Barefoot Offshore Sailing School (BOSS)
barefootoffshore.com (784) 456-9526

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.

ASA Sailing Certification Courses Offered

ASA 101, Basic Keelboat Sailing
ASA 101, Basic Keelboat Sailing
Learn to skipper a 20' - 27' sloop-rigged keelboat by day, in light to moderate winds and sea conditions. Learn basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards.
ASA 103, Basic Coastal Cruising
ASA 103, Basic Coastal Cruising
Learn to skipper a sloop-rigged auxiliary powered 25'-35' keelboat by day in moderate winds and sea conditions. Learn cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather, safety and seamanship.
ASA 104, Bareboat Cruising
ASA 104, Bareboat Cruising
Learn how to sail a sloop-rigged, auxiliary powered 30'-45' sailboat during a multi-day cruise upon inland/coastal waters in moderate/heavy winds and sea conditions. Learn about provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring / mooring, docking, emergency operations, weather, and more.
ASA 106, Advanced Coastal Cruising
ASA 106, Advanced Coastal Cruising
Learn to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.
ASA 111, Sailing Review
ASA 111, Sailing Review
Desire to improve or re-familiarize sailing knowledge and skills imparted during previous ASA keelboat certification course(s). Student and Instructor jointly decide on goals prior to the start of the review. Student receives a written, personalized Recommended Plan suggesting steps for continued improvement in knowledge and skills proficiencies after the review is completed. This review may be taken multiple times.
ASA 114, Cruising Catamaran
ASA 114, Cruising Catamaran
Learn to skipper an auxiliary-powered sailing cruising catamaran of approximately 30-45' feet in length during a multi-day liveaboard cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions.

Other Services Offered

  • Women Only Courses
  • Couples Courses
  • Private Courses
  • Weekday Courses
  • Weekend Courses
  • Summer Camps for Kids
  • Vacation Charters

Sailing School Reviews / Testimonials

  • 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. Although it is "..."

    Dave Johnson - ASA 104, Bareboat Cruising

  • 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!

    Witold Wyderko - ASA 106, Advanced Coastal Cruising

  • 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.

    Michael Larcher - ASA 104, Bareboat Cruising

  • Happy, Happy, happy - great teachers, beyond all my expectations, dreams come true!

    Adrian Krey - ASA 114, Cruising Catamaran

  • Had an absolutely great time! Our Instructor made it fun and taught in a way that could be understood by anybody. Very informational, helpful and an all-round great trip - thank you!

    Lynn Gee - ASA 103, Basic Coastal Cruising

Contact Information

Barefoot Offshore Sailing School (BOSS)

Address Blue LagoonKingstownSt Vincent & The Grenadines, West IndiesVCO 100Caribbean
Phone (784) 456-9526
Website barefootoffshore.com
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