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Top Holidays
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Vintage vibes and
Vintage vibes and

Ultra Luxury Cuba Holidays

Take it back in time on a luxury beach holiday like no other. Cuba is the largest of the Caribbean Islands and the perfect place for relaxation, seclusion, and the chance to immerse yourself into its deep history and diverse culture. With miles of pristine beaches boasting bone-white sands fringed by impeccable cerulean ocean waters, Cuba is certainly one for the bucket list.

Luxury hotel resorts along the coastline are plentiful here, most notably in the ever-popular beach area of Varadero. Each resort is a haven of tranquillity and offers the laid-back atmosphere of the Caribbean but with its own hum of activity, particularly on the beach. Facilities and amenities are abundant and include thrilling water sports, restaurants serving delicious cuisine, and relaxing spas for a spot of indulgence.

Your beach resort hotel may feature everything you need to stay put, but Cuba is begging to be explored. The vibrant capital city, Havana, is the beating heart of Cuba and a hub of historical significance. Havana is renowned for its intoxicating blend of colonial and Art Deco architecture, as well as the distinctive Malecón, a seafront esplanade that envelops the central districts. The city’s plazas, boulevards, cafés, and nightclubs, particularly around the old town, are constantly abuzz with activity. And of course, no visit to Havana is complete without a private city tour in a classic vintage car!

Beyond the capital, Cuba is dotted with colourful colonial towns and stunning regions to explore that embody a more relaxed feel, including the UNESCO World Heritage Sites of Trinidad and Valle de Viñales, as well as the city of Santiago de Cuba for discovering the nation’s revolutionary history.

Never say goodbye to Cuba—just simply wave and say, “see you soon”, because after one visit, you’ll be hooked!
Take it back in time on a luxury beach holiday like no other. Cuba is the largest of the Caribbean Islands and the perfect place for relaxation, seclusion, and the chance to immerse yourself into its deep history and diverse culture. With miles of pristine beaches boasting bone-white sands fringed by impeccable cerulean ocean waters, Cuba is certainly one for the bucket list.

Luxury hotel resorts along the coastline are plentiful here, most notably in the ever-popular beach area of Varadero. Each resort is a haven of tranquillity and offers the laid-back atmosphere of the Caribbean but with its own hum of activity, particularly on the beach. Facilities and amenities are abundant and include thrilling water sports, restaurants serving delicious cuisine, and relaxing spas for a spot of indulgence.

Your beach resort hotel may feature everything you need to stay put, but Cuba is begging to be explored. The vibrant capital city, Havana, is the beating heart of Cuba and a hub of historical significance. Havana is renowned for its intoxicating blend of colonial and Art Deco architecture, as well as the distinctive Malecón, a seafront esplanade that envelops the central districts. The city’s plazas, boulevards, cafés, and nightclubs, particularly around the old town, are constantly abuzz with activity. And of course, no visit to Havana is complete without a private city tour in a classic vintage car!

Beyond the capital, Cuba is dotted with colourful colonial towns and stunning regions to explore that embody a more relaxed feel, including the UNESCO World Heritage Sites of Trinidad and Valle de Viñales, as well as the city of Santiago de Cuba for discovering the nation’s revolutionary history.

Never say goodbye to Cuba—just simply wave and say, “see you soon”, because after one visit, you’ll be hooked!
Take it back in time on a luxury beach holiday like no other. Cuba is the largest of the Caribbean Islands and the perfect place for relaxation, seclusion, and the chance to immerse yourself into its deep history and diverse culture. With miles of pristine beaches boasting bone-white sands fringed by impeccable cerulean ocean waters, Cuba is certainly one for the bucket list.

Luxury hotel resorts along the coastline are plentiful here, most notably in the ever-popular beach area of Varadero. Each resort is a haven of tranquillity and offers the laid-back atmosphere of the Caribbean but with its own hum of activity, particularly on the beach. Facilities and amenities are abundant and include thrilling water sports, restaurants serving delicious cuisine, and relaxing spas for a spot of indulgence.

Your beach resort hotel may feature everything you need to stay put, but Cuba is begging to be explored. The vibrant capital city, Havana, is the beating heart of Cuba and a hub of historical significance. Havana is renowned for its intoxicating blend of colonial and Art Deco architecture, as well as the distinctive Malecón, a seafront esplanade that envelops the central districts. The city’s plazas, boulevards, cafés, and nightclubs, particularly around the old town, are constantly abuzz with activity. And of course, no visit to Havana is complete without a private city tour in a classic vintage car!

