Liveaboard Sailing School in the Caribbean

The School of Ocean Sailing offers liveaboard sail training courses. We operate in the Caribbean, in the waters surrounding the United States Virgin Islands. The instructional mission of the School of Ocean Sailing is to teach offshore ocean sailing and ocean navigation in a liveaboard setting.

Your sailing school classroom is a well founded, romantic, beautiful, fast, and very sea kindly sailing vessel. SAMANA, a 52' steel offshore sailing ketch, is 63' LOA, has a 16' beam, draws 7', carries 1800 square feet of sail set between two masts, and displaces 34 tons. Built in 1975 in Holland, SAMANA has circumnavigated the globe and has completed several noteworthy offshore passages.

Captain Larry Wheeler and Letty Wheeler are your sailing school instructors. Both Larry and Letty are professional teachers with more than 25 years of classroom teaching experience and over 25 years of experience in sail training. Larry is a United States Coast Guard Licensed Merchant Marine Officer (USCG). The School of Ocean Sailing is a member of the American Sail Training Association (ASTA).

The School of Ocean Sailing operates winters in the Caribbean Sea surrounding the United States Virgin Islands, and your sailing school class begins in Saint Thomas , USVI. You will be sailing in the Atlantic Ocean and the Caribbean Sea surrounding the United States Virgin Islands (USVI) and the British Virgin Islands (BVI).

The curriculum is a rich blend of technical skill, confidence building, and common sense coupled with a spirit of adventure and romance. Instruction centers on the principal objectives underlying the knowledge of ocean sailing, coastal navigation, or celestial navigation. To this end Larry and Letty have dedicated their sailing school, sailing vessel, equipment, sailing routes, and energy.

The School of Ocean Sailing is able to accommodate beginners just learning to sail a large ocean vessel, to students interested in advanced ocean navigation or celestial navigation.

The School of Ocean Sailing offers seven day liveaboard sail training courses. This means you stay aboard the vessel for the full duration of the course. Your course includes all meals, instruction and materials, towels and bedding, toiletries, such as toothpaste and shampoo. No alcohol or smoking is permitted aboard the sail training vessel. Samana is an alcohol, drug and smoke free environment.

We look forward to having you on board Samana.

What they say / Magazine articles and mentions

Sailing School Review USA Today

USA Today

A Mention in USA Today Travel Tips.
Sailing Courses and Training
in the Caribbean

Sailing School Review Good Old Boat Magazine

Good Old Boat Magazine

An in-depth article written by one of our students and published in
Good Old Boat Magazine
Issue 21

Blue Water Sailing Magazine Article

Blue Water Sailing Magazine

A reference about the School of Ocean Sailing in the July 2007 Issue of
Blue Water Sailing Magazine
Page 71.

The instructional mission of the School of Ocean Sailing is to teach offshore ocean sailing and ocean navigation in a liveaboard setting.

  • Give personalized instruction from professional instructors
  • Teach sailing aboard a large, beautiful and well equipped offshore heavy displacement ketch
  • Teach navigation using modern electronic navigation equipment
  • Teach navigation using non-electronic navigation procedures
  • Offer an ocean sailing experience under real ocean conditions
  • Instill confidence
  • Use high quality sextants and celestial navigation materials
  • Offer a balanced blend of formal instruction and practical experience and relaxation
  • Serve excellent food
  • Anchor or moor in quiet anchorages

The best way to get in contact with us is via Email or fill out the Contact Us Form

  • Mailing Address
    P.O. Box 7359
    Portland, ME 04112
  • +1(207) 321-9249


Choosing a sailing school is a personal decision, based on individual strengths and weaknesses, the type of sailor we wish to be, the time and money we have to spend and the manner in which we learn best. I must give high marks to the School of Ocean Sailing and I recommend them to anyone looking for a sailing school.
Cathy McIntire - S/V Kahlua
The School of Ocean Sailing proved to be just that, and more. As a novice ocean sailor, not only did I learn the fundamentals of sailing on the open sea, but also had a relaxing and enjoyable vacation. Captain Larry and Letty are exceptional people with plenty of patience to answer the many questions put to them by the beginning, as well as the advanced, sailor. Each day there was never a dull moment as we sailed from island to island, learning hands-on, covering the key points of navigation, setting the sails just right our heading. Each evening at port began with an incredible dinner aboard Samana, followed by sightseeing or just relaxing on deck gazing at a star-filled sky. From start to finish it was an excellent experience that I would recommend to anyone with an interest in learning more about ocean sailing.
Maureen Colette - Shrewsbury, MA
A great learning experience. Your emphasis on safety and proper planning reflects your dedication to training students to be contentious sailors. My experiences in the last week have given me the skills and confidence to sail the open seas. The food was not bad either.
Bart Elias - Dayton, OH
I'm at peace with Casco Bay at last! Knowledge always overtakes your fears. I've learned so much about navigating and sailing this past week. I now have the confidence to continue exploring the Maine coast by sail, power, or paddle.
Rob Lemire - Newmarket, NH
How much do you want to learn about real weather sailing, the sunny, windy, foggy and wet? The challenge is up to you. Larry and Letty share all the knowledge and skills you will need to make it happen, plus excellent food.
Penny Geisler - Roanoke, VA
I came expecting to learn a bit about celestial navigation and was amply rewarded. What I didn't expect was what was probably the most rewarding of all -- time spent building memories with new friends. I wouldn't trade the time and new friendships for a ransom of gold.
Kurt Harper - Tustin, CA
Samana is an alcohol, drug and smoke free vessel
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