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Self-drive Cuba: Explore the east

Trips to Tailor

13 days from £2,280

per person
Based on two people sharing & excluding flights
Relish the flexibility and decide how quickly you travel in a self-drive hire car, visiting less-visited but historically significant eastern side of Cuba. Hotels and some city tours are pre-booked.
What to expect
Itinerary

Explore the tour day by day, from the highlights to the quieter moments in between. Here’s how each day unfolds and what to expect along the way.

Day 1 - Havana
Transfer from the airport to your hotel in Havana.

Your accommodation is in the very heart of historic Havana just a quick stroll from the city’s principal squares.

Hostel Madero

Madero Bed and Breakfast is one of a new generation of small Cuban properties which are considerably more upmarket, contemporary and stylish than the traditional homestay.

This popular and well-regarded choice is in the heart of historic Havana, just a quick stroll from the city’s principal squares. The six guest rooms and one larger suite with a balcony are distributed over three floors, all tastefully furnished in modern muted colours and pale wood with up-to-date private bathrooms.

You are welcome to make use of a spacious living room and kitchen on the ground floor and there is a rooftop terrace with comfy armchairs. The property is also known as Hostal Madero, but it is certainly much better appointed than what we would normally expect from a hostel, with excellent service from helpful, mainly English-speaking staff.

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 classic 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.

Hostel Madero

Madero Bed and Breakfast is one of a new generation of small Cuban properties which are considerably more upmarket, contemporary and stylish than the traditional homestay.

This popular and well-regarded choice is in the heart of historic Havana, just a quick stroll from the city’s principal squares. The six guest rooms and one larger suite with a balcony are distributed over three floors, all tastefully furnished in modern muted colours and pale wood with up-to-date private bathrooms.

You are welcome to make use of a spacious living room and kitchen on the ground floor and there is a rooftop terrace with comfy armchairs. The property is also known as Hostal Madero, but it is certainly much better appointed than what we would normally expect from a hostel, with excellent service from helpful, mainly English-speaking staff.

Day 3 - Cienfuegos
Drive to Cienfuegos port, and on to colonial Trinidad.

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.

This attractive, extensively restored colonial hotel is set a short walk from the heart of Trinidad, near the lively Parque Cespedes. There is a central patio which all 40 rooms surround. Rooms are spacious and equipped with air-conditioning, TV, minibar and en suite bathroom. Many also have a balcony or terrace, with some having pleasant vistas of the park and others with no view to speak of, but which tend to be quieter. Facilities include a public restaurant, lobby bar and small shop. There is free parking available on the street in front of the property.

Day 4 - Trinidad
Walking tour of Trinidad and optional trips out into surrounding countryside.

On your guided tour you will wander through Trinidad’s cobbled streets and elegantly crumbling town houses which lead to vibrant plazas frequently filled with music and salsa dancing. As you visit the Plaza Mayor and Museo Romántico, you’ll be introduced to the history of this UNESCO World Heritage Site, which seems barely touched by the modern world. Stop at an authentic Cuban bar to sample a traditional cocktail, before heading off to one of Trinidad’s ceramics workshops.

Before or after the tour you may 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. The Manaca-Iznaga tower has some of the best views in Cuba. From there, the plantation owner kept a watchful eye on the slaves working in the fields below. Or 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.

Panoramic view over the city of Trinidad, Cuba with mountains in the background and a blue sky. The bell tower belongs to the Iglesia y Convento de San Francisco.

This attractive, extensively restored colonial hotel is set a short walk from the heart of Trinidad, near the lively Parque Cespedes. There is a central patio which all 40 rooms surround. Rooms are spacious and equipped with air-conditioning, TV, minibar and en suite bathroom. Many also have a balcony or terrace, with some having pleasant vistas of the park and others with no view to speak of, but which tend to be quieter. Facilities include a public restaurant, lobby bar and small shop. There is free parking available on the street in front of the property.

Day 5 - Sancti Spiritus
Drive to Camagüey via Sancti Spíritus.

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 in certain areas have led to many of the buildings taking on an authentic faded charm.

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.

Continue to Camagüey.

This two-storey, sugar-pink property occupying a colonial-era residence is probably the closest that Cuba gets to a boutique style hotel. Opened in late 2011, it is simply furnished, with just ten large rooms featuring good bathrooms overlooking a central patio. Befitting its name, which means ‘railroad’, the hotel is dotted with art featuring trains and railways. It has a pleasing location in the historical centre of Camaguey, just one block from the main square. A decent breakfast is served and the staff have frequently been praised by guests for their friendliness, helpful attitude and sunny disposition.

Day 6 - Camaguey
Guided walking tour of 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.

