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A Taste of the Caribbean with Cuba & Jamaica

Havana, Vinales Valley, Trinidad & Montego Bay

Best time to travel
Nov -July
Ideal length
14 nights
Perfect for
From (incl flights)
€6,199 pp

At a glance

  • International flight from Dublin to Havana and home from Montego Bay.
  • All private transfers, internal flights and guiding requirements.
  • 14 nights’ accommodation in handpicked properties in Cuba and Jamaica.
  • Sit in the back of 1950s American open top car and take in the sights as you drive around Havana.
  • Hike through the Vinales Valley and also visit a tobacco farm and in Santa Clara visit the Che Guevara mausoleum.
Let's plan your trip!


Boasting a rich Latin-influenced history and a lively lifestyle of salsa dancing, vintage cars and cigars, Cuba is a unique destination amongst the sun-soaked Caribbean. In this suggested itinerary, we have combined the largest country in the Caribbean, Cuba with the wonderful beaches of Jamaica. Start your journey in the birthplace of the Mojito, Havana where you’ll explore the city by open-top car, you’ll also visit the Vinales Valley, Trinidad and Santa Clara along the way. We’ll then transport you to the brilliant beaches of Jamaica where you’ll spend your final few days unwinding in a beautiful handpicked resort. This itinerary is ideal for those seeking something a little different.

View all of our luxury holidays to Cuba & Jamaica.

Trip Overview

Fly from Dublin to Havana, Cuba’s capital city.

On arrival, your driver will greet you and take you to your accommodation where you’ll spend the next three nights. We will share with you the best things to see and do, as well as the best places to eat during your stay.

Enjoy a guided city tour of colonial Havana.

Walk in the footsteps of Havana’s colonial past visiting the four key squares of Old Havana, a UNESCO World Heritage site. Visit Plaza de Armas, Plaza San Francisco de Asis, Plaza Vieja, and the Plaza de la Cathedral with your expert guide offering insights into history along the way.

Havana, Cuba
Today, you’ll enjoy a panoramic city tour in a vintage open top car.

Explore 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
You will then journey by private vehicle to Vinales.

Check-in to your hotel on arrival, you will spend the next two nights here.

Vinales, Cuba
Enjoy a farm to table tobacco guided tour!

From growing it and drying it, to rolling it and smoking it. This is the in-depth tour of tobacco from seed to cigar. Walking into the lush countryside, you will visit the tobacco plantations where they still plough with oxen, see the famous drying houses and have a tobacco farmer show you how to roll a cigar.

Tobacco plantations, Cuba
Today, you will enjoy hiking the Vinales Valley.

This trek is named after the local traditions of a small number of residents that live in the Viñales Valley and believe in the healing properties of water. The walk itself is around 4kms long and along the way, you will see the dramatic landscape of this stunning natural area declared a UNESCO world heritage site in 1999.

Viñales Valley, Cuba
It’s time to leave Vinales and transfer to Trinidad.

On arrival, check-in to your accommodation where you’ll spend the next three nights.

Trinidad, Caribbean
See the best of Trinidad on a guided walking tour.

This walking tour will introduce you to this UNESCO World Heritage Site. Your expert guide will explain the history of the town, while visiting its architecture highlights and give you insight into its fascinating history in the colonial era, and during the years after the revolution.

Cuba, Trinidad
Your driver will then transfer you to your next destination, Santa Clara.

You’ll spend overnight in a handpicked property in this city that is most famous because of Che Guevara and the history of Cuba’s revolution.

Che Guevara statue, Santa Clara
Get to know Santa Clara through the eyes of your local guide.

Enjoy a guided walk through the footprint of this city. Along the way, you’ll visit Parque del Carmen, Tren Blindado, Parque Vidal, Mejunje, La Caridad Theatre and Revolution Square.

Revolution Square, Santa Clara
Your driver will collect you at Santa Clara and transfer you to Havana.

Check-in to your accommodation where you’ll stay overnight. Enjoy some time at leisure in Havana, exploring the sights and sounds of this destination.

Havana, Cuba
It’s time to relax as you fly from Havana to beautiful Montego Bay, Jamaica.

Enjoy the next four nights, unwinding in a beautiful handpicked resort. Throughout your stay, enjoy the fabulous sunsets, coastal views, excellent water sports and the stunning spa.

Montego Bay, Jamaica
Privately transfer to the airport for 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

Round Hill Hotel & Villas

Round Hill Hotel & Villas

Round Hill Hotel & Villas is an elegant hotel set at the edge of the Caribbean Sea. This renowned Caribbean resort is an ideal retreat for families and couples alike with a nostalgic atmosphere.

More details

Suite Florencia

Suite Florencia

Suite Florencia is a colonial style house located in the heart of Santa Clara city. The house, built in 1930, was completely renovated in 2016.

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What people are saying

“We recently travelled to Barcelona and Mallorca with the expert help of Oroko and will never book a holiday any other way again! The staff were so friendly and knowledgable and made the process of booking extremely easy. The travel pack was very impressive with our luggage tags, complimentary treats for the airport, and comprehensive guide to both areas with recommended restaurants which didn’t disappoint. I couldn’t speak highly enough of our experience with this company and would highly recommend to friends.”

Orla & partner – Mallorca 2019


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