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The rooftops of Baracoa among palms, with the flat-topped mountain of El Yunque beneath the clouds beyond

Sample journey · 10–12 days

Cuba's Oriente: the home of son, the Sierra Maestra and Baracoa

Havana, Santiago de Cuba, the Sierra Maestra, Bayamo, Baracoa & Holguín

Photo: Will Jephcott / Unsplash

Illustrative journey ideas — not bookable packages. No prices, dates or accommodation are implied.

The Oriente, as Cubans call the east of the island, is far from Havana in more than kilometres. The country is mountainous, the Afro-Caribbean and Haitian roots run deeper, and the music sounds different: Santiago de Cuba is the birthplace of son, from which salsa later grew. In the forests of the Sierra Maestra the guerrilla camp still stands, and beyond the mountains, where for a long time no road ran, lies Baracoa, the oldest Spanish town on the island, ringed by rivers, cacao plantations and palms.

This is a journey for experienced travellers who want to understand, not just to see. The drives are long, comforts are simple and daily life in Cuba is hard right now, especially in the east, which recent hurricanes have also hit badly. So before any journey we look at the current situation and travel advice together with you, and shape the route around what is genuinely possible at the time.

The route

The journey

  1. Havana
  2. Santiago de Cuba
  3. Sierra Maestra
  4. Bayamo
  5. Baracoa
  6. Holguín
  1. A view through an arched balcony doorway over the rooftops of Havana

    01Days 1–2 · Havana

    A short opening chord

    After the long flight, a night in Havana and one slow day: a morning walk through the squares of Old Havana with a local guide, lunch at a family-run paladar and an evening on the Malecón. It's enough to catch the capital's rhythm, and to have something to compare the east with.

  2. A hilly street of weathered, colourful houses in Santiago de Cuba, running down towards the bay

    02Days 3–5 · Santiago de Cuba

    The city where son was born

    The domestic flight east takes about two hours. Santiago is hot, hilly and loud: in the evenings son groups play in the hall and courtyards of the Casa de la Trova, and the Tivolí quarter carries a Haitian and French heritage. At the mouth of the bay the El Morro fortress stands on its rock, a UNESCO World Heritage site, and in the hills beyond the city is the basilica of El Cobre, Cuba's most revered shrine.

  3. A horse-drawn cart on a tree-lined country road in Santiago de Cuba province, seen through a car windscreen

    03Days 6–8 · The Sierra Maestra & Bayamo

    A forest trail to a mountain camp

    About three and a half hours west to the village of Santo Domingo, by a river at the foot of the mountains. The next morning, a 4×4 up a steep road, then on foot with an obligatory local guide for around three kilometres along a forest trail to the Comandancia de la Plata, the 1958 guerrilla headquarters whose wooden huts still hide beneath the trees. The trail is steep and slippery in places, so moderate fitness is needed. Afterwards, a night in Bayamo, where Cuba's national anthem was first sung in 1868 and horse-drawn carts still clatter through the streets.

  4. A dry hillside of grass and scrub above an empty road near Guantánamo

    04Days 9–10 · La Farola & Baracoa

    Over the mountains to the oldest town

    The longest day of the journey: through Santiago and Guantánamo along the south coast, then the La Farola road looping over the mountains to Baracoa, about seven hours in all. Before this road was built, the town was reached mostly by sea, and you still feel it: Baracoa is distinct, slow and welcoming. Cacao and coconuts grow here, and the local cooking is unlike the rest of the island's: try fish in coconut sauce and cucurucho, a sweet wrapped in a palm-leaf cone.

  5. A calm river between green banks near Baracoa, with forested hills in the distance

    05Days 11–12 · Baracoa & Holguín

    Rivers, El Yunque and a cacao farm

    One morning, a hike up El Yunque, the flat-topped mountain above town: the trail through forest and across rivers takes a few hours, and from the top, clouds permitting, you can see the whole coast. Another day, by boat on the Toa or Yumurí river between walls of rock, a visit to a family cacao farm to see how beans become chocolate, and a swim at Playa Maguana. To leave, along the north coast to Holguín, around five hours by road, and the flight home via Havana or direct.

Experience highlights

  1. 01

    An evening at the Casa de la Trova

    Son where it was born, without stage gloss, among local dancers.

  2. 02

    The Comandancia de la Plata

    A forest trail to the mountain camp where Cuban history was written.

  3. 03

    The La Farola road

    Loops over the mountains to a town long reachable only by sea.

  4. 04

    Baracoa's cacao

    A family farm, chocolate from the bean and cooking you won't find elsewhere on the island.

First, we listen. Then, we explore what's possible.

Make it your own

  • With the west

    Begin with more time in Havana and the Viñales Valley, stretching the journey to two weeks and spanning the whole island.

  • More active

    A multi-day trek through the Sierra Maestra with a night in the mountains, if permits and the situation at the time allow.

  • With the coast

    End with a few days by the sea on the Holguín coast before flying home.

  • More music

    Santiago holds its carnival in July, and all year round there are dance lessons and meetings with local musicians.

Practical considerations

  • Day-to-day conditions in Cuba have been changing quickly: there are long power cuts and shortages of fuel, food and some goods, and the eastern provinces were badly damaged by hurricanes recently. So we always check the latest situation and official travel advice before planning, and again before travel.
  • Domestic flights and long drives can change or run late, so the route keeps time in hand, and the last night before the flight home is planned close to the airport.
  • Cash still matters a great deal, and foreign bank cards don't work everywhere; it's worth talking through how best to handle money before you go.
  • The dry season, roughly November to April, is usually the most comfortable; June to November is hurricane season, and the Baracoa area is wetter than the rest of the island.

General guidance only. Seasons, weather and wildlife are never guaranteed, and travel requirements are always worth checking before you go.

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