On your guided walking tour you will discover its irregular, intricate street network while admiring public and private buildings of great colonial architectural beauty, including Plaza San Juan de Dios.

Old vintage car on the street, Camagüey Cuba

This two-storey, sugar-pink property occupying a colonial-era residence is probably the closest that Cuba gets to a boutique style hotel. Opened in late 2011, it is simply furnished, with just ten large rooms featuring good bathrooms overlooking a central patio. Befitting its name, which means ‘railroad’, the hotel is dotted with art featuring trains and railways. It has a pleasing location in the historical centre of Camaguey, just one block from the main square. A decent breakfast is served and the staff have frequently been praised by guests for their friendliness, helpful attitude and sunny disposition.

Day 7 - Santiago de Cuba
Drive from Camaguey to Santiago de Cuba

Take the Carratera Central to Autopista Nacional (A1). We recommend a short stop at Bayamo, a gem featuring pastel painted houses and marking the spot where the mountains of the Sierra Maestra begin. (If you are interested in trekking we can arrange an additional night or two so you can visit the Comandancia de la Plata. This was Fidel’s mountain hideout, where his revolutionary strategy was organised). Alternatively, just have a leisurely stroll around the streets and square before continuing via Juiguani to Santiago de Cuba. With a stop planned, leave early and allow a full day.

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.

Hotel Casa Granda

This classic hotel makes much of its history, and justly so – constructed in 1914, the property has attracted some illustrious guests in its heyday including movie stars, jazz singers, author Graham Greene (who wrote the classic novel Our Man in Havana) and baseball great Babe Ruth. It’s an imposing building, inspired by the colonial edifices of the Spanish era with graceful arches and shady terraces.

The guest rooms are located on five floors, some with views of the main square on which it has pride of place. A great location as a base for explorations, it sits in the very heart of an exuberant and musical city.

Other facilities include a large airy restaurant and a wonderful rooftop garden with cocktail  bar and good views over the city and the sea.

Day 8
Guided walking tour of Santiago.

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.

Also known as the Heroic City, Santiago played an important role at the beginning of the wars for independence. This guided tour takes you to the major places of interest, including the Moncada Barracks, famed for the unsuccessful pre-revolution attack by a handful of rebels led by Castro. This failed attack nevertheless was the springboard which launched the revolution. Cementerio Santa Ifigenia, Barrita de Ron Caney, the Casa del Habano and the San Pedro de la Roca colonial fortress. You’ll have a seafood lunch at the quay.

Hotel Casa Granda

This classic hotel makes much of its history, and justly so – constructed in 1914, the property has attracted some illustrious guests in its heyday including movie stars, jazz singers, author Graham Greene (who wrote the classic novel Our Man in Havana) and baseball great Babe Ruth. It’s an imposing building, inspired by the colonial edifices of the Spanish era with graceful arches and shady terraces.

The guest rooms are located on five floors, some with views of the main square on which it has pride of place. A great location as a base for explorations, it sits in the very heart of an exuberant and musical city.

Other facilities include a large airy restaurant and a wonderful rooftop garden with cocktail  bar and good views over the city and the sea.

Day 9 - Gibara
Drive from Santiago to Gibara.

Head north cross country towards the Caribbean coast. You will arrive at the region’s major town Holguin ( 3-4 hours) from where it’s a drive of a further hour to Gibara. Holguin is Cuba’s fourth largest metropolis but for visitors is primarily a transit point for those heading to the island’s increasingly popular north-east coast beaches such as the resort of Guardalavaca, 50km away. Despite its size, Holguín is an easy-going and friendly city. The centre is quite dilapidated but its several parks and squares are dominated by statues to national heroes.

The off-the-beaten-track community Gibara, a little port situated on a bay on the scalloped north east coast has been spruced up after earthquake damage, is delightful and worth the detour. The fishing port is situated in rugged, hilly landscape dotted with royal palms and interspersed with sugar cane plantations in the valleys.

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Hotel Ordono

Gibara is the epitome of a remote one-horse town, a folksy and recently renovated fishing port on the coast near Holguin which is the perfect host for its blossoming film and arts festivals. The boutique-style Hotel Ordoño, a former Spanish colonial residence which has been delicately and sensitively restored, is a response to the growing interest in the town among visitors to Cuba. The exterior and some of the stained glass features (typical of Gibara’s architecture), including an impressive atrium, are ornate but the air-conditioned guest rooms are decorated with contemporary simplicity and have a light and airy feel. Each of these rooms and suites has individual character and painted murals in the bathrooms. There’s a two-floored roof terrace where you can take the sun, and an à la carte restaurant (but no lift). Service is reputedly friendly and helpful.

Day 10
At leisure in Gibara.

