (Photo: Photoshirl/Flickr)

Abaco Sailing, Bahamas

The only ASA-accredited sailing school in the beautiful, easily accessible Bahamas offers courses from Basic Keelboat on up to Advanced Coastal Cruising.

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