There’s Never a Bad Time for a Caribbean Vacation

Caribbean Flamingos

Is there ever a bad time for a Caribbean vacation?

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The Beautiful Islands of The Caribbean

The area is generally endowed with constantly warm temperatures, clear yet impossibly blue oceans, endless lengths of white sand, verdant rain forests, and gourmet cuisine. The only potential downside to this is the chance of heavy rainfall during hurricane season.

Travellers seeking a break from the winter months generally visit the islands during the high season, between December and April, when humidity is low and breezes are cool, despite weather conditions varying slightly between locations. (However, the increase in tourists does result in greater costs and larger crowds.) Fortunately, there is always something to do because the region’s calendar is full all year round. The best times to book a trip are also during the off-peak and shoulder seasons. Here’s what to expect throughout the year.

Visit between December and mid-April for peak whale watching

Whale Watching

If you’re from a place where the winters are normally harsh or the climate is frigid, the constantly pleasant and warm Caribbean appeals from December to April. However, you’ll discover that many other tourists will also be heading to the islands, resulting in fewer flight and lodging options, higher hotel and airfare prices, and more congested beaches and tourist destinations. 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. The French island of Guadeloupe harbours 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

Find the best prices from June to November 

Caribbean Vacation
Fun in the Sun on your Caribbean Vacation

Although the hurricane season in the Caribbean begins in the summer, the increased rainfall typically results in discounts on everything from hotel rooms to flights. The robust inhabitants of the region and the wet climate are unfazed. Between June and August, numerous islands, including St. Lucia, St. Vincent, Barbados, and Antigua, partake in the merriment and splendour of carnival (vaval). It’s also the turtle-nesting season in Barbados, Bequia, Nevis and Dominica. In St Lucia, you can both decompress and satisfy your sweet tooth with decadent cocoa-infused tours, spa treatments and classes, 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 

During the off-peak season in the area, you may take advantage of discounts and bargains while avoiding the tourist crowds. The hardest decision you’ll have to make is which seductive sandbar to lie on.

Couple on the Sand

The smooth, light-pink sands of Harbour Island in the Bahamas beckon. Shoal Bay, on the island of Anguilla, frequently appears on lists of the best beaches. You can choose among 365 beaches in Antigua and Barbuda, all of which feature calm, warm waters. In terms of pure natural beauty, the Baths in the British Virgin Islands are unrivalled. Practically any Caribbean island will have the ideal patch of fine sand and clear water.

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

January is prime time for fishing in Grenada

Deep Sea Fishing

Grenada’s crystal-clear waters are perfect for deep-sea fishing all year long, but the best chance of landing a big catch is during the high season, which lasts from December to April. For a week of fishing, the Spice Island Billfish Tournament attracts anglers from the area and beyond. The celebrations also feature local food and music. Only possibly world-record-breaking billfish are permitted to be transported to the weigh station because the competition adheres to international catch-and-release guidelines.

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


With various islands hosting their versions of the colourful event all year long, the Caribbean is well recognized throughout the world for its dedication to carnival celebrations. However, Trinidad & Tobago hosts the biggest and, probably, best carnival celebration in the entire area. Each year, thousands of partygoers go to the pre-Lenten celebration for its constant schedule of fetes, limbo contests, throbbing calypso and soca beats, and joyful costumed parade. Even a word exists to describe the inevitable depression or comedown after a carnival: “carnival tabanca.” Expect a severe impact.

The unparalleled Bermuda International Film Festival happens in March


Bermuda has hosted movie buffs for the Bermuda International Film Festival since 1997. (BIFF). The prestigious nine-day feast of international cinema showcases works by both established and up-and-coming directors. Participants can also participate in debates, master sessions, parties, and Q&As with filmmakers. Divers can enjoy Bermuda’s unmatched vistas of coral, marine life, shipwrecks, and underwater caverns between panels.

Head to Tobago in April for the Jazz Experience

Although Trinidad receives the most attention, Tobago, the smaller of the twin-island republic, offers a tranquil retreat. In between performances by renowned jazz, R&B, soca, calypso, reggae, and Latin musicians, the Tobago Jazz Experience offers guests a chance to take in the island’s laid-back yet seductive ambiance.

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 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 may be tiny, yet the island’s music festival has a mighty international reputation. Besides the impressive lineup of soca, jazz, R&B, gospel and reggae performances, patrons can enjoy grabbing food from the local vendors onsite before 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, takes place in July

One of the greatest musical superstars from Jamaica is the father of reggae, Bob Marley. Reggae Sumfest, the biggest music event in Jamaica and the entire Caribbean, honours his genre. A beach party marks the beginning of the week-long celebration, which is then followed by a free street dance, a global sound clash, and an all-white party. The world’s top reggae and dancehall musicians play live on the final two evenings. Ziggy Marley, Barrington Levy, Vybz Kartel, Spice, and Beenie Man, as well as worldwide powerhouses 50 Cent, Rihanna, and others, have appeared in previous lineups.

Kadooment Day on Barbados is August’s premier event

Grand Kadooment
Grand Kadooment

Originally, the yearly sugarcane harvest’s conclusion was celebrated as part of the Barbados custom known as Crop Over. It now serves as the island’s premier celebration of music, the arts, cuisine, and culture. The highlight of the three-month celebration is the Kadooment Day procession, a vibrant, costumed carnival that happens in the first few days of August.Immerse yourself in Aruba’s history during Fiesta di Cunucu in September

The Fiesta di Cunucu in Aruba is a comprehensive event that explores the island’s history through its traditional architecture. To accurately recreate previous living conditions, cunucu dwellings are furnished with artifacts from the neighbourhood museum during the display. The programme also incorporates folkloric dances, handicrafts, a farmer’s market with local goods, and Aruban music and dance.

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

Jounen Kwéyl (Creole Day), which is celebrated on the last Sunday of the month, is the biggest event as St. Lucia celebrates its French and African cultural influences during October. A few towns on the island organize musical and cultural events for both locals and tourists, and they also serve up lots of Creole food including callaloo soup, bouillon, smoked herring, coconut balls, accras (fishcakes), and the national meal of green figs and saltfish from St. Lucia.

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

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Food and Wine Festival

Foodies and wine lovers descend upon Turks & Caicos in early November for the Caribbean Food and Wine Festival. This event sees top international chefs dishing up 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 just a summer activity. The Bahamas celebrates both Boxing Day (the day after Christmas) and New Year’s 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 all of the archipelago nation’s 16 islands.

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