Cayman Islands + Cuba: The Ultimate Twin Trip

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, then it’s 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, to visiting galleries or artists in their studios, or a Hemingway-inspired fishing trip; immerse yourself in Havana’s rich cultural rhythms. Later, dine with Cuba’s cultural elite at an exclusive supper club in a private home in the leafy Vedado neighbourhood and sample the eclectic flavours of its 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.

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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.

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