The Caribbean is a collection of very different sailing grounds. The British Virgin Islands are famous for relatively compact island-hopping, while other areas can involve longer open-water legs, stronger trades, currents or more formal clearance procedures.
Compare the individual regions in the DreamSail database — their character, season, passage rhythm and route highlights — before you choose a yacht.
The northern-hemisphere winter and spring are popular. Tropical-storm and hurricane risk is a major seasonal planning factor and varies across the region.
Weather varies year to year. Use current marine forecasts, local notices and operator briefings for real decisions.
Competence requirements vary by territory and operator. Charter companies often assess sailing history as well as certificates.
Read DreamSail's qualification guide →Example inspiration in the BVI: Tortola → Norman Island → Cooper Island → Virgin Gorda → Jost Van Dyke → Tortola, with Anegada added only when conditions, experience and operator rules make it appropriate.
The skipper remains responsible for safe navigation, conditions, local restrictions and the operator's permitted cruising area.
Tell DreamSail your dates, guest numbers, yacht type and whether you need a skipper.
