Each individual island in the Caribbean is influenced by a different country which collectively gives it a feeling akin to wandering around Europe. From the large Latin nations of Cuba and Puerto Rico to the tiny atoll of French St Barts, there is more culture spread around these islands than you’d expect.

Destinations: BahamasBarbadosCayman IslandsCubaDominican RepublicFrench AntillesHaitiJamaicaLeeward IslandsNetherlands AntillesPuerto RicoTrinidad and TobagoTurks and Caicos IslandsVirgin IslandsWindward Islands

The weather is balmy all year round, allowing a range of landscapes that includes cloud forests and scrubland dotted with cacti. There are also interior mountains to balance the magnificent beaches which ring most islands. Just watch out during the summer hurricane season, as the Caribbean regularly gets pounded by massive storms.

If you want to hike in protected national parks or scuba dive you may want to try the US Virgin Islands or the Cayman Islands. Creole culture abounds in the French Antilles destinations of Guadeloupe, Martinique, and St Martin. If it’s pure luxury and indulgence you’re after, head to Anguilla or St Barts. Both of these celebrity-infested islands offer every creature comfort you can imagine, at great expense.

Jamaica is the home of reggae, Bob Marley and the slums of Kingstown. But even its mean streets are nothing compared to the chaos and danger of Haiti’s Port au Prince. Vacation there at your peril. The Dominican Republic along with Trinidad and Tobago are renowned across the globe for their extravagant carnival parties, and their red light districts.

Try Bermuda if you’re nostalgic for the days of the British colonialism, or Cuba if you want to see one of the world’s longest running social experiments still petering along. Tiny enclaves such as St Kitts, Nevis, St Lucia, Curacao, Barbados, Aruba, and the Grenadines are as sublime as anything you’ll find in the tropics. The scene here revolves around laid back beach time and a good night out dancing and drinking local rum.

Although some islands excel above others, expect to find good cooking, great people and incredible scenery just about anywhere you go in the Caribbean. Its proximity to North America makes it a major winter hangout for Americans and Canadians.

Regions

  • Bahamas: The Bahamas, an archipelago of around 700 islands and cays in the Atlantic Ocean, features flat, low-lying islands with white-sand beaches and clear turquoise waters. The climate is tropical, with warm temperatures year-round. Key tourist sites include Nassau, Paradise Island, and the underwater caves of the Blue Hole in Andros. The Bahamas is known for its luxury resorts, excellent diving spots, and marine activities like swimming with pigs in Exuma.

    Nassau

  • Barbados: Barbados is an eastern Caribbean island with rolling hills, white sandy beaches, and botanical gardens. The climate is tropical, with a wet season from June to November. Key tourist sites include Bridgetown, Bathsheba, and Harrison’s Cave. Barbados is known for its colonial history, rum production, and cricket culture.

  • Cayman Islands: The Cayman Islands, consisting of Grand Cayman, Cayman Brac, and Little Cayman, are known for their coral reefs, clear waters, and beach resorts. The climate is tropical marine, moderated by trade winds. Key tourist sites include Seven Mile Beach, Stingray City, and the Cayman Turtle Centre. The islands are famous for scuba diving, snorkeling, and financial services.

    Cayman BracGrand CaymanLittle Cayman

  • Cuba: Cuba is the largest Caribbean island, known for its rich history, historic cities, and lush landscapes. The climate is tropical, with a wet season from May to October. Key tourist sites include Havana, Varadero, Trinidad, and Viñales Valley. Cuba is known for its colonial architecture, vintage cars, and wonderful music and dance traditions.

    HavanaSantiago de CubaTrinidadVaradero

  • Dominican Republic: The Dominican Republic, occupying the eastern two-thirds of Hispaniola, features diverse landscapes of mountains, rainforests, and beaches. The climate is tropical, with variations depending on altitude. Key tourist sites include Punta Cana, Santo Domingo, and the Samana Peninsula. The country is known for its all-inclusive resorts, historic sites, and natural beauty.

