Luxury Cuba Holidays
Cuba is the Caribbean’s largest island and one of its most captivating. From the faded grandeur of Havana’s colonial streets to the lush valleys of Viñales and the powder-soft sands of Varadero, every corner of Cuba tells a different story. This is a country of contrasts – where classic cars cruise past cutting-edge art galleries, and centuries of history sit alongside a vibrant, ever-evolving culture.
A luxury Cuba holiday goes beyond the must-see sights. Stay in boutique hotels and private casas that combine charm with comfort, explore with expert local guides, and enjoy unique experiences – from meeting tobacco farmers in Pinar del Río to discovering the rhythms of salsa in Havana. With tailor-made itineraries, you’ll uncover Cuba’s hidden gems while travelling in style.
Whether you’re drawn to Havana’s music-filled nights, the mountains of the Escambray, or the quiet beaches of the south-east, Cuba offers a journey like no other.
Ways To Explore
Private Travel
Cuba is a country of contrasts: colonial beauty, lush countryside and music at every turn. Share your vision with me and I’ll craft a luxury Cuba holiday that’s uniquely yours, or take inspiration from the itinerary I’ve curated below.
Small Group Journeys
In Cuba, travelling with a small group can open doors that might otherwise remain closed – from private music sessions in Havana to meeting farmers in Viñales. I’ll help you find the journey that suits you best, connecting you with like-minded travellers and expert guides who bring every moment to life. I’ve highlighted one below, but there are other exceptional journeys I can match to your style.
Small Group Journey
Cuba comes alive through its people, and your local guide is the key to unlocking its spirit. More than a tour leader, they’re a storyteller and cultural insider who’ll connect you with farmers in Viñales, musicians in Trinidad and the revolutionary history of Havana.
Over 9 days and 8 nights, you’ll travel with a group of no more than 12 like-minded companions, staying in a mix of feature hotels and premium guesthouses. It’s an authentic journey with comfort, camaraderie and expert guidance at every step.
I’ve highlighted one option below, but there are other exceptional journeys I can match to your style.
3 nights – Havana (split 2 + 1)
Stay at a feature property such as the Grand Muthu Havana (or a similar premium hotel) with rooftop views and a pool to unwind. Begin your adventure with a welcome dinner, then see the city in style: a vintage car tour along the Malecón and Revolution Square, followed by a guided walk through Old Havana’s plazas and cathedral quarter. End your trip back here for one last evening in the capital.
2 nights – Viñales
Settle into a premium guesthouse (casa particular), where Cuban hosts combine warm hospitality with comfort. Explore the valley on foot, learning about the region’s famed tobacco farms before a hands-on salsa lesson. In the evening, dine at an eco-farm perched above the valley with sweeping views.
1 night – Cienfuegos
Overnight in a charming local hotel such as Hotel Union, right in the historic heart of this pretty coastal town. Take a sunset stroll along the waterfront and visit the Moorish-inspired Palacio de Valle.
2 nights – Trinidad
Stay in a premium guesthouse, close to the cobbled streets and pastel houses of Trinidad. Enjoy a guided orientation, time to relax at Playa Ancón if you wish, and a festive dinner at a local farmhouse with live music. On the return to Havana, pause at the Valle de los Ingenios viewpoint and visit the Che Guevara mausoleum in Santa Clara.
Tailor-Made Private Travel
This luxury holiday to Cuba incorporates all the essentials. From energetic Havana to the immaculate beaches of Cayo Santa María, from the delightfully laidback Viñales Valley to the colonial gem that is Trinidad, this journey showcases Cuba’s highlights in one unforgettable trip.
Perfect for
First-time visitors eager to experience the must-see destinations of Cuba.
If you’d like something different
Add a stop at Las Terrazas en route from Havana for a night in Cuba’s famous eco-village, a UNESCO Biosphere Reserve with forest trails, waterfalls and a community spirit unlike anywhere else on the island.
4 nights – Havana
Your Cuban adventure begins in the capital, where you’ll check into the charming Hotel Florida in the heart of Habana Vieja. Start Hemingway-style with a daiquiri in the bar before venturing out to discover the city’s rhythm. By day, explore the streets on a guided walking tour and a classic car ride that sweeps you past Revolution Square, the Malecón and the Cathedral. By night, experience the glamour of Tropicana, Cuba’s legendary open-air cabaret, alive with music and dazzling choreography.
2 nights — Viñales
Swap city life for the countryside with two nights at La Ermita, a hotel with views across Viñales’ dramatic mogotes and patchwork of tobacco and coffee plantations. Spend your days exploring the valley on foot, horseback or even by bike, stopping to meet local farmers who still use traditional methods. In the evenings, relax by the pool and take in the sweeping vistas as the sun sets over this serene corner of Cuba.