Beyond the capital, Cuba is dotted with colourful colonial towns and stunning regions to explore that embody a more relaxed feel, including the UNESCO World Heritage Sites of Trinidad and Valle de Viñales, as well as the city of Santiago de Cuba for discovering the nation’s revolutionary history.

Never say goodbye to Cuba—just simply wave and say, “see you soon”, because after one visit, you’ll be hooked!
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Flawless
Beaches

Cuba’s beaches are tranquil expanses of powder-white sands and clear blue waters, from the iconic and ever-popular beach resort of Varadero to the secluded, bleach-white sands of Playa Paraíso.

Flawless Beaches

Cuba’s beaches are tranquil expanses of powder-white sands and clear blue waters, from the iconic and ever-popular beach resort of Varadero to the secluded, bleach-white sands of Playa Paraíso.

Stunning
Architecture

The streets of Old Havana are a kaleidoscopic mix of colonial and Art Deco architecture in a fusion of styles and cultural influences, creating its one-of-a-kind, and distinctly Cuban, feel.

Stunning Architecture

The streets of Old Havana are a kaleidoscopic mix of colonial and Art Deco architecture in a fusion of styles and cultural influences, creating its one-of-a-kind, and distinctly Cuban, feel.

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Superior
Rum

When in Cuba...! Try a famous mojito, daiquiri, or Cuba libre cocktail—all made with smooth white rum—for a true taste of this gorgeous place.

Superior Rum

When in Cuba...! Try a famous mojito, daiquiri, or Cuba libre cocktail—all made with smooth white rum—for a true taste of this gorgeous place.

Inspired?
Start planning your
next trip today

Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.

Luxury Cuba Hotels

Luxury Cuba Hotels

Gran Hotel Manzana Kempinski La Habana

Havana, Cuba

As Cuba's first luxury hotel, Gran Hotel Manzana Kempinski stands proudly in the heart of Old Havana, surrounded by UNESCO World Heritage sites and the rich tapestry of Cuban history.

As Cuba's first luxury hotel, Gran Hotel Manzana Kempinski stands proudly in the heart of Old Havana, surrounded by UNESCO World Heritage sites and the rich tapestry of Cuban history.

As Cuba's first luxury hotel, Gran Hotel Manzana Kempinski stands proudly in the heart of Old Havana, surrounded by UNESCO World Heritage sites and the rich tapestry of Cuban history.

Paradisus Princesa del Mar Resort & Spa

Varadero , Cuba

Experience an adults-only all-inclusive resort on Varadero's beachfront, featuring select cuisine, extensive activities in a natural setting and exclusive Royal Service with personalised benefits amid Cuba's natural beauty and exceptional service.

Experience an adults-only all-inclusive resort on Varadero's beachfront, featuring select cuisine, extensive activities in a natural setting and exclusive Royal Service with personalised benefits amid Cuba's natural beauty and exceptional service.

Experience an adults-only all-inclusive resort on Varadero's beachfront, featuring select cuisine, extensive activities in a natural setting and exclusive Royal Service with personalised benefits amid Cuba's natural beauty and exceptional service.

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Start Your Journey


Before you book your holiday to Cuba, discover more with these insightful reads and holiday ideas.

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Why Book with Us?

Learn more about our range of services and what makes our team tick

Whether it's a restaurant reservation, a last-minute flight change, or something extra special, we're here to make it happen
Whether it's a restaurant reservation, a last-minute flight change, or something extra special, we're here to make it happen
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10 reasons to book with Winged Boots

You'll soon understand why we're a leading luxury travel specialist

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Winged Boots Interviews: Claire Baker, Luxury Concierge for Winged Boots

From reservations to romantic proposals, see how our dedicated personal experience team can add some extra sparkle to an already incredible travel experience.

Cuba in a nutshell

Varadero is a must-visit hotspot due to its wide expanse of soft, powder-white sands, gentle waves and beautifully warm waters for the perfect swim. Beachfront relaxation is delightful, however there is an array of high-octane motorised water sports available to unleash your inner adrenaline junkie, including banana boats, jet-skiing, and water skiing. Most all-inclusive resorts offer plenty of non-motorised water sports free of charge like kayaking, pedal boats, boogie boarding, and snorkelling for chilled-out fun on the water.

