Entry documents
Most visitors need only a valid passport for short tourist stays across the six islands; many nationalities are visa-exempt. Cuba is the exception: US travellers must qualify under an OFAC general licence category (such as 'Support for the Cuban People') and buy the Cuban tourist card; check current rules before booking.
Puerto Rico is a US territory: US citizens need no passport, and the dollar is the currency. Barbados, Jamaica, the Bahamas and the Dominican Republic use their own dollars and pesos; US dollars are widely accepted in tourist areas of Jamaica and the Bahamas.
When to go
December to April is the dry season and the peak: the best weather, the highest prices, the fullest beaches. Book Christmas, New Year and Easter well ahead.
May to November is hotter, more humid and cheaper, with brief afternoon showers. Hurricane season runs June to November, peaking August to October: the risk is real but the odds on any given week are low, and travel insurance is essential.
The shoulder months, May-June and November, are the sweet spot: good weather, lower prices, thinner crowds.
December to April is the dry season and the peak: the best weather and the highest prices. May to November is hotter, cheaper and wetter, with hurricane season peaking August to October. May-June and November are the sweet spot.
When are you going?
Pick your travel months above.
General guidance from regional climate patterns, not a forecast. Event dates follow their traditional pattern; confirm exact days before booking.
What to pack
Light clothing, swimwear, reef-safe sunscreen, a rash guard for snorkelling, and mosquito repellent. A light rain jacket for the summer months.
Water shoes help on rocky entries (Bathsheba, parts of the DR north coast). A dry bag for boat days. Formal dress codes are rare outside fine dining; resort evenings are smart-casual.