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

“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.”

BobFeb 2018

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

Nic BassonFeb 2018

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

Robert & Lindsay HallApril 2017

“Joel was fabulous a great instructor.”

David BrociousApril 2018

“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 DeppingApril 2017

“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.”

Jan 2018

“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 HartnettFeb 2018

“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 HolliApril 2017

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

“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

“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

“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

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