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From Havana to Cuba’s Tropical Islands

Havana, Trinidad & Cayo Guillermo

Best time to travel
Nov – July
Ideal length
10 nights
Perfect for
From (incl flights)
€5,199 pp

At a glance

  • International return flights from Dublin to Havana, Cuba.
  • 10 nights’ handpicked accommodation in Havana, Trinidad and Cayo Guillermo.
  • Sit back and see the sights of Havana as you’re driven around in a 1950's American vintage open-top car.
  • Explore charming Trinidad at a leisurely pace on a walking tour.
  • Spend time in beautiful Cayo Guillermo swimming in crystal clear waters and relaxing on the sandy beach.
Let's plan your trip!


Get ready to explore the luxury side of Cuba. Begin your journey in vibrant Havana where you’ll explore the city in a vintage open-top car, before you start your exploration of both Trinidad and Cienfuegos. Your journey ends in beautiful Cayo Guillermo, a tropical island in the Jardines del Rey archipelago where you’ll spend your final days relaxing and soaking up the sun. Throughout this itinerary, you will be staying in superb luxury handpicked accommodation. We have also included handpicked excursions, guided walking tours and you will accompany a local chef to learn how to make a real Cuban mojito and feast on typical Cuban food with a twist. A superb suggested itinerary for those who want to a touch of luxury in Cuba.

View all of our luxury holidays to Cuba.

Trip Overview

Depart from Dublin to Havana, Cuba.

Your driver will greet you on arrival and privately transfer you to your luxury accommodation in Havana where you’ll spend the next three nights.

Enjoy a privately guided tour through Havana.

Discover Havana like a local as you accompany your guide and walk in the footsteps of Havanas colonial past. Visit the four key squares of Old Havana, a UNESCO World Heritage site as well as Plaza de Armas, Plaza San Francisco de Asis, Plaza Vieja and the Plaza de la Cathedral as your expert guide offers unique insights into its history along the way. In the evenings, enjoy dinner in an OROKO recommended restaurant.

Havana, Cuba
Next, discover the city in a vintage open-top car.

Enjoy a tour of the city in an open-top vintage car taking in all the main sites including the Havana Almendares forest, Cristobal Colon Cemetery, hotels National and Riviera.

Oldtimer, Havana
Experience a unique food your at Jibaro.

With your chef Diana, you will visit a produce market and a store to learn about the different ways that Cubans have access to food. Then enjoy some lunch at Jibaro, where you will learn how to make a real Cuban mojito and feast on typical Cuban food with a twist. Why not also pop around the corner to see one of the most spectacular churches in Havana, Iglesia de las Mercedes.

Cuban Mojito
Next, privately transfer to Trinidad via Cienfuegos.

Your driver will drop you off at your accommodation where you’ll spend the next two nights.

During your stay, enjoy a privately guided tour of Trinidad.

Your guide will introduce you to this UNESCO World Heritage Site and will explain the history of the town while visiting its architectural highlights and give you insight into its fascinating history in the colonial era and during the years after the Revolution.

Trinidad, Cuba
It’s time to transfer to the airport and fly to beautiful Cayo Guillermo, a tropical island in the Jardines del Rey archipelago.

Spend the next four nights in a one-of-a-kind resort and experience an authentic Caribbean stay. Swim and snorkel in the clear, shallow coastal waters and relax on the beautiful sandy beaches.

Cayo Guillermo, Cuba
You’ll privately transfer back to Havana and overnight before your flight home.

Arrive in Dublin.

Tailoring your holiday

OROKO Itineraries are created with you in mind and no two are the same. These can be used to help plan your trip - or we can design a completely different itinerary to suit you.

Let's plan your trip!

Where to rest your head

Looking for the best accommodation? We've got the contacts

Hotel Manzana Kempinski

Gran Hotel Manzana Kempinski

In the heart of UNESCO-protected Old Havana, the Gran Hotel Manzana Kempinski is a Havana’s first ultra-luxury hotel set in the historic 20th-Century Manzana de Gomez building.

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Iberostar Heritage Grand Trinidad

Iberostar Heritage Grand Trinidad

With classic colonial architecture and décor, trendy restaurants and bars and a friendly atmosphere, Iberostar Heritage Grand Trinidad is is a charming adults-only hotel located in the heart of Trinidad.

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Hotel Kempinski Cayo Guillermo

Hotel Kempinski Cayo Guillermo

Cayo Guillermo Resort Kempinski is a unique, one-of-a-kind resort nestled in the tranquillity of Cayo Guillermo in Cuba. This serene and contemporary hideaway offers a refreshing and authentic Caribbean experience.

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What people are saying

Aisling and her team are just outstanding at what they do. They have an incredible knowledge of the travel industry and I have had the best experience with OROKO Travel. From the first phone call to enquire about a holiday to the call we received after our holiday, I cannot say enough about this company. They are truly outstanding. I really look forward to working with them again in 2022 and hopefully for many years to come. There is no travel specialists like OROKO. 5 stars, just fantastic!

Sinead & family – Croatia, September 2021


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