When you’re ready to plan the actual route, hand off to our companion Caribbean sailing itineraries. Contrary to what many assume, most Caribbean charter destinations do not require a formal license to bareboat — but they absolutely require demonstrated experience. When and where to goThe Caribbean charter season runs strongest December through May (dry, steady trade winds, out of hurricane season). How to Charter FAQDo I need a license to charter a boat in the Caribbean? Compiled by All At Sea for anyone planning their first — or fiftieth — Caribbean charter.