Rob O'Leary

Cuba Travel Expert

With its faded glamor and colorful history, Cuba is a destination that will confound and amaze in equal measure – and that’s exactly why we love it. Blending Latin and Caribbean influences in a heady cocktail of arts, music and gastronomy, a luxury vacation in Cuba will take you from the rum-scented squares of Old Havana’s Vedado to the cigar-rolled plantations of Vinales and on to pretty pastel-hued Trinidad.

Rob O'Leary

Cuba Travel Expert

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Cuba Highlights


After its renowned 1959 revolution, Cuba was mostly closed off from the outside world. In recent years however it has burst back onto the world stage. A luxury vacation in Cuba will immerse you into a sensory world of music, arts and eating, all set against the rum-soaked scenery of its colonial-era architecture and time-capsule streetlife, where antique Cadillacs still throng the roads of Old Havana. When we talk about luxury here, we’re not talking about gold-plated taps. We’re alluding to the on-the-ground access we can provide, which plays out across settings that are undoubtedly glamorous, stylish, and infinitely chic. Our local guides will truly immerse you into Cuba.


With so much to offer with any luxury vacation to Cuba, there’s no replacing an expert tour around its bustling, iconic capital; letting you dive headfirst into its curious cultural life and historical legacies. Havana stands out as one of the most fascinating cultural hubs in this part of the world – filled with historic plazas and laidback eateries. During your Cuban vacation, you can also retrace the steps of Ernest Hemingway – the ‘Old Man’ himself. The famously bullish American author made a home here for many years, which has been celebrated with the endlessly fascinating Hemingway Museum and the house that was his base.


Once you leave the cities behind you, Cuba opens up into a landscape of staggering natural beauty. Particularly true of the East of Cuba, where we send clients on a journey to the Afro-Cuban stronghold of Santiago de Cuba, revolutionary legacies in the jaw-dropping Sierra Maestra Mountains and the hidden coves and fishing villages of the area’s rarely trodden coastline. Our private guides are on hand throughout these luxury Cuban tours to introduce you to hidden-away locales like the waters of the Yara River, where you can ride, hike and explore the surrounding landscapes. Which almost defy description, with their rugged coastlines, wild rivers, palm-covered hills, and secluded lodges.


Cuba’s rollercoaster recent history has been the subject of innumerable books and films. But it’s important not to overlook its enviable offer of scenic hotels, exquisite dining, and cultural events for discerning travelers. The town of Trinidad, located in the midst of the island, has culture and curios in spadefuls, being known as perhaps the most stunning town in Cuba. Drink in its pastel-hued terraces, flanked by luscious mountains and drooping palms, while getting to grips with everything that this UNESCO world heritage city has to offer (not least the smell of freshly cooking food which wafts throughout this vibrant settlement).


The Bay of Pigs may be best known for a failed American military invasion that took place in 1961, but is today an unmissable component in any of our luxury vacations to Cuba. Not only can you learn about this truly tense period of 20th century history, but you can also take in the breathtaking views of the bay – a regular haunt for frolicking dolphins. It’s also one of the best places on the island to snorkel, before kicking back at La Cueva, a private restaurant famed across the country for its mouth-watering food and excellent wine.

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Get under the skin of the country by interacting with local movers and shakers and have the unique chance to visit places that few people get to see with our expert guides who will lead you on a once in a lifetime trip around the island.

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Escape the crowds and embark on an 11-night cultural discovery to eastern Cuba, where you can explore an authentic and sizzling side this fascinating island nation that few others get to see. This is Cuba, just different.

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Cuba Highlights


Nothing is strictly ‘ordinary’ in Cuba. That’s why we love it, and cannot stop ourselves from coming back. Its hotels, for this reason, embody everything that’s unique about the country - from its fascinating tangle of colonial-era architecture to its Afro-Latin cultural roots. This, of course, includes truly glamorous old-world hotels, both in the cities and in the sprawling landscapes and tobacco plantations that surround them. At the same time, the country also has a unique ecosystem of properties that can’t be found anywhere else.


While Cuba has no shortage of luxury hotels, the country also has a quite unique ecosystem of properties that can’t be found anywhere else. ‘Casa Particulares’ are short-rental homestays, most often located in luxurious, sprawling houses centerd right in the heart of the Cuba’s cities. We can arrange for you to stay at only the most palatial, design-conscious Casa Particulares during your luxury vacation in Cuba. Penthouses designed by tasteful architects and designers are at the top of our list, blending modern comfort with a sense of chic, stylish luxury during your Cuban vacation.


As far as more ‘traditional’ hotels go, Cuba offers everything from small boutiques nestled in the heart of Havana - giving you an enviable perspective on local life - to large, glamorous hotels with more than a whiff of 20th century ambience. Architecturally, checking in to these hotels feels like stepping back in time, or into the fictional world of James Bond. Other unmissable options include city penthouses decked out with fixings and fittings that expertly balance 1950s style with chic, modern comforts. Due to the way in which cities and towns such as Havana and Trinidad have grown, such tranquil oases are often only a short walk away from bustling plazas, shaded squares, and incredibly authentic dining. They’re the perfect platform from which to dive into the sensory throng of Cuban culture.


As an island, many parts of Cuba are rarely that far a drive from the sea. This explains the country’s enviable array of luxury beach resorts and sophisticated hotels, many of which have views directly over the warm, welcoming waters of the Atlantic. The hotels and villas that we have access to include an entire, stunning mansion. Its remarkable old-world, colonial architecture is combined with chic boutique rooms and penthouses, offering up that truly Cuban combination of eclectic culture, modern comfort, and cultural ambience that’s rivalled by few other locations. Cuba’s hotels, particularly those which glance toward the ocean beyond, truly define what we mean by a ‘sense of place.’

  • Population Population 11,200,000
  • Capital Capital Havana
  • Language Language Spanish
  • Currency Currency Cuban Peso
  • Time Difference Time Difference GMT-5
  • Expert Tip Expert Tip

    "The city of Havana comes alive at night, and a great way to see the city is by taking a guided bike ride at night stopping off at bars and rumba clubs to soak in the atmosphere"

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