Tailor-Made Holiday

A holiday to Eastern Cuba

A journey through Cuba's revolutionary past

16 days

from £4,835pp (excluding flights)

Few venture in this direction. A handful of charters fly into Holguin with holidaymakers making a beeline for the beaches of Guardalavaca, but this holiday idea takes you away from the masses deep into the island interior on a revolutionary mission.

  • Visit sleepy towns like Bayamo and Baracoa with a yesteryear quality
  • Hike in the Sierra Maestra and visit the remaining shacks of Fidel’s HQ
  • Discover Santiago de Cuba with its strong Afro-Cuban culture and rich music scene.
  • Stay on undeveloped Playa Maguana, a great alternative to the Cuban all-inclusive beach resorts.

If you have visited Cuba before or really want to get an insight to the Revolution, then this alternative journey idea will take you into the eastern Cuban heartland, an area that witnessed fierce fighting and the snow-balling of Castro’s military campaign.

It would not be right to exclude Havana on any trip to Cuba and so we’ve also included time here, in one of the world’s most exciting capital cities. A flight to Holguin and short transfer brings you to the little-visited eastern Cuba town of Gibara, from where you’ll trek in the Pinares de Mayari and take a day trip to beautiful yet quirky Cayo Saetia with its menagerie of non-endemic animals. Continue, via Bayamo, up into the Sierra Maestra to visit Castro’s mountain HQ before dropping down to the coast to explore colonial plazas, Santeria and the music houses of Cuba’s second city, Santiago de Cuba. The journey concludes with a few nights on Playa Maguana, the antithesis of Cuba’s typical large beach resorts – a handful of wooden cabanas located on an idyllic stretch of sandy beach. It’s an isolated location but accessible to the wonderfully laid-back town of Baracoa and great hiking in the Humboldt National Park. Return to Havana for a final night and vintage car tour of the city.

This itinerary certainly takes you beyond the ordinary, to an area of Cuba that is relatively free of tourists but holds a great variety of interest for the intrepid traveller. Roads and general infrastructure are not always great but you will certainly be rewarded for your efforts.


For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Price Excluding Flights £Flight cost from 
£ 4835 £ 660
  Click here to see what is included/excluded

what is included

  • All accommodation
  • Internal flights
  • International flights as detailed
  • Sightseeing with private guide as per the itinerary
  • Transfers as detailed

what is excluded

  • Gratuities
  • Travel Insurance
  • Visas


Itinerary at a glance

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Day 1

Fly London to Havana

You will be staying at Hotel Saratoga, Bed & Breakfast

Day 2

Old Havana Walking Tour
Half day walking tour of Old Havana. Walk in the footsteps of Havana´s colonial past visiting the four plazas of Old Havana, a UNESCO world heritage site. Visit Plaza de Armas, Plaza San Francisco de Asis, Plaza Vieja and Plaza de la Cathedral with your expert guide offering insightful history along the way.

Romantic, beautiful and fascinating, Havana is a must for anyone's visit to Cuba. Fortifications, colonial buildings and churches tell of a rich history, whilst a Communist regime and erosion from the sea lend a faded glory to the city. The old heart gives way to Soviet starkness, whilst the 1950s playground of Vedado, neighbours the historic mansions of Miramar. Quite simply, stunning.

Havana Art Tour
Leave your hotel with your guide for an Art Tour. You will visit 4 emerging Cuban artists in their studios. Get behind the façade and interact with this thriving community. We can adapt the visits depending on your particular interest. Photography, sculpture or painting. Specify whether you would like to see well known or up and coming artists.

You will be staying at Hotel Saratoga, Bed & Breakfast

Day 3

Classic Car drive
4 hour drive in a vintage open top car in a genuine 1959 Buick.

Your tour can be tailored to take in the highlights of Havana as well as themed around Hemingway. En route you´ll be able to take panoramic shots from El Morro, the fortress at the mouth of Havana harbour, the Malecon, iconic cinemas such as La Rampa & Chaplin and the impressive Bacardi building, Revolution Square; home to a large image of Che Guevara, the woods in Kholy, Playa and the river Almendares.

Cruising with the roof down along the malecon at sunset while listening to Sinatra is a magical experience.

Fly Havana to Holguin

Drive from Holguin to Gibara (Road Journey)

The sleepy town of Gibara, whitewashed houses topped with red riled roofs, is an undiscovered gem with the largest amount of artists per capita in Cuba, and is popular with independent travellers seeking something similar to remote Baracoa, but more accessible - Gibara is only 40 minutes by car from Holguín. Gibara explodes with activity during the Low Budget International Film Festival (Festival Internacional de Cine Pobre), which has been going for more than a decade: the Sundance of the Caribbean. Concerts, theatre and exhibitions add to the cinematic programme.

You will be staying at Ordoño, Bed & Breakfast

Day 4

Trekkking in Pinares de Mayari
Leave your hotel with your guide this morning for a full day trekking in the hills of the Pinares de Mayari, a beautiful countryside of pine-forested mountains offering panoramic views down towards the north coast. This is a tremendous area for hiking, swimming under waterfalls and bird watching. Lunch will be included.

You will be staying at Ordoño, Bed & Breakfast

Day 5

Day trip to Cayo Saetia
Drive with your guide to Cayo Saetia this morning to explore an island that was artificially created in the early 20th century when the tip of this peninsula was isolated by cutting a channel to link the bays of Levisa and Cabonico. A small draw-bridge now offers vehicular access. Saetia is fringed by 12 sandy beaches and a coral reef that offers some excellent diving. Wildlife is a quirky mix of endemic and species imported from around the world (deer, zebras, antelopes, boars, buffalos, ostriches, turkeys, zebras, tocororos, macaw, antelopes, jutias and wild bulls). Lunch is included today.

