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Learn to Sail: A Review of Caribbean Sailing Schools

Updated: Jul 17, 2022

Picture yourself aboard a barefoot sailboat, learning offshore sailing, diving, and discovering secluded Caribbean beaches on your sailing vacation. Sounds amazing right?

Whether you are wanting to learn to sail with your significant other, solo, or family sailing vacation, consider the Caribbean for your next vacation.

As we researched many sailing schools in the Caribbean, we reviewed the American Sailing Associations (ASA) website to see which schools were licensed to instruct and provide certification to travelers wanting to learn sailing.

Therefore, we have put a guide together for Caribbean sailing schools for you to begin your sailing adventure!

No Experience Necessary

Remember, you do not need to have experience with sailing to go on a sailing vacation where you learn to sail.

Caribbean Sailing Vacation Schools

The Barefoot Offshore Sailing School sounds like a great sailing vacation to us! They offer many ways to become a certified sailor, but one course that stood out to us was the Catamaran Learn-n- Cruise Course. It's a week-long sailing course where you liveaboard a catamaran and learn to sail while cruising the Grenadine Islands. They also set aside time for snorkeling, diving, and offshore experiences. Can you picture yourself learning hands-on sailing techniques aboard a catamaran in the Caribbean? We can!

LTD Sailing is located on the Island of St. George in the Caribbean and they offer various certification courses. This sailing school has the whole package for an amazing sailing vacation. They offer seven-day liveaboard sailing certifications where you learn basic sailing on a monohull or catamaran sailboat. We were excited to read that they offered boats no more than five years old and that their catamaran selections were impressive. With LTD Sailing's example itinerary, you may want to extend your seven-day sailing school to a ten-day sailing vacation while anchoring off-shore, exploring islands, and snorkeling in the most beautiful parts of the world.

The Virgin Island Sailing School is located on the island of St. Thomas, U.S. Virgin Islands. Their seven-day liveaboard sailing courses are tailored to meet your needs. We enjoyed reading about their Series 1 course where you earn your ASA 101 (Basic Keelboat Sailing), ASA 104 (Basic Coastal Cruising), and ASA 104 (Barefoot Cruising). For you catamaran lovers out there, the Virgin Island Sailing School also offers ASA 114 (Cruising Catamaran) course add-on. They have different sailboat options to choose from but we were most excited to see that they offer a 2017 Fountaine Pajot Helia 44′ Catamaran that has four cabins. This would be a great sailing vacation for the whole family to learn to sail on a catamaran!

Sailing Virgins school is located in the British Virgin Islands and offers certification for ASA courses 101 (Basic Keelboat Sailing) and 103 (Basic Coastal Cruising). One of the courses that stood out to us was their seven-day Beginner Course located in the U.S. British Virgin Islands. Their flagship monohull sailboat is a three-bedroom Beneteau First 40 that sleeps eight. This sailing school would be perfect for a fun trip with friends who all want to learn sailing.

The Virgin Islands Sailing Academy is located on St. Thomas, U.S. Virgin Islands. They offer various ASA courses as well as a study at home coastal navigation course. They offer their sailing courses on a 39-foot Pearson Sloop with all the convenient comforts. Sailing class sizes are typically 3-4 people which means a more intimate sailing environment for your sailing vacation.

Additional Information

If you need further information regarding sailing vacations and sailing schools, please reach out to the individual companies for their information and package prices. We found that most of their sailing vacation prices were displayed on their websites.

If you have participated in a sailing school in the Caribbean, let us now so that we can add them to our list.

On a side note, at the time that this article was written, the sailing schools mentioned in this post offered ASA certifications. It's always a good idea to reference ASA's website prior to booking a sailing vacation.

Bon Voyage!

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Hello! I'm Tiffany, a creative travel writer, mother to three awesome kids, and Floridian. We like to visit beautiful Florida resorts and beaches, Florida State Parks, and explore destinations by boat. I like to write about our travel adventures and provide tips to other families traveling or relocating to the Sunshine State.


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