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You are browsing the UK site. Visit our US site.
You are browsing the US site. Visit our UK site.
You are browsing the US site. Visit our Rest of World site.
You are browsing the UK site. Visit our US site.
You are browsing the US site. Visit our UK site.
You are browsing the US site. Visit our Rest of World site.
Family Holidays
Our team is full of family travellers, meaning we know what it takes to make sure everyone enjoys the experience just as much as each other.
Couples Holidays
Our couple itineraries are paced perfectly for you to enjoy the very best a country has to offer whilst making sure you enjoy the quality time together you’re after.
Group Holidays
No matter what the size or the occasion, we’re well versed in taking larger groups of people away for those special adventures.
Honeymoons
We’ve been crafting dream itineraries for newly married couples for years. Learn more about the ins and outs of our honeymoon service here.
Multi Generational Trips
From very small to very big. Families come in all shapes and sizes, and our multi-generational holidays are perfectly designed to tick the boxes for the whole family.
Anniversary Trips
Whether you’re celebrating as a couple, or across multiple generations, our anniversary trips are crafted around the milestone – and the people sharing it.
Travel With Teens
This is a list of the very best places to travel with teenagers – one that’s crammed with bragging rights (for them) and bonding moments (for you).
Grown Up Family Holidays
As your children become adults, your family trips are also due to change and grow. These are our favourite trips for you and your grown up family.
Solo Holidays
Our travel experts have experienced the thrills and challenges of solo travel, all with the aim of producing some of our most immersive and exciting itineraries.
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Safari Holidays
With a team of experts that have worked as conservationists and wildlife photographers, we have the expertise to make your safari dreams come true.
Remote Destinations
We’ve chosen these experiences, destinations and adventures to bring you closer to the great outdoors. This is your ticket to our wonderful world.
Unusual Holidays
The world may be conquered, but enough secrets remain to keep us up all night, dreaming of ways to whisk you off to the most unique corners of the globe. Where first?
Adventure Holidays
Hike across mountain ridgelines, scramble across glaciers and kayak down rivers – these trips are designed to immerse you in vast wildernesses and ancient cultures.
Beach Holidays
Porcelain shores, perfect seas and swaying palms; the allure of a beach break is hard to ignore. Which is why we handpick the best beachfront boltholes to offer you…
Food Holidays
Food and travel have long gone hand in hand, and we have put together some mouth-watering trips that capture the palate, of countries across the world. Bon appétit.
Slow Travel
As the world becomes busier, slow travel has never felt so fitting. Whether it’s meeting fishermen in Maine or learning the Dukha-way in Mongolia, take time to connect.
Eclipse Holidays
Eclipse travel celebrates our place in the wider cosmos. Let us take you to wherever in the world the eclipse is at its most arresting, and we’ll do it in style.
Proposal Service
Found the one and want to propose in style? The moment will be a memory forever and we’re here to help you make sure it’s the most perfect moment for you and your loved one.
Train Travel
“It’s not the destination, it’s the journey.” We’ve all heard this, haven’t we? And with these captivating luxury train journeys, we’ll show you the joy to be found travelling across the world by rail.
The Pursuit of Feeling
From impassioned and emotive journeys, to podcasts and our Feelings Engine, you’ll find something to move you and something to soothe you. We want to fire your heart and provide food for your soul.
Set Jetting
Swapping salubrious saloons and questionable lodgings for sumptuous hotels and eye-opening experiences, each of our show-stopping journeys will take you behind scenes of some of TV’s most awe-inspiring locations.
See You in the Moment
You need only bring yourselves – your people, your histories. We’ll provide the moment itself. The anticipation, the togetherness, the memory. This is something to savour. This is something to remember.
Field Trip
Education begins in the classroom, but it’s IRL that younger generations put their lessons to the test. Field Trip is a curriculum of educational encounters around the world.
Take me on a Story
A series of family experiences celebrating the transformative power of the books we loved when we were young, and the stories our children have come to adore.
Get Lost
Designed as a once-in-a-lifetime challenge, train with elite survival experts before traversing a polar, jungle, coastal, mountain or desert region in your mission back to civilisation.
Blink
The ultimate luxury camping retreat. From the Sahara desert to the Andean Mountains, with Blink anywhere you can envisage it, we will create it.
Bring it Back
Bring It Back will embed you in an entirely different way of thinking, and of learning about a culture directly from its experts on the ground. You may be surprised by what you discover.
The Great American View
This series of breathtaking journeys culminate in some of America’s most legendary sights. They are the places you’ve always sought out, and now it’s your time to find them.
James Bond
We are proud to have been selected as the official travel partner to curate James Bond inspired trips.
Agatha Christie
We’ve been hand-picked by Agatha Christie Limited to help bring Agatha’s world-famous Grand Tour to life through a series of episodic trips across Africa, Australasia and North America, and a unique prelude in London.
Tasting Notes
Eating at a Michelin – starred restaurant is one thing. But now you can learn about the country through the lens of some of the most critically acclaimed chefs in the world, by travelling with them on the ultimately culinary experience
Take the Open Road with Auberge
With the iconic hotel brand Auberge Resorts, we’ve created a new series of tailormade, luxurious road trip itineraries. Emblems of America’s most iconic landscapes, regions, and people.
Remarkable Drives of Discovery with Auberge
Following on from the much lauded ‘Take the Open Road’ series, here’s five brand-new bespoke, multi-destination trips created with our friends at Auberge Resorts Collection. Delve deeper than ever before.
