A Year of Travel: Here’s A Caribbean Country to Visit for Every Month

by Khaila Gentle

Although we’re just a couple of days into the new year, many travelers are already thinking about their dream getaways for 2025 and beyond. If you’re a fan of all things Caribbean culture, you may have a Caribbean country (or several) on your bucket list. From the leeward islands in the northeast to the mainland nations of Belize and Guyana in the west and south, there is a lot to be seen and experienced in the Caribbean. Not sure where to start? Here’s a Caribbean country to visit for every month of the year.

January – Puerto Rico

Start the year off strong in Old San Juan at The Fiestas de la Calle San Sebastian. This multi-day celebration, Puerto Rico’s largest festival, is the unofficial end to the country’s holiday season. Watch as throngs of people, music, and colors flood the streets. Plus, enjoy plenty of concerts, street parties, and artisan vendors.

February – Trinidad & Tobago

If you’re suffering from a case of carnival tabanca, set your sights on the twin islands of Trinidad & Tobago for February. Home to the mother of all Caribbean carnivals, Trinidad is a must-visit for travelers who love some good old-fashioned bacchanal. Every year, Trinidad Carnival kicks off the pre-lenten season with several days of concerts, parties, and of, course colorful masquerade road marches.

Similar: Upcoming Caribbean Carnival Dates: When and Where to Go in 2024

March – The British Virgin Islands 

It’s one of the Caribbean’s favorite sailing races, and it happens every spring in the British Virgin Islands. In 2025, the BVI Spring Regatta is set to take place from March 31st to April 6th. Head to the sailing capital of the world for three days of exciting racing and plenty of social activities including bar hangouts, art shows, and musical performances.

April – Barbados

There’s lots to do and see in Barbados in April, from caving to rum tours. Plus, the month falls right at the end of the country’s high season, promising good weather and great adventures.  For seafood lovers, look to the annual Oistins Fish Festival for the ultimate April experience. Found on the island’s southern coast, the fishing village of Oistins comes alive every year. Enjoy good music alongside plenty of crowd favorites like Mahi Mahi and Tuna. This year, the festival takes place from April 18th – 21st. It’s set to feature a slew of entertaining events, including the annual Oistins Parade.

May – Cuba 

For four years straight, Cuba has been awarded Best Cultural Destination in the Caribbean by the World Travel Awards, and with good reason. The region’s largest island nation boasts a rich food and music scene and has plenty of architectural wonders, too. While May does bring a few showers, it’s the best time to visit if you’re traveling on a budget. Head to Havana, and enjoy Mayo Teatral. Or,  celebrate love and diversity with the annual Conga Cubana contra la Homofobia y la Transfobia parade.

June – St. Vincent & The Grenadines 

An underrated gem for getting your carnival fix, the island of St. Vincent comes alive with June for Vincy Mas. Set to include grand events like the Miss SVG pageant, the Parade of the Bands, and a Calypso Monarch competition, it’s one of the biggest annual events of the island nation and is sure to make for a memorable summer.

July – Belize

For the foodies who love a good block party, too, Belize in July is a must. The country’s annual lobster fest (which actually features festivals in multiple locations) is one of its most anticipated and well-attended events. Coastal and island communities like San Pedro, Caye Caulker, Placencia, Hopkins, and most recently, even Belize City, come alive in celebration of the Spiny Lobster Season’s opening. Enjoy plenty of lobster dishes and themed events alongside good music and tons of fun activities. If you’re feeling extra ambitious, try to see how many lobster fests you can attend throughout the month.

August – Grenada

Grenada’s Spice Mas is Caribbean culture undiluted and uncommercialized. Taking place every August, this Caribbean carnival is one part bacchanal and one part love letter to the region’s history. The iconic Jab Jab J’Ouvert road marches, complete with revelers covered in oil and donning devil horns, are as memorable as they are culturally significant. Meanwhle, Pretty Mas sees the streets flooded with hundreds of vibrant costumes. Named after the country’s claim to fame as the spice island of the Caribbean, Spice Mas a unique and must-see experience.

September – Curacao 

September falls in the heart of the Atlantic Hurricane Season, which means that many opt out of traveling during this time. But if you’re looking for a memorable off-season vacation with a hurricane-proof itinerary then the ABC islands are your best best. Head to beautiful Curacao which, like its sister islands Aruba and Bonaire, sit just south of the hurricane belt.  Take in the striking colors and architecture of the capital, Willemstad. Plus, get to enjoy a vibrant tapestry of cultures, including Dutch, African, Caribbean, and Portuguese.

October – St. Lucia

Celebrate Creole Heritage in St.Lucia during the month of October. The highlight of the month is Jounen Kwéyòl (Creole Day), which takes place on the last Sunday in October. The entire month, however, is filled with celebrations dedicated to all things Creole Heritage. Enjoy local dishes, traditional music, cultural dances, and more.

November – Guyana

One of the top birding destinations in South America, Guyana comes alive in November. With diverse habitats ranging from savannah grasslands and mangrove forests to coastal wetlands and lush rainforests, this Caribbean nation is a birder’s dream come true. Harpy Eagles, Parakeets, the spectacular Hoatzin and more await. As far as birdwatching is concerned, the best time to visit is after the two rainy seasons. November marks the start of the second rainy season which means the foliage will be lush and roads and trails may still be dry.

December – The Bahamas

A colorful festival that’s perfect for Holiday Season travel, Junkanoo in the Bahamas is a must when it comes to Caribbean experiences. It was brought to the island nation by enslaved Africans who often recreated traditional festivals from their homeland.  A blend of performance, music, and storytelling, it’s a captivating experience and one that shouldn’t be missed.

Featured: Guadeloupe Carnival, 2022. Photo by Audrey Gabon on Unsplash

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