Day 6

Drive from Gibara to Sierra Maestra (Road Journey)

You will be staying at Villa Santo Domingo, Bed & Breakfast

Day 7

Fidel's Hideout
A 2-3 hour gentle hike through the Sierra Maestra Mountains to reach Fidel's hideout - the organising and staging post for the Cuban revolution. Visit the preserved huts where Fidel and Che Guevara led the group of revolutionaries to ultimate victory in the Cuban revolution. Even if revolutionary history is not your thing, the views alone are worth the hike with spectacular scenery in crisp mountain air.

You will be staying at Villa Santo Domingo, Bed & Breakfast

Day 8

Transfer to Santiago de Cuba

Descend from the cool peaks of the Sierra Maestra to the tropical city of Santiago de Cuba on Cuba's far eastern coast, a journey of around 3.5 hours.
You may wish to stop on the way to visit the Church of La Virgen de la Caridad del Cobre, dedicated to Cuba's patron saint, previously visited by both former popes John Paul II and Benedict XVI.
Learn the mystic story of the Virgen de la Caridad, climb the hill to the Cimarrón monument which is a sculpture created in bronze and iron to honour one of the earliest slave revolts that took place in the country. Up there, you will also have the opportunity to enjoy a beautiful view to the blue lagoon.

Physically closer to Kingston, Jamaica than to Havana, Santiago de Cuba is the stronghold of Afro-Cuban culture in Cuba and has a fearsome musical, cultural and political heritage. Overpoweringly hot and humid, Santiago swings to its own laidback vibe.

Though it's Cuba's second city, it feels compact, with a handful of key monuments and nightspots. Don't miss the Casa de la Trova, where the city's legendary rumba can be heard. Socialist to the core, Santiago was a key stronghold during the nascent stages of the Revolution.

The Moncada Barracks, where Fidel led a failed coup in 1953, are worth a visit, as is the Castillo del Morro, the old fortress, a romantic place to watch the sunset with panoramic views.

On the cultural side, don't miss Santiago's wealth of smaller museums, such as Museo Emilio Bacardi Moreau, the home of the cultural treasures of the Floridian émigré and rum king (he collected everything from Egytian mummies to creepy artifacts of slavery). The best time to visit Santiago is in sticky August, when the city explodes in a long, colourful, summer carnival.

You will be staying at San Basilio, Bed & Breakfast

Day 9

City tour
Santiago de Cuba was declared a National Monument on October 10, 1978. Spend the day with a guide, visiting the main historical and cultural points of interest of the city including Revolution Square and the Moncada Barracks and its museum of July 26, the Revolution Square and other historical, religious and cultural sites.

You will be staying at San Basilio, Bed & Breakfast

Day 10

You will be staying at San Basilio, Bed & Breakfast

Day 11

Drive from Santiago de Cuba to Baracoa (Road Journey)

Full day transfer/tour that hugs the Caribbean coast past Guantanamo Bay before cutting over the Sierra de Puriel mountains in an impressive set of switch backs that will finally drop you down into the wonderfully isolated town of Baracoa.
Stop off here to explore the town with your guide. Visit the Catholic and Hotel Castillo, the 1st fortress built to defend the city from pirates. There are extraordinary views over the city from the battlements.
Then visit La Punta fortress before continuing north for a few days on the coast at Maguana.

You will be staying at Villa Maguana, Bed & Breakfast

Day 12

You will be staying at Villa Maguana, Bed & Breakfast

Day 13

You will be staying at Villa Maguana, Bed & Breakfast

Day 14

Fly Baracoa to Havana

You will be staying at Hotel Saratoga, Bed & Breakfast

Day 15

Havana Time to Yourself
Time to yourself to enjoy ’La Habana’.

Highlights of the old town include the Plaza de la Catedral, the Malecon lining the sea front, the Plaza de Armas and the Castillo del Morro.

There is also an excellent market during the weekend. However to see all sides of the city a visit to the Communist aspects such as the Plaza de la Revolucion and its concrete surroundings is a must.

Explore the streets of the old town, enjoy a Mojito in Hemingway’s favourite bar, listen to the jazz played in the plazas and watch the world and the 1950s cars go by.

Fly Havana to London


Below you can see some of the wonderful places we recommend you stay on your journey.

Hotel Saratoga

Hotel Saratoga

Hotel Saratoga is an elegant, neoclassical-style building with a legendary status for fine cuisine, eye-catching decoration and good service....

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Villa Maguana

Villa Maguana

Located next to 2kms of white-sand beach of Maguana - possibly the most beautiful in Cuba - sit four cottages, each housing 4 rooms, perfect for boho beach living....

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For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Destination Experts

Our experts have unrivalled firsthand knowledge of Cuba

John Faithfull, Travel Expert

"Personalised service. Seemed to really want to get it right for us. Very impressed when I first called and John spent 40 minutes finding out what we wanted to do and tailoring it for us."

"The expertise that John has really gave us faith in where we were going, the regions, the hotels, the trips. John knew about it all, he described them in detail, and when we asked for different regions he was straight in there with suggestions and ideas. The way the whole trip was planned and presented to us, never any pressure to book or any problem to change plans /ideas."

"John Faithful was wonderfully helpful and conscientious in arranging the itinerary and was always ready to suggest alternatives or rearrange matters without any hesitation; this and his detailed knowledge gave one great confidence."

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For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

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