Luxury Vacations in the Caribbean

Pastel-hued villages, cocoa plantations, white sand beaches, tropical gardens, steaming mud baths, and volcanic peaks. Whether you’re creating your own bespoke blend of rum, snorkeling with Southern Stingrays in Mercers Creek Bay, or learning about the magical waters of Los Aquaticos, the Caribbean is a place rich in color and flavor. Think bioluminescent bays, lush carpets of rainforest, vibrant markets, freshly prepared lobster, and champagne picnics under the stars. From learning how to Rumba with local dancers to starfish spotting at the (aptly named) Starfish Point, it strikes the perfect balance between beach relaxation and island exploration.

Peace and tranquility? 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?


Find your experience

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

Looking for inspiration?

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

“Black Tomato are one of the coolest things in the world. Don’t even try and live without them”

“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 vacations”

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