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.