• Barefoot Yacht Charters and BOSS

    Owned and run by yachtsmen, one of whom is a former America’s Cup sailor whose family has lived here in St Vincent & The Grenadines for many generations.

    Learn More

  • Sailing Schools Available!

    ASA 114 Feb 24 – Mar 2
    ASA 106 April 14

    Booking Enquiry

  • Jim Garvin -

    I have been a student here several times. Got certified the first trip, and returned a couple of more times to learn more. So glad I started this journey. Couple of months ago I bought my own sailboat, moved aboard, and am looking forward to retiring in 2 years when I will head down to St Vincent and the Grenadines. BOSS sailing school literally took me from not knowing how to sail, to my retirement dream. Thank you to everyone at BOSS

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LAST MINUTE SPECIAL!! 20% DISCOUNT

ASA 114 Feb 24 – Mar 2

BOOK NOW

Barefoot Offshore Caribbean 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 Caribbean islands – click here for additional details

sailing school caribbean

Boss Last Minute Discount Club

Sign up to join the Boss Last Minute Discount Club and be the FIRST to be alerted to last minute school discounts.

6 Weeks 10% discount save up to $270
4 Weeks 15% discount, save up to $405
2 weeks 30% discount, save up to $810

If you really wish to learn how to sail, this is hands down, the best place on the planet! We did out courses almost 5 years ago and now enjoy our annual bareboat charter every year in SVG paradise!

Zeljka GabrovecFIVE STARS

Excellent sailing school. I completed ASA 101 to 104 with my significant other in April 2017. Fantastic instruction, excellent hands on experience, highly recommend this school. I have the bug now! I want to go sailing every day!

Steve HolliFIVE STARS

“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

“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

About Us

BAREFOOT OFFSHORE CARIBBEAN 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.

Check out Our Team