• Current Specials: Discounts Available

    Monohull Learn and Cruise (101,103, 104)
    July 3-9
    July 17-23
    July 24-30

    Catamaran Learn and Cruise (101,103,104,114)
    June 26-July 2
    July 3-9
    July 10-16
    July 17-23
    July 24-30

    More Info

  • Upcoming Sailing Adventures

    Intra-Caribbean Advanced and Offshore Course, Nov 20-26 2022, Jan 29-Feb 4 2023

    BOSS High-level Offshore Cruising, Nov 27-Feb 5, 2022, Feb 5-11 2023

    More Info

  • Due to changing SVG protocols, most fully vaccinated charterers and students do not need to quarantine

    No masks required on board. 100% of our instructors are fully vaccinated.

    More Info

  • FULLY OPERATIONAL FOR 2022 and 2023

    BOSS operates throughout the year, including the traditional “hurricane season”. At 13° North, SVG is south of the path of most named storms. In the rare event that your course is disrupted, BOSS will rebook you for missed time on a subsequent course.

  • Barefoot Offshore Sailing School

    BOSS is a family business, 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.

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Barefoot Offshore Caribbean Sailing School

Whether you are an advanced sailor looking to improve your sailing skills or a beginner who has never stepped foot on a yacht before, Barefoot Offshore Sailing School has the perfect courses for you. Become a fully qualified American Sailing Association or Sail Canada skipper and takecommand of your own yacht or a chartered yacht. Barefoot Offshore Sailing School offers you the chance to get the skills, experience and qualification needed to sail anywhere in the world.

Learn to sail in the Caribbean’s most pristine and exciting sailing ground. The Grenadines are a true sailor’s paradise where perfect sailing conditions can be enjoyed year round. All Barefoot Offshore Sailing School instructors are ASA and/or Sail Canada qualified and provide a safe, fun, professional approach to your learning experience.

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

Click here for the course schedule

Click here for Offshore and Advanced Sailing Adventures

sailing school caribbean
Barefoot Offshore Sailing School

Learn to sail in a true sailors paradise!

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!

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!

“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.”

“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

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.  It is the only Sail Canada school outside of Canada.

The company, a subsidiary of Barefoot Yacht Charters, is owned and run by folks who have been sailing and living here for 5 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 ASA Certifications

In addition, BOSS offers the following Sail Canada certifications:

3. Rob’s Response: How do Sail Canada cruising courses differ from ASA?

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Barefoot Offshore Sailing School is one of the few schools in the world, and the only one in the Caribbean, that offers both ASA and Sail Canada certifications. Participants in our courses often ask:  what’s the difference between Sail Canada courses and American Sailing Association (ASA) courses?  Is there an advantage to one system over […]

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5. What is a Barefoot Offshore Sailing School “mentored charter”

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Barefoot Offshore Sailing School offers a “mentored charter”.  This helps graduates of our sailing courses make the transition to sole responsibility as skipper of a chartered boat. What is a mentored charter? In a mentored charter, the charter skipper agrees to shadow one of our sailing course boats during their initial charter.  The BOSS Instructor […]

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6. What is a Barefoot Offshore Sailing School “private course”?

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In addition to our normal scheduled ASA and Sail Canada courses, Barefoot Offshore Sailing School (BOSS) offers the option of a “private course”. What is a private course? In a private course, a guest charters and provisions a vessel from the fleet of our sister company, Barefoot Yacht Charters. There is an additional fee for a […]

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Our Instructors, some of whom have been with us for many years, are not only certified American Sailing Association and Sail Canada 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.

Our Team