Like much of the Caribbean, Cuba owes its amazing gastronomy to the fusion of indigenous, Spanish, and African traditions. Rice, black beans, cassava, and plantain are essential accompaniments in classic Cuban cuisine and are usually paired with succulent meats. Seafood is also big on the menu here, naturally!

The award-winning La Guarida restaurant is always a wonderful choice for a Cuban fine dining experience. Located in Havana, this iconic ‘paladar’—the name for privately-owned restaurants in people’s homes—offers a gorgeously rustic setting with an innovative menu and an impeccable wine list.

Elsewhere in the city, delve into some classic Latin flavours at El Chanchullero de Tapas. Popular amongst visitors and locals alike, booking ahead is a good idea as this small but lively restaurant can get quite busy. With a rooftop location and a delicious array of flavoursome Cuban favourites like ropa vieja (beef in a tomato sauce with rice), tamales and nachos, this is the perfect place to absorb the vibrancy of the city.

Cuban coffee is a must-try for any visitor. The island boasts perfect bean-growing conditions and as well as being dark, organic, and full of deep flavour, coffee is also ingrained into Cuban culture.

Cuban cigars are considered the finest on the planet and make great souvenirs! So, whether you’re a keen cigar smoker or just a curious onlooker, think about taking a guided tour round one of its factories in Havana or countryside tobacco farms in Valle de Viñales for an interesting cultural experience.

Cuba is awash with a complicated and fascinating history, and there are few better places to find out more than in Santiago de Cuba, the island’s second capital and the heart of the 1950s revolutionary movement. This vibrant city is also abuzz with life and a continual party-like atmosphere. Check out the Cuartel Moncada, one of Cuba’s best museums, to learn about its turbulent past and see intriguing revolutionary paraphernalia.

This vast island is a hub of lush natural splendour. Take off for a few days from your city or beach base and explore the stunning Valle de Viñales—perhaps the most beautiful place in Cuba. Set a little over 100 miles west of Havana, this striking region is characterised by its dramatic limestone bluffs and provides an idyllic spot for horse riding, cycling, and hiking, allowing you to slow down the pace of your trip and become one with nature.
Varadero is a must-visit hotspot due to its wide expanse of soft, powder-white sands, gentle waves and beautifully warm waters for the perfect swim. Beachfront relaxation is delightful, however there is an array of high-octane motorised water sports available to unleash your inner adrenaline junkie, including banana boats, jet-skiing, and water skiing. Most all-inclusive resorts offer plenty of non-motorised water sports free of charge like kayaking, pedal boats, boogie boarding, and snorkelling for chilled-out fun on the water.

Like much of the Caribbean, Cuba owes its amazing gastronomy to the fusion of indigenous, Spanish, and African traditions. Rice, black beans, cassava, and plantain are essential accompaniments in classic Cuban cuisine and are usually paired with succulent meats. Seafood is also big on the menu here, naturally!

The award-winning La Guarida restaurant is always a wonderful choice for a Cuban fine dining experience. Located in Havana, this iconic ‘paladar’—the name for privately-owned restaurants in people’s homes—offers a gorgeously rustic setting with an innovative menu and an impeccable wine list.

Elsewhere in the city, delve into some classic Latin flavours at El Chanchullero de Tapas. Popular amongst visitors and locals alike, booking ahead is a good idea as this small but lively restaurant can get quite busy. With a rooftop location and a delicious array of flavoursome Cuban favourites like ropa vieja (beef in a tomato sauce with rice), tamales and nachos, this is the perfect place to absorb the vibrancy of the city.

Cuban coffee is a must-try for any visitor. The island boasts perfect bean-growing conditions and as well as being dark, organic, and full of deep flavour, coffee is also ingrained into Cuban culture.

Cuban cigars are considered the finest on the planet and make great souvenirs! So, whether you’re a keen cigar smoker or just a curious onlooker, think about taking a guided tour round one of its factories in Havana or countryside tobacco farms in Valle de Viñales for an interesting cultural experience.

Cuba is awash with a complicated and fascinating history, and there are few better places to find out more than in Santiago de Cuba, the island’s second capital and the heart of the 1950s revolutionary movement. This vibrant city is also abuzz with life and a continual party-like atmosphere. Check out the Cuartel Moncada, one of Cuba’s best museums, to learn about its turbulent past and see intriguing revolutionary paraphernalia.

