Caribbean in May: Weather, Crowds & What to Expect

The Bahamas & Turks & Caicos (The Bahamas, Turks & Caicos)

Late spring brings increasing humidity, and May can already feel tropical with temperatures in the high 20s°C. The islands remain mostly dry compared with the Greater Antilles, but hurricane season looms on the horizon - travel insurance and flexible bookings are sensible by late May. Fishing tournaments and scuba trips still run commonly; bring light, breathable clothing plus insect repellent for dusk.

Greater Antilles (Cuba, Jamaica, Hispaniola - Dominican Republic & Haiti, Puerto Rico, Cayman Islands)

May is when humidity rises and afternoon downpours begin to appear more regularly across the Greater Antilles, although many days remain sunny and warm. San Juan and Santo Domingo will see periodic heavy showers; inland mountains get greener and rivers fill. If you’re planning snorkeling or diving trips, expect warm water but occasional surface chop - bring quick‑dry clothing and mosquito repellent for dusk activities.

Leeward Islands (Northern Lesser Antilles: Anguilla, Antigua & Barbuda, St Kitts & Nevis, Montserrat, Guadeloupe and surrounding islets)

Humidity increases in May and short heavier showers start to show up, though many days remain sunny and warm with highs in the high 20s°C. Travelers aiming for quieter beaches will find better prices but should be prepared for more mosquitos at dusk and occasional muddy trails inland. If you plan diving or fishing, check daily sea conditions since squalls can make small‑boat excursions choppy.

Windward Islands & Southern Lesser Antilles (Dominica, Martinique, St Lucia, St Vincent & the Grenadines, Grenada)

May sees an uptick in humidity and more frequent late‑afternoon thunderstorms, particularly inland on Dominica’s mountainous slopes. Coastal areas remain very pleasant for snorkeling and sailing, but rivers and trails start to run faster and can be slippery - use caution on jungle treks. This month can be quieter for tourists, so it’s a good time to find value in eco‑lodges and guided hikes.

ABC Islands & Southern Caribbean Coast (Aruba, Bonaire, Curaçao, Trinidad & Tobago, Venezuelan islands and mainland nearby coast)

May can begin to show slightly more humidity on Trinidad & Tobago as seasonal patterns shift, but Aruba, Bonaire and Curaçao usually remain relatively dry and arid thanks to their southern location. Diving and reef exploration continue to be superb, and shorelines rarely see prolonged rain. Bring lightweight breathable clothes and expect warm nights near the coast.

Western Caribbean & Central American Caribbean Coast (Yucatán Peninsula - Cancun, Cozumel, Tulum; Belize; Bay Islands of Honduras; Caribbean coasts of Guatemala, Nicaragua, Costa Rica, Panama)

May marks the beginning of the wet season’s approach for much of this bloc: afternoon thunderstorms become more frequent in Costa Rica’s Caribbean lowlands and Nicaragua’s coast, while the Yucatán still sees many sunny hours. The Bay Islands and Belize may have variable sea conditions; diving is still good but operators watch forecasts closely. Bring a rain jacket, mosquito repellent and expect greener landscapes.