3 nights — Trinidad
Step back in time in colourful Trinidad, where cobbled streets, pastel façades and colonial squares reveal a town rich in character. Your base is the Iberostar Grand Hotel Trinidad, a colonial-style boutique property close to the action. Explore the town on a guided walk, learn a few salsa steps with a local teacher, and by night, join the locals at Casa de la Musica for outdoor dancing under the stars. During the day, you’re perfectly placed to trek in the Escambray Mountains or relax on the golden beaches of the Peninsula de Ancón.
3 nights – Cayo Santa María
End your holiday in barefoot luxury on the island of Cayo Santa María. Your stay at the Royalton is all about indulgence, with sprawling pools, a sleek spa and an all-inclusive offering of fine dining and cocktails. Spend your days drifting between the white-sand beach and the turquoise sea, enjoying water sports or simply basking in the Caribbean sunshine.
Prices & Planning Your Holiday
Airlines and hotels are constantly updating their offers, so I do not display fixed prices on my website. This allows me to ensure you always receive the very best value when you enquire.
The process is straightforward. Share your holiday plans using my enquiry form and within one working day, I will arrange a no-obligation consultation by phone, video call or email. If you are local to Tavistock, I would be delighted to meet in person at a time that suits you. Following our conversation, I will prepare a personalised quotation tailored entirely to your plans. I can also look after the finer details, from flights and transfers to excursions and even airport parking.
Trusted Partners & Peace of Mind
These two itineraries give you a taste of what’s possible in Cuba. One offers the camaraderie of a premium small-group journey, led by expert local guides. The other is a private, tailor-made escape designed exclusively around you and your family. Both are created with my trusted partners, and whichever way you’d like to travel, I’ll make sure your Cuban adventure is unique and truly memorable.
I am part of The JLT Group, which means you enjoy the personal service of an independent travel advisor, backed by the security of an award-winning company. Every holiday I arrange is fully protected, and my support continues before, during and after your trip, whether you need reassurance, a change of plans or help with the unexpected.
How I Can Help
Choosing between Cuba’s captivating destinations can feel overwhelming — from Havana’s colourful energy to Viñales’ rolling valleys, Trinidad’s colonial charm and the calm beaches of Cayo Santa María. Each offers its own rhythm, character and pace.
I take the time to understand how you like to travel, the level of comfort you want, and the kind of experiences that make a holiday feel truly special. With access to trusted partners across Cuba, I can tailor every detail — from boutique hotels to guided experiences, flights and transfers.
Get in touch and let me design the Cuba holiday that feels like yours.
Frequently Asked Questions
Do I need a visa to travel to Cuba?
Yes. UK travellers need a Cuba Tourist Card (often called a visa) to enter the country. I can arrange this for you as part of your booking, so there’s no need to worry about paperwork; it’s all taken care of before you fly.
How long should my passport be valid for?
Your passport must be valid for at least six months from the date you arrive in Cuba. It’s also worth checking you have at least one blank page for the entry stamp.
Do I need travel insurance?
Yes. Travel insurance is a legal requirement for all visitors to Cuba. I recommend choosing a policy that covers medical care and flight delays. You may be asked to show proof of insurance when you arrive at Havana Airport.
Are there direct flights from the UK to Cuba?
Yes. Several airlines, including Virgin Atlantic, offer direct flights from London to Havana. I’ll include the most convenient route and schedule when planning your holiday, along with private transfers on arrival.
Can I travel via the USA?
Not directly. If you’re planning to combine destinations, you’ll need to fly to Cuba via another country such as Mexico or Canada, as transiting through the USA on the same trip can cause complications under US travel regulations.
Will my bank cards work in Cuba?
Cuba is largely a cash-based economy. Some UK-issued Visa and Mastercard debit cards work, but it’s best to bring cash (euros are preferred) to exchange locally. I’ll guide you through the best approach before you travel.
Is Cuba safe for British visitors?
Yes. Cuba is considered one of the safest destinations in the Caribbean, and petty crime is rare in the areas most travellers visit. As with any trip abroad, a little common sense goes a long way, and I’ll share trusted local tips before you go.
When is the best time to visit Cuba?
Cuba enjoys warm weather year-round, but the most pleasant months for travel are between November and April when the climate is dry and sunny. If you prefer quieter streets and good value, May and early June are also lovely times to visit.
Can I use the internet or mobile data easily?
Wi-Fi is improving across Cuba, but it’s still not as reliable as in Europe. Most hotels now offer internet access, though connection speeds vary. I always say to treat it as part of Cuba’s charm, a rare chance to switch off and be fully present.
Are any vaccinations required?
No specific vaccinations are required for entry from the UK, though it’s wise to ensure your routine travel immunisations (like tetanus and hepatitis A) are up to date.
Let's plan your perfect trip
Your next holiday doesn’t have to stay a dream. Whether it’s a bucket list adventure or a simple escape to recharge, I’ll handle the details so you can enjoy the moments.
With expert planning, trusted partners and 24/7 support, your holiday is in safe hands.
Fill in the form to book your free, no-obligation consultation and let’s plan your next escape.
If you prefer, email Rachael@blueturtleescapes.co.uk or phone me on 07736296930.