Overview
The Caribbean sailing season is firmly bounded by hurricane season. Most sailors visit between mid-November and late April — a window that offers the most reliable trade winds, lowest humidity, and most comfortable temperatures.
Peak season (December–April)
Trade winds blow steadily from the northeast at 15–25 knots; skies are blue; temperatures are 27–30°C. Christmas–New Year is the most expensive and crowded period. January through March offers the most reliable winds.
Shoulder season (November, May)
November is excellent — prices drop sharply and anchorages are quiet. May is the reverse: trade winds still reliable with the pre-hurricane heat just arriving.
Hurricane season (June–November)
Most charter companies significantly reduce their fleets. The southern Caribbean — Trinidad, Grenada, Bonaire, Aruba — sits south of the main hurricane track and can be sailed year-round with more confidence.
Best islands by season
The BVI is best December–April. The Grenadines are excellent November–May. Trinidad and Tobago and the ABC Islands are viable year-round.