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Caribbean Pearls

Combine Cuba & the Dominican Republic and experience three of the most vibrant and colourful destinations in the Caribbean before enjoying a few nights relaxing in an unspoilt boutique beach resort in the Dominican Republic.

Enjoy 3 nights in Havana with its unique ambiance including American classic cars, art, music, street life and architecture.

From Havana head to Trinidad via Cienfuegos for 2 nights in the UNESCO World Heritage town of Trinidad, one of the most atmospheric locations in Cuba and home to some of the finest colonial-era architecture in the Caribbean.

Return to Havana and fly to Santo Domingo in the Dominican Republic, the very first city founded in the Americas.

Enjoy 2 nights to explore the charming UNESCO World Heritage Old Town.

From Santo Domingo, head to the beach to relax in a boutique beach resort in the Dominican Republic for a few days. Choose from quieter destinations such as Samana and Barohana or head to a busier area such as Punta Cana or Puerto Plata.

This Cuba & the Dominican Republic holiday is ideal for those looking to discover some of the Caribbean's most historic locations combined with some time to relaxin an unspoilt beach destination.

Kudadoo Water Villa.png

Kudadoo Water Villa.png

Kudadoo Water Villa.png


Passionate, rhythmic, sultry, independent - Havana is a destination which evokes many different images and looms large in the panthen of great travel destinations.

As Cuba opens itself up more to the West, Havana will inevitably lose some of it's mystery and allure, so now may well be a good time to move Havana to the top of the list of must-do destinations.

Cuba on the whole is dominated by large, functional hotels (blame the Russians) but there are a handful of excellent boutique hotels in Havana which will enhance your stay in Cuba's capital.

Santo Domingo

Santo Domingo is the largest, most animated, cosmopolitan and people-freidnly city in the Caribbean and Central America.

The centre of this charming colonial city is a UNESCO World Heritage Site and very easy to get around, just 16 short streets with bountiful examples of architecture dating from the 16th to the early 20th centuries.

Cobblestone lanes and iron street lamps lead to many small museums, shops, restaurants and boutique hotels in the centre of town.

Tailor Make This Holiday

£3,425 pp

Low Season

£3,695 pp

High Season

12 nights Accommodation, Car Rental, Flights from the UK


Low Deposit

Flexible Bookings


ATOL Protected

Travel Trust Protected

Call Now: 0333 7000 747

Tailor Made Cuba Holidays | Jasmine Holi

Whatever your Caribbean, we've got you covered.

Tailor Made Luxury Cuba Holidays

The Best Tailor Made Luxury Cuba Holidays

Whether you're looking for a Tailor Made Tour of Cuba, a luxury resort on a stunning Caribbean beach or few days in Havana combined with time on the beach, we have plenty of options for you.


All of our Cuba Holidays are tailor made and we can design any itinerary to suit you, whatever your interests. You will have your own car and driver-guide to escort you across the island.


Our focus always has been and continues to be on boutique and luxury hotels Cuba and in all of our Caribbean holiday destinations. We have our recommended hotels in Cuba, but if you have a preferred hotel in Cuba, just let us know.

Remember that all of our holidays to Cuba from the UK have been Travel Trust and ATOL protected since we opened our doors in 2007, giving you peace of mind in booking your holiday with us.

Call Now: 0333 7000 747

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