September - November (Fall)

In the Fall months (September - November), visitors to the Caribbean will enjoy off-season prices, uncrowded resorts and beaches, and generally great weather (although things begin to cool in the northern islands). November is especially a great time for airfare deals.

While hurricane season officially starts in June, it reaches its peak in the months typically associated with fall in North America. While it is generally rare, it is definitely something to be considered with planning a trip this time of year. This is especially true for the Leeward Islands (US Virgin Islands, British Virgin Islands, Anguilla, St. Kitts and Nevis, Antigua, and Guadeloupe), the central Caribbean (Puerto Rico), and the northern Caribbean (the Bahamas and Turks and Caicos). In the southern Caribbean, hurricanes are much less of a threat. While this does not mean a hurricane can’t affect these islands, statistically speaking, the odds are in your favor for avoiding one if you travel to this part of the region.

Events and Festivals

- Belize Independence Day: Celebrations begin on St. George's Caye Day on September 10 and end on September 21, Independence Day. Expect flag-raising ceremonies and street parades.

- Belizee Carnival: The annual Carnival is held in September in Belize to showcase music, theatre, fashion, and dance.

- World Creole Music Festival: Held at the end of October, this is the highlight of sleepy Dominica’s annual cultural calendar with Creole music like cadence-lypso, Kompas, zouk, soukous, bouyon, and even Louisiana zydeco.

- Pirates Week: This annual event in the Cayman Islands celebrates the nation's cultural heritage and pirate legends. Spectators are treated to parades, fireworks displays, street dances, and costume contests.

- The Barbados Food and Rum Festival: This festival is a series of culinary experiences with acclaimed chefs, rum experts, and mixologists. There are food and rum pairing events, plus a beach party at the Hilton Resort Barbados.

- Mojito Fest: Enjoy unlimited mojitos, food samples from local restaurants, and live music at this festival in Puerto Rico.