The crinkly coastline, with secret coves which once sheltered buccaneers, is gradually being opened up to tourism, but the port Gibara retains its off-beat, remote ambiance. The town is named after the lumpy hill which composes its backdrop. There’s a grand view of the town from the ruined fort El Cuartelon. The main square, dominated by a 19th century cathedral built in eclectic mix of styles, is shaded by African oak trees imported from Angola in the 1970s. The calm little streets and waterside malecón are lined with sedate old houses with porches and stained glass windows, gradually being done up.

You may decide to drive or walk further afield to visit the Cavernas de Panadernos, a chain of underground limestone caves – you are advised to take a local guide if planning to enter them; you can hire one in town. The presence of fluttering bats ads to the eerie atmosphere. Alternatively drive along the craggy coast to one of the gorgeous beaches, many of which now feature hotels and facilities. Guardalavaca is the best established of these.

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Hotel Ordono

Gibara is the epitome of a remote one-horse town, a folksy and recently renovated fishing port on the coast near Holguin which is the perfect host for its blossoming film and arts festivals. The boutique-style Hotel Ordoño, a former Spanish colonial residence which has been delicately and sensitively restored, is a response to the growing interest in the town among visitors to Cuba. The exterior and some of the stained glass features (typical of Gibara’s architecture), including an impressive atrium, are ornate but the air-conditioned guest rooms are decorated with contemporary simplicity and have a light and airy feel. Each of these rooms and suites has individual character and painted murals in the bathrooms. There’s a two-floored roof terrace where you can take the sun, and an à la carte restaurant (but no lift). Service is reputedly friendly and helpful.

Day 11 - Santa Clara
Drive back west to Santa Clara.

Head back to the Carretera Central via Holguin and westward to Santa Clara. (The northern route – the Circuito Norte – is not currently recommended, as the road surface is poor in places and facilities such as petrol stations and eateries are rudimentary). This is a very long day so we suggest an early departure, allowing a good couple of hours during daylight for stops and lunch.

Che Guevara memorial
Hotel Central Santa Clara

One of the landmark buildings in Santa Clara, overlooking the main square Parque Vidal, has opened after years of renovation. Hotel Central houses 26 guest rooms in a prime location; with its graceful colonial-style colonnades and balconies it is without a doubt one of the prettiest buildings in Santa Clara.

After decades of disrepair the hotel has been restored to its 1929 glory, maintaining intact its original ornate façade, and the ample lobby showcasing the grand marble stairs. The guest rooms have high ceilings and doors maintaining the original character. Overall though it’s a mix of the nostalgic with the contemporary. There is a lobby bar and a terrace bar on the third floor which is a great spot to enjoy many beautiful tropical evenings enjoying the breeze from the square, sipping ‘mojitos’ and listening to great Cuban music.

Day 12
Drive from Santa Clara back to Havana.

We suggest you take the route A1 straight back to Havana as this will allow you time to look around Santa Clara before you leave. Santa Clara, founded on agriculture and mining, gained importance when a railway was built to connect the city with Havana. This track provided for one of the most momentous events in Castro’s revolutionary campaign: the hijacking of a train carrying government guns and soldiers. A few of the carriages are on display in what is this lively university city’s most important monument.

If you enjoy life on the road you can opt to travel via Matanzas, a city dating back to the 17th century which founded its prosperity on the commerce from its sugar mills and from the accessibility provided by the 19trh century railway connecting it with Havana. Indeed, for a while it was second only to Havana in importance. Matanzas became known as the Athens of Cuba, referring to its intellectual and artistic prowess, with flourishing theatres and libraries. Even more important to its identity is its role as the place where the famous rumba dance was invented, and music permeates every comer of this otherwise quiet city.

Hostel Madero

Madero Bed and Breakfast is one of a new generation of small Cuban properties which are considerably more upmarket, contemporary and stylish than the traditional homestay.

This popular and well-regarded choice is in the heart of historic Havana, just a quick stroll from the city’s principal squares. The six guest rooms and one larger suite with a balcony are distributed over three floors, all tastefully furnished in modern muted colours and pale wood with up-to-date private bathrooms.

You are welcome to make use of a spacious living room and kitchen on the ground floor and there is a rooftop terrace with comfy armchairs. The property is also known as Hostal Madero, but it is certainly much better appointed than what we would normally expect from a hostel, with excellent service from helpful, mainly English-speaking staff.

Day 13 - Havana
Drop off your car and transfer to the airport.

Drop off your hire car at the car rental agency and proceed to the airport for your international flight, or continue with any tailor-made extension you have booked with us.

Self-drive Cuba: Explore the east full itinerary
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Overview
Places Visited

The places you’ll stay and explore on this tour. Here’s a closer look at each one and what makes it worth the trip.