    Santo Domingo

  • French Antilles: The French Antilles, including Martinique and Guadeloupe, are known for their volcanic landscapes, tropical forests, and beautiful beaches. The climate is tropical, with a wet season from June to November. Key tourist sites include Mont Pelée, Les Salines, and Carbet Falls. The French Antilles are known for their blend of French and Caribbean culture, cuisine, and Creole heritage.

    GuadeloupeMartiniqueSaint Barthelemy

  • Haiti: Haiti, sharing the island of Hispaniola with the Dominican Republic, is known for its mountainous terrain, historical sites, and distinct cultural heritage. The climate is tropical, with a wet season from May to October. Key tourist sites include the Citadelle Laferrière, Sans-Souci Palace, and the beaches of Jacmel. Haiti is known for its art, music, and historical significance as the first independent black republic.

  • Jamaica: Jamaica is a mountainous island with stunning beaches, rainforests, and rich musical heritage. The climate is tropical, with a wet season from May to November. Key tourist sites include Negril, Dunn’s River Falls, the Blue Mountains, and Kingston. Jamaica is known for reggae music, jerk cuisine, and all-inclusive resorts.

    Kingston

  • Leeward Islands: The Leeward Islands, part of the Lesser Antilles, are known for their tropical beaches, volcanic landscapes, and unique blend of cultures. The climate is tropical, with a wet season from June to November. Key tourist sites include Saint Martin/Sint Maarten, Antigua, and Saba. The Leeward Islands are known for sailing, snorkeling, and historic sites.

    AnguillaAntigua and BarbudaMontserratSaint Kitts and Nevis

  • Netherlands Antilles: The Netherlands Antilles, now dissolved into Curaçao, Aruba, and Sint Maarten, are known for their white-sand beaches, clear waters, and Dutch colonial architecture. The climate is tropical, with less pronounced wet seasons. Key tourist sites include Willemstad in Curaçao, Eagle Beach in Aruba, and the nightlife of Sint Maarten. The islands are known for diving, duty-free shopping, and a mix of Caribbean and European influences.

    ABC IslandsSabaSint EustatiusSint Maarten

  • Puerto Rico: Puerto Rico, a US territory, features a diverse landscape of mountains, waterfalls, and tropical rainforests. The climate is tropical, with a wet season from April to November. Key tourist sites include Old San Juan, Isla Verde, and El Yunque National Forest. Puerto Rico is known for its historic forts, festivals, and beautiful beaches.

    San Juan

  • Trinidad and Tobago: Trinidad and Tobago consist of two islands with distinct characters: industrial Trinidad and serene Tobago. The climate is tropical, with a dry season from January to May. Key tourist sites include Port of Spain, Caroni Swamp, and Pigeon Point. The islands are known for Carnival, birdwatching, and calypso music.

  • Turks and Caicos Islands: The Turks and Caicos Islands are known for their stunning beaches, clear turquoise waters, and luxury resorts. The climate is tropical, with a relatively dry season from November to April. Key tourist sites include Grace Bay Beach, coral reefs for diving, and the Grand Turk Lighthouse. The islands are known for diving, snorkeling, and upscale tourism.

  • Virgin Islands: The Virgin Islands, comprising the US Virgin Islands and the British Virgin Islands, are known for their beautiful beaches, clear waters, and sailing culture. The climate is tropical, with a wet season from June to November. Key tourist sites include Trunk Bay in St. John, the Baths in Virgin Gorda, and the port of St. Thomas. The Virgin Islands are known for yachting, snorkeling, and historical sites.

    British Virgin IslandsUS Virgin Islands

  • Windward Islands: The Windward Islands, part of the Lesser Antilles, include islands like Saint Lucia, Saint Vincent and the Grenadines, and Grenada, known for their lush landscapes and beautiful beaches. The climate is tropical, with a wet season from June to November. Key tourist sites include the Pitons in Saint Lucia, the Tobago Cays in Saint Vincent and the Grenadines, and Grand Anse Beach in Grenada. The Windward Islands are known for hiking, sailing, and spice production.

    DominicaGrenadaSaint LuciaSaint Vincent and the Grenadines