December - April (Winter)

The weather in the winter months (December - April) is absolutely beautiful. The hundreds of islands throughout the Caribbean are sunny mostly every day with few rain showers, warm to hot temperatures and low humidity during the day - perfect for any vacation!

Keep in mind that this is peak tourist season and crowds flock to the Caribbean. You’ll find this especially the case in the resort-heavy destinations such as Jamaica, the Bahamas, and Dominican Republic, (particularly in Punta Cana). While you can avoid the crowds by strategically picking your Caribbean destination, you’ll have to contend with high-season rates no matter where you go. Anguilla Island, for example, is likely to be less crowded, but it tends one of the more expensive islands in the region year round, despite its comparably low number of annual visitors.

Events and Festivals

- St. Nicholas Day: This day is celebrated on December 5th in the Dutch Caribbean, which comprises of Curacao, Aruba, St Maarten, Bonaire, St. Eustatius, and Saba.

- Junkanoo Festival: A celebratory parade and party across the Bahamas, Junkanoo festivals take place on Boxing Day and New Year's Day. The largest party parades are in Nassau, but you can also experience the energetic carnival atmosphere on Grand Bahama, Eleuthera and Harbour Island, Bimini, the Exumas, and the Abacos.

- New Year's Day: Parades are the order of the day in Key West and St Kitts and Nevis Islands, where the streets are full of revelers long into the evening.

- Bob Marley Day: Jamaica celebrates the life and music of Bob Marley on his birthday (February 6) each year.

- Carnivals: St Kitts celebrates from Christmas until New Year's (mid-December through January 2); Aruba, Curacao, and St Kitts celebrates from Christmas until New Year's (mid-December through January 2) all celebrate the annual tradition throughout January; St. Martin, Jamaica, Curacao, St. Barts, and Dominica are among the islands celebrating Carnival in February.