Your for anytime anywhere anything hijinks.  | | whiskey drinker | GalPal |   Chief Experience Office |  Let’s get lost…


Ready for a unique experience?

Image Alt



$6900 per person

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 a tour through the art, music and old-world splendour of Havana. Then whisking away 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.

We’ll return home culturally reinvigorated and relaxed, with memories of rhumba, reef dives and rum, artistic encounters and yachting adventures. Return from channelling our inner Hemingway + Gellhorn and enjoying life as a luxurious castaway – surely this combination of the Cayman Islands and Cuba is the very best of the Caribbean that can fill a rum glass.





credit: BT

  • Departure
    Your City
  • Departure Time
  • Return Time
    Approximately 8:30 PM.
  • Dress Code
    Island Getaway the way Hemingway + Gellhorn would have wanted it. Clothing for swimming, diving and hot Havana nights.
  • Included
    5 Star Accommodation
    Personal Guide
  • Not Included
    Airport Transfers
    Departure Taxes
    Entry Fees
    Private Jet
    Private Yacht


As soon as we touch down in Havana, we’ll be taken to our private penthouse suite in the hip artistic Vedado neighbourhood to settle in with a mojito and cool off in our private plunge pool on our rooftop terrace. Feeling refreshed, we’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 we’ve got our bearings, we can delve deeper into the rich history and culture of this vibrant city. Hop into our classic car, such as a 1959 Buick, and enjoy cruising through the streets as we take our private tour tailored to our artistic tastes. From rhumba 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; we'll immerse ourselves in Havana’s rich cultural rhythms.
Cuban evenings are my speciality, don't ask, and I've lined up a whole host of treats for us to choose from. Start our 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. For dinner, it’s our pick of Cuba’s cultural elite. If gastronomy is our thing, we 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 we’re keen to know more about Cuba’s transformation, join top economist Ricardo Torres (yay!) for dinner at Rio Mar. But maybe we’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 we go for, we’re in for a gourmet evening of sampling the eclectic flavours of Cuba’s growing foodie scene. And watching me fill my empty leg with Rum.


Still buzzing (or rather buzzed?) from our Cuban adventures, it’s time to take things up a notch! Next, we’ll fly into dreamy Grand Cayman to rediscover the true meaning of the words 'island paradise'. In just about an hour, we’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 the best-versed in luxurious living with plenty of chic hotels, exceptional dining and pampering experiences. Stepping into our room at the boutique Kimpton Seafire Resort + Spa readying to soak up those first rays on Seven Mile Beach with a cocktail.
FROM ABOVE AND BELOW To start off, we hop into our private helicopter to get a grand look of Grand Cayman’s beach-strewn coast from above. The water here is so clear that as we dip and glide through blue sky, we’ll be able to easily pick out the shipwrecks we’ll want to explore on our 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. Challenge accepted! Zip up our wetsuits and get acquainted with the technicolour marine life as we tour this underwater wonderland, seeing everything in full definition through the incredible visibility. It’s a mesmerizing antidote to Havana’s hustle.
Prefer to stay above the water? Let's set sail on our own luxury yacht to Starfish Point, where we can drop anchor, enjoy a delicious bespoke lunch, and go jet-skiing, starfish spotting, or just sun ourselves on-deck. Or try a night kayak through the maze-like mangroves to the bioluminescent bay, where our paddles make the waters glow a brilliant blue. Clothing optional for either.
WILDERNESS AND WELLNESS ON CAYMAN BRAC For a true island retreat, we fly in a Cayman Airways Twin Otter plane to strand ourselves 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 our 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 for 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.
We’ll return home culturally reinvigorated and relaxed, with memories of rhumba, rum and reef dives, artistic encounters and yachting adventures, channelling our inner Hemingway/Gelhorn and enjoying life as a luxurious castaway. Surely this combination of the Cayman Islands and Cuba is the very best of the Caribbean in miniature. Almost enough to fill a glass.


Our Havana hideaway leads to a beach bungalow to our own private beach.


In the blossoming Vedado region of Havana stands Penthouse Ydalgo. This penthouse suite is decked with artistic décor and fine contemporary fixtures completing a unique Cuban balance of 1950s style with chic modernity. Penthouse Ydalgo is surrounded by emerging Cuban artist studios and is a short walk from experiencing Havana’s colonial past amongst the bustling plazas.


Location, Location, Location! When it comes to the Kimpton Seafire Resort + Spa; a fabulous location is what you get. With its artful inside/outside design, this resort is one of the best places to watch the sea catch fire as the sun sets over another dazzling day on Grand Cayman. No matter the time of day, this beautiful resort gives us a true taste of Cayman life albeit luxe. And on one of the Caribbean’s most talked about beaches.


Le Soleil d’Or  lies nestled in a quiet corner of the rustically elegant island of Cayman Brac. Healthy living, relaxation and adventure are central to the philosophy of this hotel. Boasting its own 20-acre organic garden farm, outstanding personal chef, private tennis courts, fitness centre and cooking school, not to mention the extensive list of activities to do around the island and offshore, the bespoke and secluded nature of this hotel will really allow us to make this Caribbean paradise our own.

Tour Review Scores and Score Breakdown

All the things that your need to know in a simple breakdown.

Value for Money

Write a review

error: Content is protected !!