Cuba, The Cayman Islands

Cuba & The Cayman Islands: Culture & The Reef


November To July


From £6,750pp excl. flights
(based on 2 ppl sharing)

How long

8 nights ideal length

Combine the barefoot luxury of the Cayman Islands with Cuba’s cultural buzz on this envy-inducing twin island trip. Over nine days we’ll take you on tour through the art, music and old-world splendour of Havana, before whisking you off to dive, dine and unwind in the island bliss of Cayman. Together, this is the life, colour and indulgence of the Caribbean at its finest.


As soon as you touch down in Havana, we’ll take you to your private penthouse suite in the hip artistic Vedado neighbourhood to settle in with a mojito and cool off in your private plunge pool on your rooftop terrace. Feeling refreshed, you’ll then head out on a guided walk through the faded colonial mansions and Baroque churches of the Old Town, Havana’s most charming enclave.

Now you’ve got your bearings, delve deeper into the rich history and culture of this vibrant city. Hop into your classic car, such as a 1959 Buick, and enjoy cruising through the streets as we take you on a private tour tailored to your artistic tastes. From rumba lessons and a private glimpse of Carlos Acosta’s new troupe of talented dancers in rehearsal, to visiting galleries or artists in their studios, or a Hemingway-inspired fishing trip to Cojímar, the inspiration of ‘The Old Man and the Sea’, and a peep inside the famous author’s home, left as it was in the 1960’s; immerse yourself in Havana’s rich cultural rhythms.

Make this itinerary yours

Each and every Black Tomato trip is tailored exactly to who you are and what you want to do So tell us about yourself and we’ll create something that’s entirely you.

Start Planning

Cuban evenings are our speciality and we have lined up a whole host of treats for you to choose from. Start your evening off by joining the art crowd for drinks at Pam’s House, an extraordinarily beautiful and arty house frequented by in-the-know local artists. Whilst for dinner, it’s your pick of Cuba’s cultural elite. If gastronomy is your thing, opt for a private dinner with Alberto Gonzalez, one of three Cuban chefs to hold a Michelin star and the only one living here at present. Or, if you’re keen to know more about Cuba’s transformation, join top economist Ricardo Torres for dinner at Rio Mar. But maybe you’d rather just have a quiet evening to yourselves? That’s ok too and No Mas, with it’s simple yet elegant food, is the perfect choice. Whichever option you go for, you’re in for a gourmet evening of sampling the eclectic flavours of Cuba’s growing foodie scene.


Still buzzing from your Cuban adventures, it’s time to take things up a notch. Next, we’ll fly you to dreamy Grand Cayman to rediscover the true meaning of the words island paradise—in just an hour, you’ll be surrounded by luminous white-sand beaches and electric blue seas dotted with reefs and shipwrecks. Each of Cayman’s three islands come with the requisite good looks of the Caribbean, but it’s Grand Cayman that is best-versed in luxurious living, with plenty of chic hotels, exceptional dining and pampering experiences. Step into your room at the boutique Kimpton Seafire Resort + Spa to soak up those first rays on Seven Mile Beach with a cocktail.


To start off, hop into your private helicopter to get the measure of Grand Cayman’s beach-strewn coast from above. The water here is so clear that as you dip and glide through blue sky, you’ll be able to easily pick out the shipwrecks you’ll want to explore on your next adventure—diving the wildlife-rich waters.

With over 365 dive sites including shipwrecks, marine parks and reef walls that descend sharply into a deep blue—it’s easy to see how the Cayman have cemented its place as one of the Caribbean’s top diving spots. There’s one for every day of the year. Zip up your wetsuit and get acquainted with the technicolour marine life as your tour this underwater wonderland, seeing everything in full definition through the incredible visibility. It’s a mesmerising antidote to Havana’s bustle.

Prefer to stay above the water? Set sail on your own luxury yacht to Starfish point, where you can drop anchor, enjoy a delicious bespoke lunch, and go jet-skiing, starfish spotting, or just sun yourself on-deck. Or try a night kayak through the maze-like mangroves to the bioluminescent bay, where your paddles make the waters glow a brilliant blue.


For a true island retreat, we can fly you in a Cayman Airways Twin Otter plane to strand yourself on the lesser-visited Cayman Brac. By day, hike the dramatic rugged cliffs (favoured by an array of birdlife) explore the caves and discover isolated beaches and hidden rock pools. By night recline back at your boutique abode in the Le Soleil d’Or, a chic beachside sanctuary that hugs the shore.

The envious quality of life in Cayman is enhanced by the incredible food. And after the potent mojitos and rich cuisine of Cuba, sampling the organic farm-to-table fare of Le Soleil d’Or will feel like a detox to the palette. But this element of wellness extends to activities as well; limber-up with beachside yoga, receive a full body polish at the spa, and replenish with fresh juices every day.

You’ll return home culturally reinvigorated and relaxed, with memories of rhumba and reef dives, artistic encounters and yachting adventures, channelling your inner Hemingway and enjoying life as a luxurious castaway—surely this combination of the Cayman Islands and Cuba is the very best of the Caribbean in microcosm.

“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 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”