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Santiago de Cuba, Cuba

Highlights of Eastern Cuba

  • TAILOR-MADE HOLIDAY IDEA

Duration

15 Days

Prices Start from

£4,835 ex. flights

Ideally suited to second time visitors to Cuba, or those who simply wish to travel to lesser-visited locations that reveal an insight in to the Cuban Revolution, this alternative journey idea ventures to the eastern heartland. See the places that witnessed fierce fighting and the snow-balling of Castro’s military campaign, while making time to see sleepy towns with a yesteryear quality and unwind on undeveloped white sand beaches.

Key Highlights of this Itinerary

Museum of Revolution, Havana, Cuba 1

Tour Havana

Join a walking tour of Old Havana, visit the Ballet School and drive a vintage car.

Gibara, Cuba 2

Trek near Gibara

Embark on a full day of trekking in the hills of the Pinares de Mayari.

Sierra Maestra Mountain Range, Cuba 3

The Sierra Maestra

Discover the important hideout of Fidel and Che in the lead up to the Cuban Revolution.

Old Santuago de Cuba, Cuba 4

Santiago de Cuba

Soak up the island’s Afro-Cuban culture and visit the cultural points of interest.

Why we like it

This is a journey through Cuba’s revolutionary past, travelling to places that few visitors to the Caribbean island venture. Since a handful of charters fly east into Holguin, the vast majority of wayfarers make a beeline for the beaches of Guardalavaca – but this itinerary takes you away from the masses and deep into the island’s interior on a revolutionary mission. Including time spent hiking in the Sierra Maestra to see Fidel Castro and Che Guevara’s forested hideout and days revelling in the Afro-Cuban culture and rich music scene of Santiago de Cuba, this diverse trip is highly customisable and can be tailored to your specific interests. It would not be right to exclude Havana on any trip to Cuba, so there will be plenty of time to sip a rum cocktail in one of Hemingway’s favourite watering holes, but as a whole this itinerary ventures beyond the ordinary to an area of Cuba that is suited to intrepid travellers.

Don't forget, we will customise this journey to suit you.

Explore our suggested itinerary

Keys:
Internal Flight
  • Days 1-2
    Havana
  • Day 3
    Havana - Holguin - Gibara
  • Days 4-5
    Gibara
  • Day 6
    Gibara - Sierra Maestra
  • Day 7
    Sierra Maestra
  • Day 8
    Sierra Maestra - Santiago de Cuba
  • Days 9-10
    Santiago de Cuba
  • Day 11
    Santiago de Cuba - Baracoa - Playa Maguana
  • Days 12-13
    Playa Maguana
  • Day 14
    Playa Maguana - Havana
  • Day 15
    Havana
Old Havana, Cuba
Old Havana, Cuba
street sidelined by colorful old buildings in Havana, Cuba
Cuba

Vintage Cars & Ballet Rehearsals in Havana

Weave through the extraordinary time warp of Havana in a genuine 1959 Buick, witnessing the fading grandeur of its Vieja’s colonial architecture and the maze of narrow alleys filled with classic cars that (against all odds) continue to grumble over the cobblestone streets. Walk in the footsteps of Havana’s colonial past while visiting the four plazas of Old Havana – Plaza de Armas, Plaza San Francisco de Asis, Plaza Vieja and Plaza de la Cathedral – in the company of your expert guide who can offer insightful historical context along the way. Some of the world’s best ballet dancers come from the Cuban National Ballet School, the largest in the world, and we can arrange a behind-the-scenes tour and an exclusive viewing of rehearsals.

Downtown Havana, Cuba
Downtown Havana, Cuba
Havana, Cuba
Havana, Cuba

Exclusive Access to the Art Scene

Discover its extraordinary cultural scene, learning about its esteemed art collections and the prominent artists that hold a prominent place in Cuban history, perhaps touring the Roberto Salas Gallery and meeting Roberto himself. As Fidel’s Castro personal photographer, he will explain their relationship and touch on his time behind Vietcong lines as a photographic war correspondent. Have the opportunity to meet with four emerging Cuban artists in their studios, getting behind the façade and interacting with this thriving community. We can adapt the visits depending on your particular interests, but options include photography, sculpture and painting.

Gibara, Cuba
Gibara, Cuba

Explore Gibara

By car and internal flight, travel to the sleepy town of Gibara to see its whitewashed houses topped with red roofs – this place is an undiscovered gem with the largest amount of artists per capita in Cuba. While concerts, theatre performances and exhibitions are in no short supply, it is also the launchpad for trekking, waterfall swimming and birding in the panoramic pine-forested mountains of Pinares de Mayari. Drive with your guide to Cayo Saetia to explore the island that was artificially created in the early 20th century. Fringed by 12 sandy beaches and a coral reef that offers some excellent diving, this is the place to spot a quirky mix of endemic and imported species such as deer, zebras, antelopes, buffalo, ostriches, zebras, antelopes and wild bulls.

