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Self-drive eastern Cuba: Havana to the Sierra Maestra

12 days from £1472pp

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Self-drive eastern Cuba: Havana to the Sierra Maestra:
Trip Dossier

If you are adventurous in spirit, the most rewarding way to travel around Cuba is to drive your own hire-car. Take your friends or your family and you will relish the flexibility, and the ability to choose how fast and how far you travel before stopping to enjoy a sight or chat to the locals. This two-week private tour takes you not only to Cuba’s highlights but also to areas less visited by tourists in the eastern half of the country. Your hotels are all pre-booked for you.

Cuba is unique and inspiring; a socialist stronghold, with a rebellious history, colonial splendour in many of the towns, spectacular countryside and a Caribbean heart. Its vibrancy and friendly people will make a lasting impression. Walk round Havana’s historic centre; then drive on to Cuba’s other historic cities, Cienfuegos, Trinidad, Sancti Spíritus and Camagüey. Visit Bayamo and hike in the Sierra Maestra, Castro’s pre-revolution hiding place. Finally, visit Cuba’s second city, Santiago, with a very different vibe from Havana. 

Short itinerary

Holiday itinerary

Day 1

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

Day 2

Guided walking tour of Old Havana. Collect hire car.

Day 3

Drive to Cienfuegos port, and on to colonial Trinidad. 2 nights.

Day 4

At leisure in Trinidad and surrounding area.

Day 5

Drive to Sancti Spíritus. Overnight.

Day 6

Drive to Camagüey. Overnight.

Day 7

Drive to Bayamo, 2 nights.

Day 8

At leisure to explore countryside, or to trek.

Day 9

Drive to Santiago. Drop off car. 2 nights.

Day 10

Walking tour of Santiago.

Day 11

Transfer to Santiago airport and fly to Havana.

Day 12

Transfer to airport for international flight home.

Detailed itinerary

Day 1

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

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

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.


Day 3

Drive to Cienfuegos port, and on to colonial Trinidad. 2 nights.

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.

Cienfuegos and the Bay of Pigs

Day 4

At leisure in Trinidad and surrounding area.

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.

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.

Day 6

Drive to Camagüey. Overnight.

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.

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.

Day 8

At leisure to explore countryside, or to trek.
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.
Hike to Fidel's hideout

Day 9

Drive to Santiago. Drop off car. 2 nights.

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.



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.

Day 11

Transfer to Santiago airport and fly to Havana.
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.
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. 

Essential information

Insurance and documents

Travel insurance is essential. Cuban authorities require visitors to have travel insurance, and specifically for the medical and repatriation element of cover to be from an approved provider. For example, Journey Latin America’s recommended insurance company is Campbell Irvine, and their medical and repatriation cover is handled by International Medical Assistance, who are approved by Cuba. Please check with your insurance company that their provider is similarly approved.

Details of our recommended policy can be found on our Travel Insurance page. 

Fully comprehensive car insurance is included, though there is an excess. Please enquire if you wish to purchase Total Damage Waiver. 

The minimum age for hiring a car in Cuba is 21 years. Insurance and supplements for additional drivers can be paid locally, in Cuban Convertible Pesos. There is a CUC20 fee for picking up your car at the airport (payable locally) and additional fees for dropping off your car in towns where there is no car rental office - please ask us for details. Unlimited mileage is included, but not fuel.


A minimum of 6 scenic road journeys in your self-drive car.


Accommodation on this trip is of a superior quality for Cuba where standards of amenities and service, though  constantly improving, can be erratic. You’ll find well-equipped rooms, private bathroom and air-conditioning in most and some local colour and special features.

In Trinidad you’ll be staying in a Cuban family home. The homestay concept in Cuba is not dissimilar to that of the bed and breakfast in the UK.  The main difference is that in Cuba generally all meals can be taken in the house and the food is generally of a high standard! Often an evening meal is obligatory on the first night but this could well be a sizable lobster. Rooms are rudimentary but homely and comfortable with en suite facilities. The level of interaction can depend on the owners – most have some basic English  ̶  and of course the guests. Most homestays in Trinidad are in a good central location. When we send your final confirmation we'll be able to give you the name of the house in which you'll be staying.


Breakfast daily. Dinner day 3.


We carefully select our local partners; their English-speaking guides understand the expectations of our clients very well, and are consistently singled out for praise by the latter on their return.

Included excursions

• Guided walking tour of Old Havana.
• Guided walking tour of Santiago.

Summary of nights

12 days, 11 nights: Havana 2; Trinidad 2; Sancti Spiritus 1; Camagüey 1; Bayamo 2; Santiago 2;  Havana 1.

