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Self-drive eastern Cuba: Havana to the Sierra Maestra

12 days from £1,774pp

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Self-drive eastern Cuba: Havana to the Sierra Maestra


Private Journey


Day 1

Arrive in Havana. Transfer to hotel close to the waterfront in the historic centre.
Malecon in Havana

Private transport to your modern hotel just off the seafront promenade (Malécon) close to the lively historic centre of Havana.

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Malecon in Havana

Day 2

Guided walking tour of Old Havana. Collect hire car.

Your introduction to the city is a guided walking tour of Old Havana. The streets of La Habana Vieja were declared a UNESCO World Heritage Site in 1982, and the subsequent restoration of this part of town has transformed it into arguably Latin America's finest colonial quarter, in marked contrast to the rambling, potholed streets and crumbling façades around it.

Stroll along the cobbles, between grand, pastel-hued mansions and bustling street life. Music seeps out of every doorway and the narrow streets are clogged with gargantuan, crumbling 1950s American cars, which you will have the option of hopping into and cruising down the Malecón. You'll have trouble keeping your camera by your side as iconic images flash before you round each and every corner.

Collect your hire car, a Seat Althea or equivalent.

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Day 3

Drive to Cienfuegos port, and on to colonial Trinidad. 2 nights.
Cienfuegos and the Bay of Pigs

Drive on to the city of Trinidad through the central heartland of Cuba – a transition between the pre-Revolutionary prosperous western plantations and the cattle pasture of the poorer east. Maybe stop off in the elegant city of Cienfuegos, an important port town founded by French settlers from Louisiana in 1819. Its French founders left their mark in broad neoclassical boulevards, art deco façades and blond inhabitants but there’s also a strong Afro-Caribbean presence.

This is a seafaring city with salt in the air; it’s the world’s primary sugar port. The ambience and architectural style is distinct from that of the rest of the island. Continue by car to Trinidad, declared a UNESCO World Heritage Site in 1988. Its popularity has not affected its colonial charm and unhurried atmosphere.  You’ll be staying in a family home here for 2 nights.

There’s a feast of terracotta-tiled roofs, cobbled streets and pastel-coloured buildings. Founded in 1514, the town was originally used as a base for expeditions into the 'New World'; its squares and churches date from the 18th and 19th centuries. The town has hardly changed in a century, no suburbs creep out from its historic centre and no high-rise buildings obscure the view to the sea. Home-grown talent fills the squares and music venues in the evenings, when the town comes alive with dancing and the sound of salsa. Evening entertainment continues into the early hours with dancing and music each night.

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Cienfuegos and the Bay of Pigs

Day 4

At leisure in Trinidad and surrounding area.
Colonial Trinidad de Cuba

At leisure in this fascinating and varied area. Venture into the surrounding countryside, the Valle de los Ingenios (valley of sugar mills). In the 18th and 19th centuries, this region was one of the wealthiest as a result of its participation in the sugar boom. Visit the Manaca-Iznaga tower, climb to the top and enjoy some of the best views in Cuba.

From here, the plantation owner kept a watchful eye on the slaves working in the fields below. The views across the valleys of sugar cane fields are breathtaking in the late afternoon light.

You might drive up to Topes de Collantes National Park.  The park is in the Escambray mountains which are a backdrop to Trinidad and have an exquisite landscape of forests, waterfalls, deep valleys and lakes, perfect for car touring or hiking along visible trails.

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Colonial Trinidad de Cuba

Day 5

Drive to Sancti Spíritus. Overnight.

Drive to Sancti Spíritus. This city sits right slap bang in the centre of Cuba. It was one of the original 7 Cuban cities founded by the Spanish in 1514. Its colonial origins are evident in its buildings and layout, although it is not as exquisite and well preserved as the Trinidad to the south, which as a result attracts more visitors. Its neglect by governments through the ages adds to its charm for some.

Highlights include the green-towered Parroquial Mayor, the country's oldest (founded in the early 16th century). It’s close to town's main square. Another top attraction in this central area is the Museo de Arte Colonial (Colonial Art Museum), occupying one of Sancti Spíritus's loveliest colonial homes. The luxurious mansion belonged to one of one of Cuba's old aristocratic families. Following their flight from Cuba after the Castro Revolution, it became the property of the state in 1961. Most of what you see inside, from furniture to paintings, is original.  The town also hosts one of Cuba's older river bridges. Graced with five arches, this short bridge was constructed in 1815 from clay bricks, designed for pedestrians and carriages during colonial times, and it remains closed to modern traffic. Overnight.

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Day 6

Drive to Camagüey. Overnight.
Camaguey House

Drive to Camagüey. Founded by Spanish conquistadors in the 16th century, the city, with its winding streets, is in marked contrast to the grid system which characterises the majority of Cuban towns. Stately colonial houses facing onto streets; huge windows protected by wrought-iron grilles; lush green gardens tucked behind the walls.

It's a vibrant place bursting with culture - national poet Nicolás Guillén was born here and the Camagüey Ballet is internationally renowned. On Saturday nights, there is a lively street party along its main thoroughfare, Avenida República. Overnight.

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Camaguey House

Day 7

Drive to Bayamo, 2 nights.

Drive to Bayamo, the capital of the Granma province and rich in history and nature. Low-key Bayamo is renowned as containing almost half of the most significant historical sites in the country. A stroll round of this city will help you discover some of the most significant sites, view the cathedral, spectacular colonial architecture, and enjoy the elegant houses and plazas.  2 nights.

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Day 8

At leisure to explore countryside, or to trek.
Hike to Fidel's hideout
At leisure. You may wish to arrange a hike into the Sierra Maestra National Park. A popular choice – if you are reasonably fit  ̶  is the walk to Comandancia de la Plata, Castro’s pre-revolution mountain base.
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Hike to Fidel's hideout

Day 9

Drive to Santiago. Drop off car. 2 nights.
Santiago de Cuba

Drive to Santiago de Cuba, the island's most Caribbean city and a melting pot of Haitian, African and Spanish influences, reflected in both its architecture and people. Cuba's second largest metropolis sits in a valley surrounded by mountains huddled around a natural harbour.

Despite being a bustling hive of activity, Santiago retains an intimate and friendly air, more associated with a smaller provincial city.  What's more, the city is jam-packed with culture and tradition, from the deep-rooted African religion of Santería to its conveyor belt of great contemporary musicians.

Hand back your car at the car-hire office. Spend 2 nights here.



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Santiago de Cuba

Day 10

Walking tour of Santiago.
Walking tour of the city. Santiago de Cuba is a city rich in history, art, culture, music and historical sites. Known as the Heroic City, it played an important role at the beginning of the wars for independence. This walking tour takes you along the beautiful city streets and to places of interest, including the Moncada barracks, famed for the unsuccessful attack by Castro’s rebels.  Later, cross by boat to Cayo Granma for lunch, followed by time at leisure in the city.
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Day 11

Transfer to Santiago airport and fly to Havana.
cuba cars
Upon arrival at Havana airport, you'll be escorted to your hotel and have the chance for another look around the capital and to choose somewhere for your final dinner before spending your last night in Cuba.
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cuba cars

Day 12

Transfer to airport for international flight home.

Fly home or continue to spend a few days on a Cuban Caribbean beach. 

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About Private Journeys

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