It’s always the perfect time to visit the Caribbean

Aruba beach with pink flamingos at the beach, flamingo at the beach in Aruba Island Caribbean. A colorful flamingo at beachfront, woman on the beach with flamingos
There's an ideal time to visit the Caribbean, but the consistently tropical temperatures mean there’s lots to do year-round too © Getty Images / iStockphoto

Is there ever a bad time for a Caribbean vacation? Aside from the threat of heavy rains during hurricane season, the region is generally blessed with consistently tropical temperatures, clear yet impossibly blue seas, infinite stretches of white sand, verdant rain forests and flavorful cuisine. 

Weather conditions vary slightly between destinations, but vacationers looking for a respite from the winter months head to the islands during high season, between December and April, when humidity is low and breezes are cool – though the influx of visitors brings higher prices and more crowds. Luckily, the region’s calendar is packed year-round, so there’s always something to do. The low and shoulder seasons are also the perfect time to snag a travel deal. Here’s what to expect throughout the year.

Visit between December and mid-April for peak whale watching

If you’re from an area that typically experiences harsh winters or a cooler climate, the consistently favorable and warm Caribbean weather is particularly appealing between December and April. But plenty of other travelers are also flocking to the islands too, which means less availability on flights and accommodation, higher room rates and airfare and more crowded beaches and attractions.

Even so, high season is the optimal time for whale watching. Dominica is the whale-watching capital of the region and the only country in the world sperm whales call home year-round. French island Guadeloupe harbors 15 species of whales and hosts multiple whale-watching excursions from December to May. 

Key Events: Three Kings Festival, Puerto Rico; Sugar Mas, St Kitts and Nevis; Atlantic Rally for Cruisers, St Lucia

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The best of Caribbean islands

Find the best prices from June to November  

Summer ushers in the Caribbean’s hurricane season, but the increase in rainfall usually yields deals on everything from flights to hotel rooms. Wet weather doesn't dampen the spirit of the region and its resilient people – many islands, such as St Lucia, St Vincent, Barbados and Antigua indulge in the revelry and splendor of carnival (vaval) between June and August.

It’s also turtle-nesting season in Barbados, Bequia, Nevis and Dominica. Decompress and satisfy your sweet tooth with decadent cocoa-infused tours, spa treatments and classes over in St Lucia, where August is designated as Chocolate Heritage Month.

Key Events: Portland Jerk Festival, Jamaica; McLean’s Town Conch Cracking Festival, Bahamas; Pirate Week, Cayman Islands; Tour de Yoles Rondes, Martinique; Anguilla Tranquility Jazz Festival; Spicemas Grenada

Hit the beach from mid-April to June  

Not only will you save money with discounts and deals during the region’s shoulder season, you will also avoid the touristy crowds – the most difficult decision will be which alluring slice of sand to lounge on.

The Bahamas beckons with the silky, pale-pink sands of Harbour Island. Anguilla’s pristine Shoal Bay regularly features on the best beaches list. Antigua and Barbuda has 365 beaches with warm and tranquil waters to choose from. And the Baths in the British Virgin Islands are unmatched in sheer natural beauty. Truthfully, you will find the perfect pocket of powdery sand and pellucid waters on almost any Caribbean island. 

Key Events: Oistins Fish Festival, Barbados; French Surfing Competition, Guadeloupe; Hike Fest, Dominica

January is prime time for fishing in Grenada

Grenada’s azure waters are ideal for deep-sea fishing year-round. But the prime time for a good catch falls in the high season between December and April. The Spice Island Billfish Tournament draws anglers from around the region and beyond for a week of fishing, with local cuisine and music peppered throughout the festivities. The tournament follows international catch-and-release standards, allowing only potentially record-breaking billfish to be brought to the weigh station.

A costumed man in a Carnival parade in front of a giant fish float
The largest — and arguably the best — carnival event of the region is held in Trinidad and Tobago © Getty Images / Photon RM

Trinidad & Tobago host the best Carnival in the region in February 

Carnival is synonymous with the Caribbean, with several islands hosting their own version of the flamboyant festival throughout the year. But the largest — and arguably the best — carnival event of the region is held in Trinidad & Tobago. The pre-Lenten celebration attracts thousands of revelers annually for a nonstop stream of fetes, limbo competitions, pulsating calypso and soca rhythms and an exuberant costumed parade. There's even a term for that post-carnival comedown, or depression, you're guaranteed to feel at the end: it's carnival tabanca, in local parlance. 