Included in the journey price

• Services of our team of experts in our London office.
• Services of Journey Latin America local representatives and guides.
• Self-drive car hire as specified, with insurance.
• Accommodation as specified.
• Meals as specified.
• Excursions as specified, including entrance fees.

Not included in the journey price

• Tips and gratuities.
• Flights to and from the UK.
• Meals other than specified.
• Airport taxes, when not included in the ticket.
• Optional excursions.


The unit of currency in Cuba is the Cuban peso.

Daily spend

It is very difficult to give a guideline for essential expenses but a budget of around £25 per day should cover the cost of meals not included in the holiday itinerary, drinks and the odd souvenir. Eat at the best restaurants and you will pay considerably more.

How to take it

Cuba imposes a 10-15% charge on dollar exchange. To avoid this, you should travel a reasonable quantity of with sterling or euro cash (no more than is covered by your insurance). Notes should be in good condition, soiled or torn ones may be refused. Both euros and sterling are accepted in most banks and some of the larger hotels. You can change these into convertible Cuban pesos (CUC) on arrival. Keep the official receipt from your transaction, because you will need this should you want to change any currency back to sterling or euros at the end of your trip. 

Credit cards (not issued by US banks) are also accepted in some places, but be aware that there is a 11% surcharge on payments made by card, including on cash advances. Havana has a few ATMs and there are a couple more popping up in other cities, although these cannot be relied on. Maestro cards are not accepted in Cuba. 

Travellers’ cheques are another option, though these are gradually falling out of use (in Cuba those drawn on a US bank, eg American Express, will be refused). 

In October 2013 President Castro announced the abolition of the artificial Cuban Convertible Peso, allowing Cubans and visitors to exchange hard currency for ordinary pesos. This change is predicted to be in place by the end of 2014.


Tips are welcomed and local guides often rely on their tip as a significant proportion of their income. 

Most service industry workers will expect a tip of some kind and so it is useful to have spare change for hotel porters, taxi drivers and the like. It is common to leave 10 - 12% in restaurants.

Many Cubans lack what we consider to be daily necessities, such as soap, plasters, bras, aspirin and stationery.
If you have room in your case for some such things, they will be hugely appreciated by the islanders.

Tipping guidelines can be found in our Briefing Dossier.

Airport taxes

If you have purchased your flights through Journey Latin America, the international departure tax is usually included in the ticket.

Departure tax from Cuba is now (as of May 2015) included in  the price of your ticket.

Journey grade

Generally this holiday is suitable for all able, reasonably fit visitors, including families. You should have in your party a confident driver, preferably with some mechanical knowledge.

Road maps and signage are poor, but roads are lined with local people who are happy to help, most speak a little English, though if you speak a bit of Spanish it certainly helps. With a Silva compass and a decent map (we’ll give you one), you can find you’ll get to your destination safely (NB: satnavs don't work properly in Cuba). Main roads are in a relatively decent condition; venture off the beaten track and you will encounter potholes and other barriers requiring caution. The road between Santiago and Baracoa in particular is steep and in poor condition. Since there is no car hire office in Baracoa, you have to give up your car in Santiago.

In Cuba there are often delays and occasionally cancellations – patience and a flexible attitude will be a virtue in these situations.


As Cuba lies in the Caribbean, it has a tropical climate that is split into two seasons, one wet and one dry.

However, Cuba is generally hot throughout the year (18-32°C) with regular rainfall and high humidity. The rainy season runs from May to October and from July to September, humidity can be very high. The east of the island is hotter and more humid that the west. Hurricanes and tropical storms are possible from July to October.

Clothing and special equipment

No special clothing or equipment is required although comfortable walking shoes or trainers, and sandals would be useful. Light, summer clothing will be adequate for these hot temperatures, and the dress code is very casual everywhere. Thin, long-sleeved garments may be useful for evenings, and a lightweight raincoat is the best protection against tropical downpours. We also recommend that you pack a torch as lighting can be poor at night.

Protection against the sun (sunblock, sun hat) and mosquito repellant are essential and you should bring swimwear. A daypack is useful for carrying sunblock, guidebook, water and any extra layers.

We suggest that you provide your own reflective jackets for all passengers, and a first aid kit. Sometimes power cuts and closures mean that usable petrol stations are far apart, so fill up whenever you have the chance.

Please get in touch with the office before departure if you have any doubts. Good equipment is very important and hard to come by in Cuba.


Preventative vaccinations are recommended against the following: typhoid; polio; tetanus; hepatitis A. For specific requirements you must consult your GP.

You can also find helpful information on the Masta Travel Health website. 


Holders of a full British passport do not require a visa, although passports must be valid for at least 6 months after the trip begins. A completed Cuban tourist card is essential for all UK citizens travelling to Cuba, we will organise this for you. Clients with a different nationality should enquire with us or check with the Cuban consulate.

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