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Price Guide
12 Nights - £3,125pp

Flight Inclusive Price from UK

Tour Info
  • International flights from the UK
  • 12 nights accommodation
  • Airport and road transfers
  • Private Excursions
  • English speaking guide

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Cuba & The Dominican Republic

We can Tailor Make Your Itinerary

Pearls of the Caribbean



Santo Domingo

Santo Domingo

Havana, Cuba

Havana, Cuba

Doorways, Cuba

Doorways, Cuba

Trinidad, Cuba

Trinidad, Cuba

Punta Cana, Dominican Republic

Punta Cana, Dominican Republic


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.

At a glance:

  • International flights from the UK
  • All taxes
  • Private airport and road transfers
  • English speaking guide
  • 3 nights Havana, Cuba
  • 2 nights Trinidad, Cuba
  • 2 nights Santo Domingo, Dominican Republic
  • 5 nights boutique beach resort, Dominican Republic
  • Havana city tour
  • Cienfuegos tour
  • Trinidad city tour
  • Santo Domingo tour
  • Dominican Republic beach stay


Day 1:  UK – Havana

Fly from the UK to Havana.

On arrival you will be met and transferred to your chosen hotel.

Overnight Havana.

Day 2: Havana

In the morning your English speaking Cuban guide will pick you up at the hotel.

Transfer to Old-Havana, past the imposing Capitolio and the Grand Theatre. Enjoy a horse carriage ride through the Prado to Cathedral Square.

Enjoy a guided walk through colonial Havana, a UNESCO world heritage site before a visit to the Humidor bar at the Hotel Conde de Villanueva, revealing a fascinating world of cigars.

Enjoy the afternoon at leisure to relax or explore Havana further on your own.

American classic cars are waiting in the evening for a drive along the legendary Malecón on Quinta Avenida to the upper class district of Miramar with its splendid mansions.

Enjoy an aperitif in the garden of the traditional Hotel National, listening to the anecdotes about the US Mafia and other celebrities who stayed at this famous hotel.

Enjoy dinner at a restaurant with a special ambiance and attend the world famous Tropicana show, rounding off a spectacular day in Havana.

Overnight Havana. All meals included.   

Day 3: Havana

Today visit one of the most well-known cigar manufacturers in Havana.

Witness the skillful hands of the Torcedor (cigar roller) at work, producing the world’s best cigars.

From here, attend a rehearsal of the Dance group Havana Queens to get a glimpse into the colourful music and dance culture of Cuba.

See behind the scenes of this highly talented group and take the opportunity to chat with the group members.

Finally this morning, visit Casa Compay Segundo, the house of the famous member of the Buena Vista Social Club.

Enjoy lunch at a charming local restaurant in Vedado before transferring back to your hotel with the afternoon and evening at leisure.

Overnight Havana. Breakfast and lunch included.   

Day 4: Havana – Trinidad

In the morning head towards the centre of Cuba and Cienfuegos,  a city on the south coast known as the 'Pearl of the South'.

Cienfuegos is an attractive city located on a wide bay. Visit the peninsula Punta Gorda and the Moorish 'Palacio de Valle'.

After lunch, stroll acroess the main square Parque Martí, surrounded by magnificent buildings with their French colonial influence.

Visit the splendid Terry Theatre, where Caruso and Sarah Bernhardt once performed.

In the afternoon drive along the panoramic coastal road to Trinidad, a UNESCO world heritage site full of character and famous for its unique colonial architecture.

In the evening visit the Casa de la Trova or the Casa de la Música near the main square to enjoy the essence of Trinidad.

In the evening this is the place to be in Trinidad, where locals and visitors alike mix to enjoy music and dance al-fresco style.

Overnight Trinidad. Breakfast and lunch included.

Day 5: Trinidad

Founded in 1514, Trinidad had its peak during the sugar boom in the 19th century.

Stroll through the cobblestone streets to the idyllic main square surrounded by the mansion of the former sugar barons.

Visit the Museo Municipal at the Palacio Cantero as well as the ceramic workshop Casa del Alfarero.

The afternoon is at leisure to relax or explore further on your own.

Overnight Trinidad. Breakfast and lunch included.

Day 6: Trinidad – Santo Domingo

In the morning take a private transfer back to Havana for your early afternoon flight to Santo Domingo in the Dominican Republic, where you will be met and transferred to your chosen hotel.

Overnight Santo Domingo. Breakfast included.

Day 7: Santo Domingo

Enjoy a full day private tour of the UNESCO World Heritage old town of Santo Domingo.

Overnight Santo Domingo. Breakfast included.    

Day 8: Beach Resort

From Santo Domingo, transfer by private car to your chosen beach destination in the Dominican Republic.

Choose from a tranquil beach hideaway in one the quieter beach destinations in the Dominican Republic or head to one of the busier beach areas such as Punta Cana or Puerto Plata.

Overnight Beach Resort. Board basis as per choice.

Day 9 - 12: Beach Resort

Enjoy the days at leisure, with optional excursions and activities available.

Overnight Beach Resort. Board basis as per choice.

Day 13: Dominican Republic - UK

Private transfer to the airport for your overnight flight back to the UK.

Day 14: Arrive UK

Arrive back in the UK. 

Hotel Suggestions Havana:

Hotel Saratoga

Hotel Suggestions Trinidad:

Casas particulares

Hotel Suggestions Santo Domingo:

Casa Del XVI

Hotel Suggestions Beach:

Zoetry Agua, Punta Cana

12 nights Pearls of the Caribbean:

  • Price from £3,125 pp

This is a guide price only, based on travel in low season.

Prices will vary according to choice of hotel and seasonal airfare and hotel surcharges. Please ask us for any current special offers.

Contact Us:

All of our Dominican Republic & Cuba Tours are completely tailor made and we can put together any kind of Cuba & Dominican Republic Holiday to suit your interests and budget.

Call us now to speak to a Cuba expert about your tailor made Cuba & Dominican Republic holiday.

Call us now on 0333 7000 747

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We're open from 9 until 9 daily and our 0333 number is a local rate number included in most call packages.