Caribbean Caribbean Guide Things To Do Essentials Where to Stay Itineraries Getaways All Caribbean Top Caribbean Events for Every Month of the Year By Robert Curley Robert Curley LinkedIn Twitter Robert Curley is a freelance writer and guidebook author specializing in Caribbean Island and Rhode Island travel. TripSavvy's editorial guidelines Updated on 06/26/19 Share Pin Email Caribbean culture is a rich tapestry woven with influences from Africa, Europe, indigenous peoples, and even Asia. Each month in the Caribbean you'll find celebrations of various aspects of local life--from Carnival to regattas, food festivals to jazz concerts--that welcome visitors to experience the warmth and diversity of the islands. Whenever your schedule allows you to venture down to the islands, good times will await. 01 of 12 January Marc Guitard / Getty Images From Junkanoo in the Bahamas to the Three Kings Festival in Puerto Rico, January is the month to chase away the winter chill with a taste of Carnival and a farewell to Christmas. 02 of 12 February Donald Michael Chambers / Getty Images February is the height of Carnival season in the Caribbean, and the pre-Lenten celebration in Trinidad and Tobago is something that everyone should experience at least once. Plus, what's more romantic than a Valentine's Day trip to the islands? 03 of 12 March Bob Curley The post-Carnival season of Lent is a more solemn time in the Caribbean, but that hardly means that March lacks fun and interesting events, festivals, concerts, and more. These include island-flavored Easter and St. Patrick's Day celebrations. 04 of 12 April Roberta Parkin./Redferns Concerts and Easter celebrations typically highlight the April events calendar in the Caribbean, including the annual Tobago Jazz Festival. The start of low-season rates makes travel this month even sweeter. Continue to 5 of 12 below. 05 of 12 May Gospelfest Barbados May is a great month to be in the Caribbean if you're a fan of live music or sailing. This month's annual calendar includes the Grenada Drum Festival, Barbados's Gospelfest, and Foxy's Wooden Boat Regatta in the British Virgin Islands. 06 of 12 June Meg Stewart / Flickr / CC BY-SA 2.0 June's Crop Over festival is Barbados's version of Carnival, while Vincy Mas is celebrated in the Grenadines. The St. Kitts Music Festival combines R&B, hip-hop, calypso, soca, and more. 07 of 12 July Courtesy of Portland Jerk Festival Jamaican ​jerk flavored foods have become popular worldwide, and in July you can get mouthwatering jerk chicken, pork, sausage, and more at the annual Portland Jerk Festival in Jamaica. Antigua celebrates its Carnival in July as well. 08 of 12 August Anguilla Tourist Board Cup Match--Bermuda's national holiday celebrating the game of cricket--highlights the August event calendar in the Caribbean; Sumfest in Anguilla is a celebration of local culture and sailing. Continue to 9 of 12 below. 09 of 12 September Aruba Cas di Cultura September is a relatively quiet month in the Caribbean, but there are still a handful of moderately high-profile events going on, including a pair of famous fishing tournaments in Jamaica. 10 of 12 October Michel Porro / Getty Images There's more going on in the Caribbean in October than hurricane parties. Nevis and St. Lucia play host to a pair of excellent food festivals during this month, while Bermuda brings in top acts for one of the region's best music festivals. If you like sailing, or just want to party with some sailors, don't miss Bonaire's legendary regatta. 11 of 12 November The McGee / Flickr / CC BY-SA 2.0 November has one of the busiest event calendars of the year in the Caribbean, featuring unique happenings like Pirate Week in the Cayman Islands (which includes a festive pirate "invasion"), the Tranquility Jazz Festival in Anguilla, and the Conch Cracking Festival in the Bahamas. 12 of 12 December Bob Curley Christmas and New Year's Eve take on a unique island flavor in the Caribbean, while the stars shine at the annual Bahamas International Film Festival and traditional parang music is celebrated in Grenada in December. Was this page helpful? Thanks for letting us know! Share Pin Email Tell us why! Submit