Tailor Made Cuba Holidays 2018-03-16T14:47:13+00:00


We create completely tailored, flexible special journeys through Cuba and beyond, and are totally focused on providing unique experiences for our customers.

Captivating Cuba is a totally independent and fully ATOL bonded boutique specialist tour operator, with more than 25 years’ experience providing high-quality tailormade travel to Cuba

Our friendly, experienced and approachable travel designers are passionate about providing authentic journeys throughout Cuba packed with personality and soul, and we really do care that your holiday with us is special.

We have all been to Cuba, experienced our recommendations, and travelled around, and are here to make sure that your journey through the island is meticulously planned and skilfully delivered.Our team have tons of think-outside-the-box creative ideas to make every holiday completely individual, plus we really listen to our customers and focus on the little details that are important to you.

Your Cuba, Your Way

Tailor Made Cuba Holidays. The Luxury Collection by Captivating Cuba.
The Luxury Collection
Tailor-Made Cuba Holidays. Solo Travellers
Tailor-Made Cuba Holidays. Family with Babies and Younger Children
Family with Young Children
Tailor-Made Cuba Holidays. Family Holidays with Teenagers & Older Children
Family with Teens
Cuba Holidays. Budget Travel
Holidays on a Shoestring
Cuba Holidays. Group Travel
Group Holidays
Tailor-Made Cuba Holidays. Weddings and Renewal of Vows
Tailor-Made Cuba Holidays. Exclusive Stag and Hen Parties
Stag and Hen Parties
Tailor-Made Cuba Holidays. Honeymoon
Tailor-Made Cuba Holidays. Notable Occasions
Notable Occasions
Tailor Made Cuba Holidays. Holiday ideas for disabled travellers by Captivating Cuba
Disabled Travel
Tailor-Made Cuba Holidays. Short Breaks
Short Breaks
Tailor-Made Cuba Holidays. LGBT Travel
LGBT Holidays
Tailor-Made Cuba Holidays. Active and Adventurous
Active and Adventurous
Cuba Holidays. Bucket List Inspiration
Bucket List Inspiration

Completely tailored, flexible special journeys through Cuba

We have personally tried and tested our hand-picked recommendations, and have drawn on our experience to create truly unique travel options for our guests.

Tailor-Made Cuba Holidays. Private Escorted Tours, and Small Group Tours
Cuba is a fascinating and unique country to explore on a fully guided small group tour. With numerous UNESCO World Heritage sites, historic towns and cities, spectacular landscapes and the world’s most unique capital city of Havana, the best way to make the most from so many experiences is through a group escorted tour.For those seeking a private experience, we can also organise our tours on an exclusive basis, on any day of the week just for you.

Tailor-Made Cuba Holidays. Multi-Centre Itineraries. Captivating Cuba

Experience the real Cuba in one amazing trip. Multi-Centre Cuba Holidays are, by far, the best and most rewarding way to experience Authentic Cuba, it’s vibrant culture, nature-blessed beaches, beautiful scenery, and welcoming people.

Tailor-Made Cuba Holidays. Cruise and Stay Itineraries. Captivating Cuba

Our carefully selected cruise itineraries offer the more extensive programmes around the Cuba. We can tailor a stay on the island around your cruise, to make sure you don’t miss out on the additional Cuban must-see highlights that you do not visit whilst on the ship.

Tailor-Made Cuba Holidays. Cuba Holiday Types. Captivating Cuba
Completely flexible tailor-made with no restrictions. If it ‘works’ we can arrange it. We can book all products in Cuba and have a range of suppliers. After nearly twenty years completely focused on Cuba, we can do better than any competitor in the UK, and we all have direct destination knowledge. Additional choices include self-drive holidays, salsa, adventure holidays and much more. Take a Look!

We had a fantastic trip. All of the transfers went smoothly, each pick was on time, friendly and professional.  We enjoyed all of the planned restaurants and excursions. We actually managed to pack in a few extra excursions too. So the all inclusive towards the end of our trip was much needed, to relax. We both feel like we have learnt much more about Cuba, the history and culture.

Thank you for your help and making the trip very smooth for us.


We had a great time in both Havana and Guardalavaca and the transfers were seamless.

The Casa Vitrales in Havana was brilliant. The accomodation was clean and the staff ultra friendly (genuinely) and helpful. The Paladars that were booked for us were excellent and the quality of food far exceeded our expectation.We were treated to a slice of real life Habana.

The total contrast of Rio Do Ora was most welcome with good accommodation, amazing staff and an amazing beach. What a place to chill!

Glenn & Dorothy

Thank you for seeing to it that every detail was thought through.  We absolutely love Anay and Enrique (and our driver Enzo) and greatly appreciate their introduction to both the touristic Cuba and the “real” Cuba.  The May Day parade was quite something — so happy we were there for that.  The Casas were gorgeous and Hotel Moka was a very special experience.  Though it may be awhile before I drink another Cuba Libre or Mojito, I truly enjoyed every moment.

I highly recommend Cuba and your services to anyone interested in making the trip.


Speak to Authentic Tailor Made Cuba Holidays Experts

Captivating Cuba is a totally independent and fully ATOL bonded boutique specialist tour operator, with more than 25 years’ experience providing high-quality tailormade travel to Cuba and beyond. Our offices are based in Hertfordshire, UK and we also have staff based in France and Spain, as well as a sizeable office in Havana and staff throughout Cuba.

Ask for a Free Quotation

Amazing Flexibility To Build Beautiful, Unique Experiences

Completely flexible tailor-made with no restrictions. If it ‘works’ we can arrange it. We operate based upon genuine, honest advice with no pushy sales techniques or pressure to book as we would rather get things exactly right for you. We will always let you know what will work well for you and what doesn’t.

Find us on social media for even more inspiration, priceless tips, and holiday ideas.

Cuba Holidays Tailor Made. Captivating Cuba™

Cuba Experiences

We offer a wide range of excursions that can be pre-booked before travel allowing you to plan your holiday without the hassle of arranging your itinerary after arrival. With Cuba so busy, we recommend […]

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Cuba Holidays Tailor Made. Captivating Cuba™

The Casa Particular Experience

Highly recommended and extremely popular, Casas Particulares (often referred to as ‘Casas’) are fully-licensed private bed and breakfast accommodation, with many offering a more boutique hotel-style stay.

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