Caribbean
1950s Havana, reggae beaches in Jamaica, bioluminescent bays in Puerto Rico, and Carnival in Trinidad — the Caribbean rewards solo travelers with colour, music, and rum at every turn.
Showing 35 destinations in Caribbean
Barbados
5 citiesBathsheba
Barbados
The wild east coast — dramatic Atlantic surf crashing over mushroom-shaped boulders, the legendary Soup Bowl surf break, and the most dramatic non-beach scenery in Barbados.
Bridgetown
Barbados
The UNESCO capital of the most sophisticated Caribbean island — the birthplace of rum, Crop Over Festival, stunning colonial chattel houses, and the best flying fish sandwich in the world.
Holetown
Barbados
The first English settlement in Barbados — upscale west coast beaches, world-class restaurants, the platinum coast snorkeling, and where the island's finest rum shops gather.
Oistins
Barbados
The real Barbados — a fishing village fish fry on Friday and Saturday nights where locals and travellers share tables, rum punch flows, and the freshest marlin goes straight from boat to grill.
Speightstown
Barbados
Little Bristol — the most authentic town in Barbados, a quiet north coast fishing village of colonial wooden buildings, the Arlington House Museum, and the best rum shop conversations.
Cuba
5 citiesCienfuegos
Cuba
The Paris of Cuba — a UNESCO-listed city of French neoclassical architecture on a stunning bay, the most elegant promenade in the Caribbean, and excellent seafood.
Havana
Cuba
Frozen in time and utterly alive — 1950s American cars, crumbling colonial Habana Vieja, salsa spilling from every doorway, mojitos at La Bodeguita del Medio, and the most complex city in the Caribbean.
Santiago de Cuba
Cuba
Cuba's second city and revolutionary birthplace — the most African-influenced culture on the island, the birthplace of son music, the Moncada Barracks, and Carnaval.
Trinidad
Cuba
Cuba's best-preserved colonial town — cobblestone streets, pastel colonial houses, the best casa particular scene, and the nightlife at Canchánchara bar that goes until sunrise.
Viñales
Cuba
Cuba's most dramatic landscape — mogote limestone karst mountains rising from tobacco fields, classic farmers on horseback, and the freshest hand-rolled cigars on the island.
Dominican Republic
5 citiesCabarete
Dominican Republic
The kitesurfing capital of the Caribbean — consistent trade winds on a crescent beach, a backpacker party scene, surf schools, and the most energetic town on the north coast.
Jarabacoa
Dominican Republic
The City of Eternal Spring — the Dominican Republic's adventure capital in the cool mountains, with whitewater rafting, paragliding, canyoning, and the beautiful Jimenoa waterfalls.
Las Terrenas
Dominican Republic
The DR's most cosmopolitan beach town — a French and Italian expat community on a palm-lined beach, excellent seafood, and the gateway to Samaná's natural wonders.
Samaná
Dominican Republic
The most unspoiled corner of the DR — humpback whale watching in winter, El Limón waterfall through cacao groves, and the peninsula's empty beaches.
Santo Domingo
Dominican Republic
The oldest European city in the Americas — the Zona Colonial's UNESCO streets where Columbus walked, the first cathedral in the New World, and merengue dancing on every corner.
Haiti
5 citiesCap-Haïtien
Haiti
The second city and colonial jewel — the Citadelle Laferrière (a UNESCO fortress on a mountaintop built after the slave revolution), and the palace of Sans-Souci.
Jacmel
Haiti
The cultural soul of Haiti — a southern port of beautiful 19th-century gingerbread architecture, the best Carnival in the Caribbean, vibrant papier-mâché art tradition, and good beaches.
Labadee
Haiti
A stunning private peninsula on Haiti's north coast — turquoise waters, dramatic mountains, and one of the most beautiful natural settings in the Caribbean.
Pétion-Ville
Haiti
The upscale hillside suburb of Port-au-Prince — Haiti's finest restaurants, the gallery scene of Haitian naive art, and the most functional base for exploring the capital.
Port-au-Prince
Haiti
A city of extraordinary resilience and creativity — the world's most vibrant Vodou culture, Iron Market's riot of colour, the Musée du Panthéon National, and Haitian art that commands international galleries.
Jamaica
5 citiesBlue Mountains
Jamaica
The cool, misty highlands above Kingston — hiking to Jamaica's highest peak, the world's finest single-origin coffee estates, and sweeping views of the whole island.
Kingston
Jamaica
The reggae capital of the world — Bob Marley's house-museum, Trench Town's cultural yard, Devon House patties, Blue Mountains coffee, and the raw authentic Jamaica.
Negril
Jamaica
Seven miles of perfect white sand — the Caribbean's most famous sunset strip, Rick's Café cliff diving, reggae all day, and the most relaxed beach culture in the islands.
Ocho Rios
Jamaica
Dunn's River Falls and the Mystic Mountain zip-line — Jamaica's most visited destination, with cruise ship crowds offset by the incredible natural attractions.
Port Antonio
Jamaica
Jamaica's most beautiful and least touristy corner — the Blue Lagoon, bamboo rafting on the Rio Grande, the Reach Falls, and the lush green hills the celebrities found first.
Puerto Rico
5 citiesEl Yunque
Puerto Rico
The only tropical rainforest in the US National Forest system — bioluminescent bays, coquí frogs everywhere, 240-plus species of trees, and waterfalls worth every muddy step.
Ponce
Puerto Rico
Puerto Rico's southern capital and the Pearl of the South — the finest collection of 19th-century architecture in the Caribbean, the Museo de Arte with 3,000 artworks, and excellent local food.
Rincón
Puerto Rico
Puerto Rico's surf capital — consistent winter swells, a community of international surfers, whale watching in season, and the most laid-back village atmosphere on the island.
San Juan
Puerto Rico
Cobblestone streets and Instagrammable candy-coloured houses in Old San Juan — the blue cobblestones, El Morro fortress at sunset, world-class rum bars, and the best roasted pork in the Caribbean.
Vieques
Puerto Rico
An off-island paradise 8 miles from the mainland — the world's brightest bioluminescent bay at Mosquito Bay, wild horses on empty beaches, and the Caribbean the way it used to be.
Trinidad and Tobago
5 citiesAsa Wright
Trinidad and Tobago
One of the world's great birdwatching lodges — a colonial cocoa estate in the Northern Range cloud forest where 170+ species visit the veranda feeders, including the extraordinary oilbird.
Crown Point
Trinidad and Tobago
Tobago's main town and the island's laid-back heart — the Store Bay Friday fish fry, Pigeon Point's powdery beach, and the starting point for reef diving and Buccoo Reef glass-bottom tours.
Maracas Bay
Trinidad and Tobago
Trinidad's iconic beach — a horseshoe of golden sand backed by jungle hills, and the bake-and-shark beach food that is the most debated culinary institution in the Caribbean.
Port of Spain
Trinidad and Tobago
The Carnival capital of the world — the most elaborate street festival on Earth every February, steel pan music invented here, doubles breakfast, and a food culture as diverse as anywhere.
Speyside
Trinidad and Tobago
The world's best manta ray dive site — Speyside Bay is where Atlantic mantas gather year-round, plus the most pristine coral reefs in the southern Caribbean.