Barefoot Offshore Sailing School (BOSS)

Barefoot 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. BOSS is a subsidiary of Barefoot Yacht Charters, 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.

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 recognized certifications. Learn to sail while exploring the islands.

Categories available:

Ocean crossing opportunities (Trans Atlantic with instructor for ASA 107 and 108)
Multi day offshore sailing opportunities (US to Caribbean with instructor for 106, or 117, 107, 108)
ASA Flotillas (Lead by an instructor and perfect mile builder for a first time charterer (104) fresh out of school)
Singlehanded sailing. (Perfect for sailors who wish to sail singlehanded safely)
Safety At Sea
Mentored charters (shadow an instructor who will act as a mentor while on his learn and cruise course with other students. Perfect mile builder for a first time charterer fresh out of school)
Premium “brand specific” schools (Learn on a specific brand like Seawind or Lagoon)

Certifications

101

Keelboat Sailing 1

Welcome aboard to ASA 101, the gateway to your sailing adventure! This foundational course sets the stage for mastering the art of sailing

102 Keelboat Sailing 2

Step up to the next level with ASA 102: Keelboat 2, your gateway to advanced sailing skills and coastal exploration!

105 Coastal Navigation

ASA 105 Coastal Navigation is essential for anyone ready to move beyond day sailing and take command of extended trips along the coast.

106 Advanced Coastal Cruising

Advanced Coastal Cruising is the ultimate course for sailors looking to sharpen their skills and expand their cruising horizons

INITIATIVES

10% Discount

Veterans Program

At American Sailing we recognize the sacrifices made by the brave men and women who have served or are serving in our country’s armed forces. As a token of our appreciation, and our way of saying thank you, we invite veterans and active military personnel to share our passion for sailing by offering a discount on our ASA 101 Keelboat 1 sailing course.

Learn More

Gallery

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Witold Wyderko

Extremely enjoyable time – well organised, prepared and executed course. An outstanding instructor with experience he easily shares with his students. His friendly and easy-going attitude is greatly beneficial to all taking the course – THANK YOU!

Dave Johnson

Hi Seth, I wanted to take a few minutes to acknowledge both Tony and Nancy for their amazing trip last week. The amount of knowledge, wisdom, and experience they imparted in your 101, 103 and 104 course exceeded all expectations.

Michael Larcher

Nancy was a spectacular Instructor. I felt as though I was constantly learning in a safe and fun environment. She is incredibly knowledgeable and held each student to high standards that ensured a high level of learning.