Inspiring • Authentic • Tailor-Made

01892 515 966



Self-Drive: Explore Cultural Cuba

15 days from £1869 per person

Starting your holiday in Havana, you’ll cruise around the city in a classic car taking in the iconic sights and atmosphere of the country’s bustling capital. From here you will take a short flight to Santiago de Cuba, the birthplace of Cuba’s diverse musical flavours. You’ll pick up your hire car at the airport and drive the length of the country, dropping it back off in Havana at the end of your trip. On the way you’ll stop off to explore Fidel’s rebel camp hidden deep within the Sierra Maestro mountain range, amble through the labyrinth of streets in Camaguey and learn to salsa with the locals in Trinidad. As you drive through the country, you’ll spot countless road signs that celebrate the heroes of the revolution and pass lush green vegetation, sugar plantations and forests of palm trees. Your journey takes you on to the magnificent Vinales Valley where you’ll cycle around the small town before spending your last night back in Havana.

Havana – Santiago de Cuba Sierra Maestra – Bayamo – Camaguey  Trinidad – Vinales  Havana

Itinerary Highlights

Santiago de Cuba is the birthplace of Cuba’s musical diversity, steeped in Afro-Caribbean influences and colonial grand buildings, it’s a vibrant city that’s certainly got a buzz to it.

Hike to Comandancia de la Plata, Fidel Castro’s hide-out, high up in the Sierra Mountain range where the military plans that brought about the demise of the Batista government were formed.

With a passion for music, a flair for creating tasty food and a relaxed town that’s near the sea; Trinidad is often visitor’s favourite place to stay, and it’s easy to see why.