The unparalleled Bermuda International Film Festival happens in March 

Since 1997, Bermuda has welcomed cinephiles for the Bermuda International Film Festival (BIFF). The nine-day extravaganza of world cinema is highly respected and features films from the world's leading filmmakers and emerging talent. Attendees also have access to filmmaker Q&As, discussions, masterclasses and parties. In between panels, divers can take in Bermuda’s unparalleled views of the island’s coral and marine life, shipwrecks and underwater caves.

Head to Tobago in April for the Jazz Experience 

Trinidad commands the bulk of the attention, but the smaller half of the twin-island republic, Tobago, is an idyllic escape. The Tobago Jazz Experience is the marquee event, an opportunity for visitors to soak in the easygoing yet intoxicating atmosphere of the island in between performances by world-renowned jazz, R&B, soca, calypso, reggae and Latin artists. 

Looking down on a harbor with boats, framed by greenery and mountains in the distance
One of the top regattas in the world takes place in Antigua, just off the waters of English Harbour © mbrand85 / Shutterstock

Antigua sailing week in May is one of the top regattas in the world

One of the top regattas in the world takes place in Antigua, just off the waters of English Harbour in the Saint Paul parish. Sailors from Russia to South Africa converge on the island in more than 100 yachts, for equal parts competition and socializing during Antigua Sailing Week

The St Kitts music fest in June features the best of Caribbean music

St Kitts is tiny, but the island’s music fest has a strong reputation internationally. Besides the impressive lineup of soca, jazz, R&B, gospel and reggae performances, patrons enjoy grabbing food from the local vendors onsite and settling in on a blanket for picnics on the expansive lawn at the Kim Collins Athletic Stadium in Basseterre. 

Jamaica’s best party, Reggae Sumfest, is in July

Jamaica boasts myriad musical legends, none greater than reggae icon Bob Marley, and the genre is honored at Reggae Sumfest, the largest music festival in Jamaica and the Caribbean. The week-long event kicks off with a beach party, followed by a free street dance, a global sound clash and an all-white party. The final two nights feature live performances from the best reggae and dancehall artists in the world. Past bills have included local superstars Ziggy Marley, Barrington Levy, Vybz Kartel, Spice and Beenie Man and international powerhouses 50 Cent, Rihanna and Kanye West. 

Palm trees framing a white-sand beach with turquoise water on a bright day
Barbados is often quiet, but in the summer it hosts a three-month fete culminating in Kadooment Day in early August © TommL / Getty Images

Kadooment Day on Barbados is August’s premier event

Barbados’ Crop Over tradition originated as a celebration to mark the end of the annual sugarcane harvest. Now it is the island’s premier event, combining music, arts, food and culture. The pièce de résistance of the three-month fete is the colorful, costumed carnival parade known as Kadooment Day in early August. 

Immerse yourself in Aruba’s history during Fiesta di Cunucu in September 

Aruba’s Fiesta di Cunucu is an immersive experience exploring the island’s heritage through its traditional housing. During the exhibition, cunucu homes are furnished with antiquities from the community museum to provide an authentic replication of past living conditions. The program also integrates Aruban music, folkloric dances, handcrafts and a farmers market with fresh local produce. 

Indulge in St Lucia’s best Creole cuisine during Jounen Kwéyòl in October 

St Lucia honors its French and African cultural influences throughout the entire month, but the main event is Jounen Kwéyòl (Creole Day), on the the last Sunday of October. Select communities around the island host locals and visitors alike for musical and cultural performances – and, of course, for creole fare, such as callaloo soup, bouillon, smoked herring, coconut balls, accras (fishcakes) and green figs and saltfish, St Lucia’s national dish. 

Turks & Caicos welcome the best chefs in the world in November

Foodies and oenophiles descend upon Turks & Caicos in early November for the Caribbean Food and Wine Festival. The event brings together top international chefs, gourmet meals and wine tastings, set against the paradisiacal backdrop of the islands' turquoise waters and white sand beaches. 

The Bahamas celebrates Junkanoo in December

Carnival is not relegated to a summer activity. The Bahamas celebrates both Boxing Day (the day after Christmas) and New Years Day with Junkanoo party parades in the capital of Nassau. But the vibrant pre-dawn festival vibe is also woven into celebrations in Bimini, the Exumas, Grand Bahama, Eleuthera and Harbour Island, the Abacos and the rest of the 16 islands.

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