Barefoot Offshore Sailing School (BOSS)
| (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.

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)

American Sailing Certifications Offered

ASA 101, Keelboat Sailing 1
ASA 101, Keelboat Sailing 1
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, Coastal Cruising
ASA 103, 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 108, Offshore Passagemaking
ASA 108, Offshore Passagemaking
Learn to skipper a sailing vessel on extended offshore passages requiring celestial navigation. Knowledge of long-term passage planning, offshore vessel selection, sail repair, offshore first aid, watch-keeping, emergency procedures, abandon ship protocols, safety and seamanship.
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.
ASA 117, Basic Celestial Endorsement
ASA 117, Basic Celestial Endorsement
Learn to apply basic celestial navigation theory and practice to determine latitude and longitude at sea using a sextant and Nautical Almanac.

Other Services Available

  • Women Only Courses
  • Couples Courses
  • Private Courses
  • Weekday Courses
  • Corporate Team Building Courses
  • ASA 'Challenges'
  • Day Sail Charters (public)
  • Vacation Charters
  • Sailboat Cruises
  • Racing Courses
  • Sail Trim Courses
  • Spinnaker Courses

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, Coastal Cruising

Contact Information

Barefoot Offshore Sailing School (BOSS)

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