Itinerary: Self-Drive: Explore Cultural Cuba

Today you begin your journey by boarding your international flight to Havana. On arrival you will be met by your private driver and transfer to your hotel in Havana Vieja, the heart of the old town. The rest of the day is free for you to relax at your hotel or head out into Havana Vieja. There are many colonial plazas and plenty of cobbled streets that lead to delightful music halls near to your hotel. (N)
Accommodation: Hotel Raquel (or similar) 
After a brief welcome meeting you will be met by your English speaking guide who will take you on a 3 hour tour of Havana’s iconic sights. You will spend the first 2 hours in a classic car, stopping off at revolutionary landmarks, cruising past colonial buildings and learning about local Cuban life, before embarking on a 1 hour walking tour of the old town. This afternoon, you could ask your hotel for a map and venture out to explore more of Havana’s colonial buildings and impressive monuments. (B)
Accommodation: Hotel Raquel (or similar) 
After breakfast today you will be collected from your hotel by private car and transfer to the airport for your short flight to Santiago de Cuba (flight time approximately 1.5 hours). Upon arrival in Santiago de Cuba you will collect your hire car from the airport and drive to your centrally located hotel, where you will spend the next 2 nights. The rest of the day is free for you to relax or explore the city at your own pace. (B)
Accommodation: Hotel Casa Granda (or similar) 
From your centrally located hotel, you are in the perfect spot to explore the main sights of this Caribbean city. You might choose to visit the Museum of Cuban History, the Bacardi Rum Factory or slip on your trainers and go for a walk around the UNESCO San Pedro de la Roca del Morro Castle which provides stunning views over the bay. If you fancy something a little more relaxed, head to the Trivioli neighbourhood, where Cuba’s finest musicians gather to jam. (B)
Accommodation: Hotel Casa Granda (or similar) 
Later on this morning you will get in the car and drive through a sublime mountain range of green peaks and a humid cloud forest to reach the small and secluded Villa Santa Domingo in the Sierra Mountains (drive time approximately 4 hours). This hotel is the starting point of the hike you will embark on the following morning, so we recommend relaxing amidst the beautiful jungle-clad scenery of your rustic accommodation for the rest of the day. (B)
Accommodation: Villa Santo Domingo (or similar)
After an early breakfast, you will meet your English speaking guide outside your hotel for your hike to Comandancia de la Plata, Fidel Castro’s pre-revolution hide-out. From this mountain base, Castro and his rebels orchestrated the military strikes which brought about the demise of the Batista government. After your hike, you will drive to the low-key town of Bayamo (drive time approximately 1 hour). This evening you might choose to visit Casa de la Trova where you can soak up the lively atmosphere and listen to some live Cuban beats that are guaranteed to get your foot tapping. (B)
Accommodation: Hotel Royalton (or similar)
Bayamo is renowned for housing nearly half of the most significant historical sites in the country. You might choose to take a stroll around the town to discover these impressive sites for yourself this morning, including the birthplace of Carlos Manuel de Cespedes, the cathedral or the Plaza de la Revolucion. Later on, you will begin your drive to Camaguey (drive time approximately 4 hour). When you arrive at Camaguey, spend the rest of the day exploring the maze like streets, which were built this way to confuse invaders and protect the long-suffering residents. (B)
Accommodation: Centrally located Casa 
After breakfast today you will continue your journey on to Trinidad, along more palm-fringed roads (drive time approximately 5 hour). Upon arrival in Trinidad, the rest of the day is free for you to relax or explore at your own leisure. (B)
Accommodation: Centrally located Casa 
After breakfast, you might choose to walk around the cobbled streets of this laid-back town. Pop into local galleries, or have a coffee in Plaza Mayor and watch the locals playing cards outside their colourful Casas. This afternoon you will participate in a salsa dance class with an English speaking instructor. It’s the perfect way to loosen up and learn a few steps that you can practice when listening to a local band later on this evening. (B)
Accommodation: Centrally located Casa 
Today is free for you to explore more of Trinidad at your own pace. You might decide to hire bikes and cycle out to the peaceful Playa Ancon, or take a scenic train ride into Valle de los Ingenios. (B)
Accommodation: Centrally located Casa 
After breakfast today you will drive to Vinales (drive time approximately 6 hours). Although a long journey, there are plenty of opportunities to stop off and stretch your legs. You might choose to travel via Santa Clara, home to Che Guevara’s mausoleum which is worth a visit. Upon arrival in Vinales you will be greeted by your friendly Casa hosts who will make you feel right at home. Spend the rest of the day relaxing at your Casa. (B)
Accommodation: Centrally located Casa 
Later on this morning you will meet your English speaking guide who will take you on a bicycle tour of the town. During your tour you’ll learn more about the small settlement as you cycle through lush and scenic valleys and past red-earthed fields. This afternoon you might decide to explore the pretty countryside town or go on a walking tour through the nearby tobacco fields where you can learn how to roll a Cuban cigar. (B)
Accommodation: Centrally located Casa 
After breakfast today you will drive back to Havana (drive time approximately 2 hours). When you arrive back into Havana you will drop off your car and make your own way to your hotel. You might decide to spend the rest of the day wandering around more of Havana’s cobbled streets or choose to have a drink at one of Hemmingway’s old haunts. (B)
Accommodation: Hotel Raquel (or similar) 
Today is free for you to explore Havana or relax at your hotel until you are collected and transferred to the airport by private car for your international flight back to the UK. (B)
Today you will arrive back into the UK, where you will continue your journey home. (N)
**KEY: N = No meals, B = Breakfast, L = Lunch, D = Dinner

What To Do Next?

We design unique, tailor-made holiday itineraries to suit you, by combining your ideas with our knowledge and experience. Once you have an idea of what you’re looking for, or if you require some advice, please call us or complete the enquiry form online for a quotation.

What's included

  • International flights from the UK
  • Domestic flights
  • Private car and driver
  • Sightseeing with local English speaking guides
  • Car hire as specified

What's not included

  • Cost of visas
  • Travel Insurance
  • Expenses of a personal nature
  • Meals unless specified

Guide to Price

The above price is based on two people travelling together and sharing accommodation in low season. The price is only a guide and can vary according to selected airlines, hotels and date of travel. If you wish to travel with your family, friends or on your own we will be very happy to assist you with your arrangements.

Popular Holidays

Cuba Holiday Review

I want to say thank you again for all of your help in arranging our dream honeymoon.

We LOVED every second of it and were desperate for it not to end. I can't quite believe we have ticked Cuba off our bucket list. Amazing!

TR & RW - Cuba - April 2018

Related Blog Post

Experts in Tailor-Made Holidays

For over 30 years, Pettitts Travel have led the way in creating authentic, tailor-made holidays. Our knowledgeable team have first-hand knowledge of our destinations and no two itineraries we prepare are the same.

Please call us for more information or complete the online enquiry form to request a quotation.

01892 515 966 Request a Quote

Head Office: 8-9 Orchard Business Centre, North Farm Road, Royal Tunbridge Wells Kent. TN2 3XF

× logo

Welcome to Pettitts Travel, the new name for
Medway Leisure Travel.

Everything you expect from Medway Leisure Travel is included here on the Pettitts Travel website... plus lots more!