This vast island is a hub of lush natural splendour. Take off for a few days from your city or beach base and explore the stunning Valle de Viñales—perhaps the most beautiful place in Cuba. Set a little over 100 miles west of Havana, this striking region is characterised by its dramatic limestone bluffs and provides an idyllic spot for horse riding, cycling, and hiking, allowing you to slow down the pace of your trip and become one with nature.
Varadero is a must-visit hotspot due to its wide expanse of soft, powder-white sands, gentle waves and beautifully warm waters for the perfect swim. Beachfront relaxation is delightful, however there is an array of high-octane motorised water sports available to unleash your inner adrenaline junkie, including banana boats, jet-skiing, and water skiing. Most all-inclusive resorts offer plenty of non-motorised water sports free of charge like kayaking, pedal boats, boogie boarding, and snorkelling for chilled-out fun on the water.

Like much of the Caribbean, Cuba owes its amazing gastronomy to the fusion of indigenous, Spanish, and African traditions. Rice, black beans, cassava, and plantain are essential accompaniments in classic Cuban cuisine and are usually paired with succulent meats. Seafood is also big on the menu here, naturally!

The award-winning La Guarida restaurant is always a wonderful choice for a Cuban fine dining experience. Located in Havana, this iconic ‘paladar’—the name for privately-owned restaurants in people’s homes—offers a gorgeously rustic setting with an innovative menu and an impeccable wine list.

Elsewhere in the city, delve into some classic Latin flavours at El Chanchullero de Tapas. Popular amongst visitors and locals alike, booking ahead is a good idea as this small but lively restaurant can get quite busy. With a rooftop location and a delicious array of flavoursome Cuban favourites like ropa vieja (beef in a tomato sauce with rice), tamales and nachos, this is the perfect place to absorb the vibrancy of the city.

Cuban coffee is a must-try for any visitor. The island boasts perfect bean-growing conditions and as well as being dark, organic, and full of deep flavour, coffee is also ingrained into Cuban culture.

Cuban cigars are considered the finest on the planet and make great souvenirs! So, whether you’re a keen cigar smoker or just a curious onlooker, think about taking a guided tour round one of its factories in Havana or countryside tobacco farms in Valle de Viñales for an interesting cultural experience.

Cuba is awash with a complicated and fascinating history, and there are few better places to find out more than in Santiago de Cuba, the island’s second capital and the heart of the 1950s revolutionary movement. This vibrant city is also abuzz with life and a continual party-like atmosphere. Check out the Cuartel Moncada, one of Cuba’s best museums, to learn about its turbulent past and see intriguing revolutionary paraphernalia.

This vast island is a hub of lush natural splendour. Take off for a few days from your city or beach base and explore the stunning Valle de Viñales—perhaps the most beautiful place in Cuba. Set a little over 100 miles west of Havana, this striking region is characterised by its dramatic limestone bluffs and provides an idyllic spot for horse riding, cycling, and hiking, allowing you to slow down the pace of your trip and become one with nature.

frequently asked questions

The island promises sunny skies all year round, so there’s no bad time to visit. Cuba’s dry season lasts from November to April and has less frequent rainfall. In December and January, average temperatures dip a little, but it remains warm. The rainy season lasts from May to October, where you can expect short, almost-daily showers and full-blown rainy days at least once a week.

Hurricane season falls towards the back end of the rainy season in June to November, but Cuba is largely unaffected by them.

In terms of tourism, the first peak season runs from late December (Christmas) until March (Easter break), and the second peak is in the height of summer during July and August. The low season extends from early May to late June, when prices decrease as temperatures increase, and from September to October, coinciding with the onset of hurricane season. During this period there are often reduced prices, less-crowded beaches, and the chance to explore museums at your own pace.
Cuba is a safe country to visit and travel around for UK residents. You are required to have medical travel insurance in place before you visit and you must obtain a tourist card, which is usually available to purchase through your airline alongside your ticket price.

For ease and peace of mind if you're planning on exploring beyond your resort hotel, consider hiring a private tour guide who will provide good hands-on knowledge of Cuban geography. These guides are well versed on handling your requests and will ensure that your cash goes to local entrepreneurs and businesses.
Credit and debit cards are not widely accepted in Cuba and the most reliable form of payment is cash. Cash machines are scarce in Cuba so when you spot one, take out enough for a few days to save a bit of hassle.
It’s easy to fly direct to Cuba from London and flights take about 10 hours, with several UK chartered and scheduled airlines flying to and from Havana, Cayo Coco, Varadero, Holguín, Santiago, and more.
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Inspired?
Start planning your
next trip today

Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.