1-784-456-9526 bookings@barefootyachts.com Facebook ASA & Sail Canada certified · 20+ years in the Grenadines
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Celebrating 20 years of teaching sailing in the Grenadines!

Welcome to Barefoot Offshore Sailing School!

BOSS offers a full slate of week-long courses offering ASA certifications. Click any item below for full details.

American Sailing Association

ASA courses

Sail Canada

Sail Canada courses

In response to requests from the many Canadians that participate in BOSS courses, in 2018 BOSS became the only registered Sail Canada school outside Canada, and recruited a roster of leading Sail Canada instructors who are all cross-qualified with ASA. Sail Canada courses, which are available November through April, include:

Beyond the standards

BOSS Special Courses

Building on its 20 years of experience and the unique ocean racing qualifications of Philip Barnard, Barefoot’s Managing Director, BOSS has developed some special courses that build on but go beyond the ASA and Sail Canada standards. BOSS Special Courses include:

Student reviews

Testimonials from some of our Barefoot Offshore Sailing Schools

“Mr. Pratley, Thank you for reaching out to me. I would very much agree that I received a great deal of value for my dollar in terms of my experience with Barefoot Charters. My interactions with the staff and instructors were pleasant, and I feel very comfortable recommending Barefoot to my family and friends. I especially am appreciative of my instructor, Rob; he was an outstanding teacher and consistently demonstrated professionalism and competence during our entire course. After spending a week under his tutelage, I feel much more confident in my abilities as a sailor to safely operate a boat. Thank you again for reaching out, and I hope to visit again in the future!”
Skip Hecox · February 2019
“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 · Feb 2018
“If you really wish to learn how to sail, this is hands down, the best place on the planet! We did our courses almost 5 years ago and now enjoy our annual bareboat charter every year in SVG paradise!”
Zeljka Gabrovec · FIVE STARS!
“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”
Steven Holli · Beneteau 463 · April 2017
“Barefoot Offshore Sailing School offers excellent well trained instructors in a hands on sailing setting. The instruction is rigorous with the perfect balance of relaxation and exploration of the wonderful Grenadines. The courses have increased my sailing aptitude and confidence.”
Joe Ziolkowski · Advanced course, April 2022
“I think this course was definitely good value because it was one of the cheapest in the Caribbean. I understand why the boat was almost 20 years old…it kind of had to be for the price you charge. Overall I think it was a good course, and a good location to do it in. Thanks”
Scott Mckenzie · February 2019
“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
“Joel was great, perfect to learn from. His instruction is clear and helpful.”
Nic Basson · Feb 2018
“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.”
Bob · Feb 2018
“The Instructor rocked! The course was fantastic. We had enough time both for fun and learning”
Robert & Lindsay Hall · Catamaran · April 2017
“Joel was fabulous a great instructor.”
David Brocious · April 2018