Havana holidays showcase one of the world’s most captivating cities, where grand colonial squares, colourful classic cars and faded mansions create an unforgettable atmosphere. As Cuba’s cultural and historic heart, Havana blends architecture, music and everyday life in a way few destinations can match.

Havana

Discover a fascinating region at the heart of Cuba, where elegant colonial architecture, revolutionary history and one of the Caribbean’s most infamous shorelines combine to create an unforgettable journey. Our Cienfuegos holidays take in the French-inspired streets of Cienfuegos, the revolutionary landmarks of Santa Clara and the historic Bay of Pigs.

Cienfuegos, Santa Clara and Bay of Pigs

Trinidad holidays offer a captivating mix of colonial history, music and natural beauty. Wander UNESCO-listed cobbled streets, soak up the city’s vibrant atmosphere and explore the waterfalls, forests and jade-green pools of nearby Topes de Collantes.

Trinidad and the Escambray Mountains

Santiago de Cuba holidays offer a fascinating blend of revolutionary history, Afro-Cuban heritage and Caribbean culture. Set between the Sierra Maestra mountains and the Caribbean Sea, Cuba’s second city is renowned for its music, festivals and the events that helped shape the island’s history.

Santiago de Cuba
Overview
Highlights

This holiday takes you not only to Cuba’s highlights but also to areas less visited by tourists in the eastern half of the country. If you are adventurous in spirit, the most rewarding way to travel around Cuba is to drive your own hire-car. 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. 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 eastern region of the country and back, visiting Cuba’s other historic cities: Cienfuegos, Trinidad, Sancti Spíritus, Camagüey, Santiago and Santa Clara. Drive through the wild mountains of Sierra Maestra, Castro’s pre-revolution hiding place, and continue to the Caribbean coast, basing yourself at the unassuming little fishing port Gibara to explore the attractive wooded bays and glittering beaches of the unspoilt northeastern littoral.

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Chris Rendell-Dunn

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What you need to know
Essentials

The practical detail for this tour, all in one place. Transport, accommodation, what’s included and what to pack, so you know exactly what to expect before you go.

Cuba information
What's included in the 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
Taxes and compulsory charges
Included Excursions
Guided walking tour of Old Havana
Guided walking tour of colonial Trinidad
Guided walking tour of Camaguey
Guided panoramic tour of Santiago
11 days of self-drive around Cuba
What's not included in the price
Tips and gratuities
Flights to and from the UK
Meals other than specified
Airport taxes, when not included in the ticket
Optional excursions
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Things to do

We proudly offer the widest range of activities, excursions and one-of-a-kind experiences across all our destinations, tried and tested personally by our travel experts.

Explore the cobbled streets of colonial Trinidad. You might extend the trip with an optional tour of the old sugar mills in the surrounding Valle de los Ingenios.

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Visit Trinidad’s Casa de la Trova to feel the rhythm that fuels Cuban life.

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Situated in the heart of Cuba, Santa Clara is a vibrant city steeped in history as a result of its involvement in the battles which took place during the Cuban Revolution. Che Guevara is especially venerated here, the site of his Mausoleum. In 1967 Guevara and a couple of dozen of his Cuban comrades were…

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Accommodation

Browse our unrivalled portfolio of accommodation. Every option has been carefully chosen by our team of travel experts, so you can rest assured that you will relax in utter comfort

This two-storey, sugar-pink property occupying a colonial-era residence is probably the closest that Cuba gets to a boutique style hotel.

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The Iberostar Grand Hotel Trinidad is an elegant, restored colonial property, with an impressive marble staircase, cigar bar and beautifully decorated rooms.

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Hotel Casa Granda is an imposing, classic property dominating the main square of Santiago de Cuba.  

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Level definitions

Essential
What it means

Stay in comfortable, well-located hotels chosen to keep you close to the action. These are reliable, practical places with everything you need for a good night’s sleep, sometimes a smaller or family-run find, sometimes a larger, more functional hotel. It’s a straightforward style of stay that keeps costs down and leaves more of your budget for the experiences themselves.

Premium
What it means

Return each evening to well-appointed hotels chosen for their comfort and setting. Rooms are spacious and properly equipped, with all the mod cons you’d expect, and facilities to include a restaurant, a bar or lounge, and often a pool or spa to unwind in. It’s an easy, comfortable style of travel, with somewhere relaxed to look forward to each day.

Essential
What it means

Settle into stylish hotels picked for their character, setting and service. That might be a luxurious city hotel like the Loi Suites in Buenos Aires, or somewhere with a setting you won’t forget, a former estancia on the Patagonian steppe or a lodge at the foot of Machu Picchu. This is our most memorable style, where the hotel becomes part of the journey itself.

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