The Luxury Collection

From new and exclusive boutique casas particulares and chic 5-star properties with butler service, to delectable fusion-style delicacies in new hidden away private restaurants, Cuba has certainly changed in recent years.

These days, discerning well-travelled guests are genuinely impressed with the quality available and are enjoying luxury Cuba for themselves. Our specialist team offer a personalised service right through from your initial enquiry, to you homeward journey and will help you seek out the best luxury available, including authentic private experiences, and reservations at the best private restaurants. With us, you are in excellent hands to make your Cuban journey truly unique.

We have hand-picked a selection of properties and itineraries that offer you the ultimate in luxury Cuban travel. Whether it’s airport fast track, your personal local contact and local driver, or a dedicated personalised service from start to finish, our concierge team can tailor our service to suit your requirements.

For those who are keen to tour and explore our fascinating island, but prefer the privacy rather than travelling in a group, our selection of our hand-crafted escorted tours can be created privately on any day of the week. You will be accompanied throughout by a friendly and knowledgeable English-speaking guide and why not extend your tour with a beach stay in a luxury hotel or a few nights in Havana either at the beginning or end.

We are experienced and large enough to have our own Havana office and staff throughout Cuba, but we are small enough to know our customers individually by name, and spend time on each booking fine tuning the details and adding our special touches.Call one of travel designers, specialised in Luxury Cuba Holidays

We are very lucky to receive our business mainly through word of mouth recommendations, and repeat business from the fantastic independent travel agents who work with us.

Luxury  Cuba Holidays. Sample Itineraries

For those looking for five-star luxury, the best possible experience in Cuba, we’ve hand-picked five destinations. How you mix them is entirely up to you.

Some of our clients prefer a longer stay by the beach; others prefer to skip Varadero altogether to spend more time in Trinidad or the Cayos. The unspoiled beaches of Cayo Santa Maria are increasingly popular. Trinidad is such a charming colonial town surrounded by verdant mountains and the  sea, that is not uncommon our clients ask us to make the arrangements for them to stay there a few nights and enjoy the lively town culture.

When you speak to us, we can discuss your interests and expectations and suggest the best itinerary based on your plans for this trip

Matthew Osullivan, Captivating Cuba

Create your own destination mix

Luxury itineraries we’ve created for our clients in the past include some of the following variations

  • Havana + Varadero
  • Havana + Trinidad + Varadero

  • Havana + Trinidad + Cayo Santa Maria

  • Havana + Playa Esmeralda

Continue reading our recommended accommodation and experiences in each destination.

Havana. Luxury Holidays

Luxury Cuba Holidays by Captivating Cuba

Enjoy a totally bespoke and personal guided walking tour of Old Havana.

Explore Havana in a private chauffeured old American car, either for a few hours or your entire stay, with a guide if you wish.

Secure seats for world famous ballet and opera at the ornate Havana Teatro and have your personal guide and translator on hand for the evening.

Take a private tour to the UNESCO preserved Vinales Valley and your personal local guide will escort you through Cuba’s world-famous tobacco plantations.

Allow us to make reservations for Havana’s most upscale prestigious restaurants where menus can be planned pre-departure.

Varadero. Luxury Holidays

Luxury Cuba Holidays by Captivating Cuba

A fantastic day privately cruising the clear blue waters off the coast of Varadero. Snorkel in the cool waters and enjoy a seafood lunch.

Enjoy a world class performance of the Buena Vista Social Club with old American car transfers arranged to and from the venue.

Pre-book your tee off times at the unique Varadero Golf Club, a links course with a few challenges in store.

Cayo Santa Maria Holidays

Luxury Cuba Holidays. Cayo Santa Maria. Captivating Cuba

Head east on a private sightseeing transfer to Cayo Santa Maria  with your exclusive guide and stay at  the intimate, luxury  Melia Buenavista Hotel . Enjoy the chance to pre book your upgraded room and your butler will be on hand to look after you during your stay . Alternatively the  Royalton Cayo Santa Maria works really well for those of you that prefer a certain level of style .

Luxury Holidays in Trinidad

Luxury Cuba Holidays. Trinidad, Cuba. Captivating Cuba

Immerse yourself in the history of this UNESCO museum city with a private local guide, who will absorb you into this incredible city.

Head to the hills and explore the Escambray mountains. Meet hill farmers, swim in pools and absorb the peace and beauty of the local scenery.

Reserve dinner in advance at our recommended upscale Trinidad eateries.

Head to the nearby Caribbean beach in an old American car with a hamper filled with chilled drinks, nibbles and a cigar to relax and watch the sunset.

Bespoke Tailormade Luxury Holidays

Many of our clients prefer an entirely bespoke journey to Cuba,
meticulously crafted around their interests

Speak to a Luxury Holidays Specialist

Start designing not a holiday, but a remarkable journey. Build with us a tailor-made experience.
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