I’ll sail most anywhere in the Caribbean, but most of the trips I put together are for people who have little way to experience sailing. For that reason, The British Virgin Islands (BVIs) are the best as there are many islands, all clustered together with no open ocean sailing required. If you are an experienced sailor and bringing experienced family or friends, other destinations to consider are the rest of the Caribbean, Belize, the Mediterranean, or the Seychelles Islands.