The Caribbean Travel Guide

Photo by Kirk Thornton/Unsplash

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why you should visit The Caribbean now

The Caribbean archipelago comprises 28 islands blessed with tranquil waters; sugary, white-sand beaches; and lush landscapes. Travelers here will also find fortresses, churches, and sites tied to centuries of Caribbean history. Although the islands share an outstanding natural environment, each features distinct attributes and activities—go horseback riding across the moon-like landscape of Arikok National Park on Aruba or raft an inland river on Dominica or Jamaica. Sports enthusiasts can take in horse races on Barbados and regattas on Anguilla and Martinique, while shoppers will love the retail outlets on larger islands like the Bahamas and Puerto Rico. For uncrowded beaches and fine-dining options, head to the smaller destinations like Anguilla, Nevis, and the British Virgin Islands. Planning the perfect Caribbean vacation is as simple as matching an island to your desires.

What to know before you go to The Caribbean

When's the best time to go to to The Caribbean?

With its reliably warm temperatures and sunny skies, the Caribbean welcomes visitors year-round, though many opt to avoid the region during hurricane season, which runs from June through November and generally peaks in August and September. Invariably, the Caribbean makes for an ideal winter getaway and is most popular with travelers between November and May.

How to get around The Caribbean

The Caribbean is reachable from multiple U.S. cities via American, JetBlue, Delta, Frontier, Southwest, and United airlines. Larger islands, including Aruba, Barbados, Jamaica, Puerto Rico, and the Bahamas, feature public bus systems as well as widely available taxis and app-based car services, while smaller islands offer van-based taxi services. Visitors can often also arrange excursions or private car transportation via resorts, cruise lines, or third-party providers.

Can't Miss things to do in The Caribbean

- On Barbados, the small, seaside village of Holetown boasts an impressive range of international cuisine. Head to First and Second Streets for restaurants serving everything from Caribbean and Indian to Italian, French, and Asian fare. You’ll also find a variety of local bars, where you can catch live bands playing reggae, calypso, soca, and dancehall rhythms.

- August is prime time to visit Anguilla, when boating season coincides with several island holidays. Mingle with locals while watching the daily sailing races from the shore, cheering on the colorful boats as they crisscross the island’s blue waters and stream onto the beaches. Beachfront DJ music and local food vendors add to the lively atmosphere. 

- These three Caribbean locations are worth a deeper dive: Santurce, Puerto Rico, which features an engaging street art scene and the Santurce es Ley summer art festival; Santo Domingo, Dominican Republic, which has one of the Caribbean’s best-preserved colonial districts as well as the oldest street in the Americas; and Carriacou, Grenada, a tiny sister island within the Grenadian archipelago that’s home to top-shelf diving and snorkeling at uncrowded beaches and pristine coral reefs.

Food and Drink to try in The Caribbean

- As befits a collection of islands linked by a clear sea, fresh fish is standard on any Caribbean menu. The specialties vary, from the spiny Anegada lobster native to the British Virgin Islands to the shark sandwiches that are staple fare in Trinidad and Tobago. 

- Beyond seafood, standout dishes include the spicy jerk chicken of Jamaica and the accras de morue (cod fritters) of Martinique, which blend flavors from Caribbean, African, Creole, and European cuisines.

- Rum is the Caribbean’s signature spirit. It originated in Barbados, but is now produced across the region, with nearly every island offering its own brands and versions. Try Mount Gay in Barbados, Brugal in the Dominican Republic, Appleton in Jamaica, or the famed Havana Club in Cuba.

- A tour of one of the many Caribbean rum distilleries open to visitors provides fascinating insight into the beverage’s history and the important place it holds in Caribbean popular and culinary culture. At Habitation Clément distillery on Martinique, you can explore the founding family’s plantation and learn about the production of the island’s distinctive rhum agricole. Also worth visiting is Casa Bacardi in Puerto Rico, where you can chronicle the history of the brand from its roots in Cuba.

Culture in The Caribbean

In the Caribbean, Kalinago, African, and colonial traditions are ubiquitous and influence the region’s many distinctive cultures. Learn more at La Savane des Esclaves on Martinique, where native Gilbert La Rose runs a working farm and museum detailing the island’s transition from slavery to a free, agriculturally based society. And in the Loiza neighborhood outside San Juan, Puerto Rico, you can browse African-inspired artwork at Samuel Lind Studio or sample authentic African fare like mofongo, bacalaitos, and pasteles at the James Beard–recognized El Burén de Lula.  

Local gatherings like the weekly fish fry in Oistins, Barbados, and the Friday night street parties in Gros Ilet, St. Lucia, offer prime opportunities to experience island food, music, and artwork. For more entertainment, head to the open-air beach bars, where you’ll likely hear distinctive Caribbean music.

Local travel tips for The Caribbean

- Contrary to the easygoing, ganja-smoking perception some travelers have of Caribbean society, locals are largely conservative and hold strong religious convictions. While marijuana is decriminalized on several islands, it remains mostly frowned upon throughout the region.

- Local jitneys and vans are among the most reliable forms of transportation across the Caribbean islands. Your hotel or resort can recommend a driver or excursion company that can also craft exclusive local tours. Always negotiate the price prior to the journey.

- Don’t be afraid to approach roadside food shacks, even if some appear a bit ramshackle. They frequently offer delicious local cuisine sold by friendly vendors.

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Updated: 01/07/22

Guide Editor

A veteran travel journalist and photographer, Brian Major (@BMajorTraveling) is the managing editor, Caribbean for