Barefoot Offshore Sailing School

Sailing SchoolBarefoot Offshore Sailing School (B.O.S.S.)  is the longest-established (more than 20 years) and most active American Sailing Association (ASA) sailing school in the south-eastern Caribbean.

We run the courses, both catamaran and monohull, every week of the year, in one of the most beautiful sailing grounds in the world – St Vincent & The Grenadines.

Our courses are totally hands-on, live-aboard – and are great not only for novices wanting to learn to sail, but also for experienced sailors looking for formal, internationally recognised certifications.

Learn to sail while exploring the islands – click here for additional details

Barefoot Offshore Sailing School

“The value of the course and learning was amazing and far better quality than expected. Finn’s experience and way of sharing made the course what it was.”


“Joel was great, perfect to learn from. His instruction is clear and helpful.”

Nic Basson

“Joel was fabulous a great instructor.”

David Brocious

“Finn was an astute captain.  He fostered community among the students and taught real world sailing skills in addition to the ASA course work. Friendly, competent and great art teaching. Lucky to have learned from him.”

“Finn was absolutely fantastic. He balanced training for our skill set and brought together 5 crew/strangers and was able to train us all for our very specific needs and skill sets. Heals left us with a need to do more. I have had many training classes, Finn was by far the best trainer I have ever had.”

F Hartnett

“I would like to commend you for running an excellent school with top-notch instructor Richie Britton.  Jeannie and I have different learning styles and Richie was perfect at working through both styles.  He made a tremendous impact to our learning experiences” – Beneteau 463,

Steven Holli

“Fabulous week – great fun on the sea, discovering islands, whilst learning to sail with great company!  Highly recommended!  Many thanks to the team!” – Michael Depping, Monohull

Michael Depping

“The Instructor rocked!  The course was fantastic.  We had enough time both for fun and learning” – Robert & Lindsay Hall, Catamaran, 

Robert & Lindsay Hall

About Us

BAREFOOT OFFSHORE SAILING SCHOOL is the only American Sailing Association (ASA) sailing school in St Vincent & The Grenadines, and is the longest-established (more than 20 years) and most active ASA school in the south-eastern Caribbean.

The company, a subsidiary of Barefoot Yacht Charters, is owned and run by folks who have been sailing and living here for more than 3 generations, and this gives us the unusual advantages of insight and local knowledge that most charter companies, no matter how experienced, simply cannot offer.

Our sailing school offers the following levels of certification

How to Get Here

St Vincent’s new international airport opened in February 2017. We are up-dating this section regularly to let you know which airlines will be flying here.

Air Canada Rouge will recommence bi-weekly non-stop scheduled Autumn/Winter service from Pearson International, Toronto to St. Vincent on October 25th, until April 28, 2018,

  • Thursdays starting October 25
  • Sundays staring Dec 16

The flights will recommence just in time for the 39th annual Independence Day in St. Vincent (October 27).

This is the second year the airline has offered direct flights after the opening of the Argyle International Airport in February 2017.

Two other airlines, American Airlines and Caribbean Airlines are also commencing direct Non-stop flights to Saint Vincent;

  • American Airlines – Starting Dec. 22, Saturdays from Miami
  • Caribbean Airlines – Weekly from New York’s, JFK

Our Instructors, some of whom have been with us for many years, are not only certified American Sailing Association Instructors,  but also people who know the islands intimately and are able to get along with folks of all ages and from all walks of life.