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Explore our inspiring experiences based on when you want to travel and how you want to feel.
Pastel-hued villages, rum-scented squares and cigar-rolled plantations. Cuba is a favourite on our list.
After its renowned 1959 revolution, Cuba was mostly closed off from the outside world. In recent years, this colourful country has climbed back on to the world stage, drawing attention and welcoming visitors to explore its hidden treasures. Blending Latin and Caribbean influences, Cuba’s sensory world of art, music and gastronomy is mesmerising. Take a step into the past as colonial-era architecture sets the scene, Cadillacs roam the roads and jazz music fills the streets. Looking to experience Cuba’s artistic culture or explore the famed sugar plantations? On a luxury trip to Cuba with us, you’ll see that and much more.
As ever, if you can’t see it here then we can still plan it for you.
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 holiday 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 or all-inclusive resorts. 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 the best that Cuba has to offer.
With so much to offer with any luxury holiday 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 holiday, 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 holidays to introduce you to hidden-away locales like the waters of the Yara River, where you can ride, hike and explore the surrounding landscapes. They 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 and resorts, exquisite dining, and cultural events for discerning travellers. 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. Head out on an excursion to 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 holidays 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. Relax on the white sand beach before kicking back at La Cueva, a private restaurant famed across the country for its mouth-watering food and excellent wine.
Havana
Listen to the sound of jazz as it ricochets off the colourful walls.
Stylish and chic, Havana is one of the most fascinating cultural hubs in this part of the world. Curious minds will fall in love with the historic plazas, laidback eateries and art deco architecture. Our expert guides will truly immerse you into a Cuban lifestyle as you ride in an antique Cadillac, get a private lesson on cigar making and dance the night away in an exclusive salsa lesson.
Trinidad
Discover carpets of rainforest and intrigue on this island.
Holding the title of the most beautiful town in Cuba, the pastel-hued, colonial town of Trinidad is found in the province of Santi Spíritus. Surrounded by luscious mountains and towering palms, Trinidad has a lot to offer; from the entrancing smell of freshly cooked meals to the quaint cobbled streets that line the town. We’ll take you on a history tour of the sugar plantations or on a snorkelling excursion in La Boca. Doesn’t that sound perfect for your next holiday?
Viñales
Experience a slow and relaxed way of life in Cuba’s scenic backyard.
Once you spy a cigar-chewing guajiro ploughing through a rust-coloured tobacco field, you’ll know you’ve reached the tranquil farming town of Viñales. Opt to bed down in a luxury yet traditional homestay, where the locals will guide you in embracing Cuba’s calming countryside lifestyle. Dive into the best of Cuba’s natural world by horse-riding through the UNESCO World Heritage Site of Valle de Viñales or trekking to Los Aquaticos – the Water People – to learn about the magical healing waters.
Gran Hotel Manzana Kempinski La Habana
La Reserva, Havana
Melia Buenavista
The best time to visit Cuba is November to April — the dry season, when humidity drops, temperatures are comfortable, and the island is at its most accessible and atmospheric. December and January are particularly good for Havana, when the city is alive with cultural events and the light through the colonial plazas is exceptional. The summer months bring heat and the possibility of tropical storms, though eastern Cuba and the tobacco valleys of Viñales can absorb a degree of warm weather well. Black Tomato plans Cuba trips year-round, building the itinerary around the season.
Cuba is not a beach resort destination in any conventional sense — and that is precisely what makes it interesting. The private access Black Tomato arranges operates on a different level entirely: a private concert in the home of Havana’s most celebrated rumba musicians, an evening with Alberto Gonzalez (one of three Cuban chefs ever awarded a Michelin star, and the only one based in Cuba), a behind-the-scenes tour of artist studios with someone who knows the city’s creative scene personally. The architecture, the music, the gastronomy, the history — all of it is experienced through people rather than through crowds or commentary. That distinction is the difference between arriving in Cuba and actually understanding it.
Americans can travel to Cuba under specific OFAC licence categories — the most commonly used for private travel is the ‘Support for the Cuban People’ category, which requires meaningful engagement with Cuban private sector businesses, cultural figures, and local community rather than state-run enterprises. Black Tomato designs all US Cuba itineraries to meet these requirements naturally: private guesthouses, independent restaurants, artists in their own studios, local guides who run their own operations. We provide full guidance on documentation and compliance as part of the planning process, and our itineraries are built to satisfy the regulations through the quality of the experience rather than as a compliance exercise.
Havana is the natural starting point, but Cuba rewards those who go further. Viñales, two hours west, is the heart of Cuba’s tobacco-growing country — a valley of extraordinary beauty where the pace of life remains genuinely unhurried and where visiting a working plantation with an expert local guide is a fundamentally different experience from any museum. Trinidad, on the south coast, is arguably the most beautiful town in Cuba: a UNESCO World Heritage colonial city surrounded by mountains, with a cultural authenticity that Havana’s more visited quarters have lost. Eastern Cuba — Santiago de Cuba and Baracoa in particular — is where Afro-Cuban culture is strongest and where the landscape becomes wilder and more remote. Our clients who travel east consistently say it’s the part of Cuba they remember most.
The cost of a private Cuba trip depends on duration, the mix of private guesthouses and hotels, and the experiences included. Black Tomato builds each itinerary from scratch. Speak to one of our Cuba specialists to discuss what’s possible for your trip.