Sierra Maestra Mountain Range, Cuba
Sierra Maestra Mountain Range, Cuba

Mountains of Fidel & Che Guevara

Journey to the Sierra Maestra, the tallest mountain range in Cuba and the place where Fidel Castro and his band of brothers, including Che Guevara, hid after they sneaked back from Mexico to plot the 1959 Revolution. Until recently, these mountains have been the reserve of lone climbers, history aficionados and adventurers, but our tailor made options allow for a private journey of discovery. Join a gentle hike through the mountains to reach the hideout, the organising and staging post for the Cuban revolution, and visit the preserved huts where Fidel and Che Guevara led the group of revolutionaries to ultimate victory in the Cuban Revolution. The views and crisp air alone are worth the hike.

Santiago de Cuba, Cuba
Santiago de Cuba, Cuba
Snorkellers, Cuba, Cayo Coco, Cuba
Snorkellers, Cuba, Cayo Coco, Cuba

Afro-Cuban Culture & Beach

Physically closer to Kingston, Jamaica than it is to Havana, Santiago de Cuba is the island’s stronghold of Afro-Cuban culture and is makes a stark contrast to the capital city. Visit Revolution Square, the Moncada Barracks and Casa Diego Velazquez, said to be Cuba’s oldest house. A hot spot for music, you must experience some live traditional music at Santiago’s Casa de la Trova, probably one of the best music houses in Cuba. Conclude the trip with days spent in Playa Maguana, staying in a cottage that overlooks an isolated white sand beach. This is a great area for nature lovers as you can explore the nearby biosphere and UNESCO World Heritage site of Cuchillas del Toa, swim in the nearby rivers or snorkel in the ocean.

Accommodation

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

Gran Hotel Manzana Kempinski £££££

  • Cuba
  • City

Constructed between 1894 and 1917 as the first European style shopping arcade in the country, this handsome building is now a high-end hotel, located in the centre of Havana that faces the Capitolio building and the Gran Theatre.

View Property

Plaza Vieja 1912 £££££

  • Cuba
  • Boutique

This two-bedroom casa particular is on the top floor of an historic building that overlooks Plaza Vieja, in the heart of Old Havana. Lovely and clean and in a very atmospheric setting, it is a great base from which to wander the old town.

View Property

Villa Maguana £££££

  • Cuba
  • Beach and Island Escapes

Located next to 2kms of the white-sand beach of Maguana – possibly the most beautiful in Cuba – sit four cottages, each housing 4 rooms, perfect for boho beach living. This is a great area for nature lovers as you can explore the nearby biosphere and UNESCO World Heritage site of Cuchillas del Toa or swim in the nearby rivers.  

View Property

Let’s chat

Speak to our experts

Our team is waiting to help you tailor a trip that will leave you with stories for a lifetime. Call us on

01285 601 784

Send us an enquiry

Or send us a quick email below and start your next journey.

Call us

John knew the ins and outs of Cuba and was able to answer every question (big and small) that we had. We really feel that we had an off the beaten track experience in this already mysterious country.

Destination: Cuba
Travel Expert: John

A note on price

This Itinerary
Price
From £4,835 Per person

When to travel

Cuba in January

The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.

Cuba in February

The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.

Cuba in March

The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.

Cuba in April

The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.

Cuba in May

From May to July temperatures rise rapidly, and the chance of showers increase. It is the start of the rainy season, but most of the rain generally does not occur until the end of July or August.

Cuba in June

From May to July temperatures rise rapidly, and the chance of showers increase. It is the start of the rainy season, but most of the rain generally does not occur until the end of July or August.

Cuba in July

From May to July temperatures rise rapidly, and the chance of showers increase. It is the start of the rainy season, but most of the rain generally does not occur until the end of July or August.

Cuba in August

Hurricane season runs from August to October. However there are still periods of sunshine in between, and you will find that accommodation is easier to come by with the lower visitor numbers.

Cuba in September

Hurricane season runs from August to October. However there are still periods of sunshine in between, and you will find that accommodation is easier to come by with the lower visitor numbers.

Cuba in October

Hurricane season runs from August to October. However there are still periods of sunshine in between, and you will find that accommodation is easier to come by with the lower visitor numbers.

Cuba in November

The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.

Cuba in December

The dry season in Cuba runs from November to April. This also means that it is peak season, especially over the holiday periods. Accommodation needs to be booked well in advance, as the country’s popularity increases.

Why Choose Steppes?

Our knowledge and expertise sets us apart. So too our curiosity. A curiosity of the world and of you, and your passions. It is this that drives us to create a journey that is really bespoke to you.

Are you ready to discover extraordinary?


Why Steppes

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