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

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

ASA 101 – Basic Keelboat Sailing

ASA 103 – Basic Coastal Cruising

ASA 104 – Bareboat Cruising

ASA 105 – Coastal Navigation

ASA 106 – Advanced Coastal Cruising

ASA 114 – Cruising Catamaran

  • Where we are

    Located in St Vincent and the Grenadines, our cruising grounds are the Grenadine Islands. Our live-aboard courses start on St Vincent and visit the many Grenadine islands before returning to St Vincent at the end of the trip.

  • How to get here

    Most persons coming from the US, transit through Barbados, St Lucia or Grenada. The main airlines used to get from Barbados to St Vincent are SVG Air or LIAT.

Sailing School
Steven Holli

“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, April 2017

Steven Holli
Robert & Lindsay Hall

“The Instructor rocked!  The course was fantastic.  We had enough time both for fun and learning” – Robert & Lindsay Hall, Catamaran, April 2017

Robert & Lindsay Hall
Michael Depping

“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, April 2017

Michael Depping
Tina Ammon

An excellent and extremely knowledgeable instructor.  He was very patient with the 3 of us throughout the week.  It was a great combination of teaching and vacation” – Brad, Tina & Jessica Ammon, Beneteau 47, July 2017

Tina Ammon