Live aboard sailing school in the Caribbean

The School of Ocean Sailing offers live aboard 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 live aboard 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 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 live aboard 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

sailing school

  • 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


What they say about us / Magazine articles and reviews

USA Today Article School of Ocean Sailing

A mention about our sailing school in USA Today Travel Tips. Sailing Courses and Training in the Caribbean.


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

Blue Water Sailing Magazine

A reference about the School of Ocean Sailing
in Blue Water Sailing magazine:
July 2007 page 71.


Our Mission

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

  • Personalized instruction from professional teachers
  • 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
  • Instil confidence
  • Use high quality sextants and celestial navigation materials
  • Offer a balanced blend of formal instruction, practical experience and relaxation
  • Serve excellent food
  • Anchor or Moor in quiet anchorages

  • Great course. SAMANA is a beautiful ship. She sails beautifully. Captain Larry & Letty are gracious hosts. The food was gourmet quality. Instruction was very informative and our crewmates were amiable and gregarious. (Otherwise known as a good group) –Sandy Newman - Newtown, PA

  • We couldn't have asked for better hosts!!!!!! While the school was more than we imagined, the most unexpected pleasure was Larry and Letty. We felt like guests in their home rather than tenants in a dorm. We will NEVER forget their warm hospitality. –Brian & Laura Higley - Palm City, FL