Luxury Caribbean Holidays

Tailor-Made Travel in the Caribbean

Pastel-hued villages, cocoa plantations, tropical gardens, and volcanic peaks. Whether you’re creating your own blend of rum, snorkelling with stingrays in Mercers Creek Bay, or learning about the magical waters of Los Aquaticos, the Caribbean is a place rich in colour and flavour. Think bioluminescent bays, lush rainforests, freshly prepared lobster, and champagne picnics under the stars. From dancing Rumba with locals to starfish spotting at the aptly named Starfish Point, it’s the perfect balance between beach relaxation and island exploration.

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Peace and tranquillity? Or thrills and adventure? Whatever your preference, we’ll find the pace that best suits you. From surfing at the Soup Bowl to visiting the local jazz clubs in Havana. From a helicopter tour over the active Montserrat Volcano to a Rastafarian cooking class in the rainforest. Swim among coral reefs with native Hawksbill turtles. Or simply watch them hatch at Jumby Bay.

Unsure about the best time to visit the Caribbean? Just ask our Travel Experts. From horseback riding among the Sierra Maestra mountains to kitesurfing along the coast of Bathsheba – they really know their stuff. They’ll help you uncover shipwrecks, secret medicinal gardens, and the best beaches in the Caribbean – because they’ve been themselves. Even an underwater sea sculpture park. From beachside yoga to exotic bird spotting. Ready to dive into island life?

Countries

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Explore our inspiring experiences in Caribbean based on when you want to travel and how you want to feel.

Explore our top Caribbean trips

Inspiration to get under the skin of Caribbean

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“Many companies brag about offering once-in-a-lifetime experiences. But with Black Tomato it’s not hyperbole”

“Black Tomato is a super innovative company where the sky is the limit for their clients”

“Black Tomato prides itself on meeting customers every minor need or desires”

“Black Tomato is the choice provider of mind-expanding holidays”

“Black Tomato has made it a mission to keep the world of travel fresh, responsible, and exciting”

“Tailor-made travel experiences that truly get under the skin of a country and its people”

“Black Tomato is a leading luxury travel company that provides innovative and inspiring experiences”