We will set off in classic 1950s American cars to get an overview of the city before exploring the Old Town on foot. We’ll visit the well-to-do 1950s Miramar district, home to some of Havana’s most striking 20th century architecture. Keep an eye out for the imposing Russian embassy and the elegant neoclassical homes, many of which are now embassies. We will drive through the beautiful residential district of Vedado where wealthy sugar barons built elegant mansions in the early 20th century and stop in Revolution Square where Fidel made his famous speeches. Driving back along the picturesque coast road (the Malecon), the classic cars will drop us off in the Old Town where we will continue on foot, exploring the four original squares around which the city was founded. After lunch (included) free time to explore at your own pace.

We leave Havana and drive east to Santa Clara, the site of the last battle of the Cuban Revolution. In December 1958, Che Guevara and his troops ambushed an armoured train carrying arms to Santiago de Cuba and this was a major turning point in the Revolution. We visit the train museum and the Mausoleum of Che Guevara and his comrades who died in Bolivia. The museum attached to the Mausoleum has many of his former belongings and provides a fascinating insight into one of the 20th Century’s most revered icons. There will be time for lunch in Santa Clara after which we continue to Sancti Spiritus for the night. Sancti Spiritus is a charming provincial town and one of the original 7 settlements founded by the Conquistadors in the 16th Century.

Today is a long driving day as we head to Gibara in the east of the island. We pass through agricultural towns and sugar cane plantations, learning about the importance of sugar in Cuba’s history. We stop for lunch in Camaguey, Cuba’s fourth largest city, to break up the journey. From Camaguey we continue our journey to the East or “Oriente” and arrive late afternoon in Gibara, a sleepy fishing town famous for its Film Festival.

After breakfast we leave Gibara and drive to Birán, tucked inland and birthplace of Fidel Castro, the founding father of the Cuban Revolution. We visit the family homestead where he was born and where his family owned a sugar plantation. It’s an opportunity to learn about how Cuba’s history has always been linked to sugar and the slave trade. Fidel Castro rejected his privileged upbringing to bring about social change in a country of huge extremes of wealth and poverty. After the visit we continue on to Cayo Saetia, an island off the coast of Cuba connected to the mainland by a causeway. Cayo Saetia was formerly a game reserve and became a favoured spot with Revolutionary Leaders for snorkeling and relaxation. The lodge has been converted into a small hotel. Time for late lunch and an afternoon at the beach.

Morning drive towards Baracoa, stopping at the Alejandro Humboldt National Park which is a natural UNESCO World Heritage Site for a walk. We have lunch in Playa Maguana and continue to our destination – Baracoa. Founded in 1512, Baracoa was the first Spanish settlement and served as the capital for three years. It’s location on the easternmost tip of the island left it open to attacks from pirates, smugglers and the English, so three forts were constructed in the 18th Century for protection. Baracoa has only been accessible by road since the 1960s and this has left it largely off the tourist route. Surrounding the quaint town are lush, tropical mountains and golden sandy beaches. This area is renowned for cocoa growing and chocolate production. The Malecon on the northeast side of the town is known as the Caribbean’s first ocean drive. There is still a strong Indian influence here and the El Yunque Mountain, (the anvil shaped mountain described by Christopher Columbus in his diaries) used to be the site of various aboriginal communities. We arrive late afternoon and spend some time exploring before checking into our hotel.

This morning we take a boat trip on the River Toa followed by a short walk through the lush vegetation surrounding Baracoa. The whole area is a Biosphere Reserve and protects the richest endemic flora and fauna in Cuba. The afternoon is free to explore the town or visit the beach.

After breakfast we depart sleepy Baracoa for Santiago de Cuba, known as the ‘city of heroes’ owing to the important role it played in Independence and Revolutionary struggles. Santiago rivals Havana in literature, music and politics, and is rich in traditions, folklore and legends making almost every street corner in the city famous. On arrival visit El Morro Castle, then take an evening walking tour of the colonial heart of the city.

Explore Santiago de Cuba, visiting the Santa Ifigenia cemetery (where Fidel Castro is buried) and the Moncada Barracks. The opening shots of the revolution were fired at the barracks on 26 July 1953 when Castro and his men attacked them. Time for lunch in Santiago before we leave the city behind and drive west towards the green mountains of the Sierra Maestra. We will stop on the way to visit El Cobre, the most sacred pilgrimage site in Cuba. Arrival in the early evening at Villa Santo Domingo for overnight.

We spend this morning in the Gran Parque Nacional Sierra Maestra, a spectacular national park within Cuba’s highest mountain range. This region is well known as Fidel Castro’s base of operations during the Cuban Revolutionary War. High in the Sierra is Comandancia La Plata, the secret mountain hideout from which Castro and Che Guevara planned the revolutionary war in the 1950s. It was also the location for Radio Rebelde which broadcast information for the revolutionaries. We will hike to the revolutionary base and then may have time to bathe in the Yara River. After time for lunch in Villa Santo Domingo, we continue our journey to Camagüey where we’ll spend the night. After almost continuous attacks from pirates, the original city (founded as Santa Maria del Puerto del Principe around 1515 on the northern coast) was moved inland in 1528. The new city was built with a confusing lay-out of winding alleys that made it easier to defend from raiders.

This morning there will be time to explore this historic city, characterised more recently by ‘tinajones’ – large, earthen jugs found in the squares, churches and gardens. They were originally used to store water during drought periods. We will then travel on to Trinidad which was awarded UNESCO World Heritage Site in 1988 and is perhaps the best-preserved colonial town on the island. Exploring Trinidad is like stepping back in time, the cobbled streets and horse drawn transportation whisk you back to colonial times. There are many interesting museums housed in old colonial buildings to visit in the daytime, but it is as the sun sets that Trinidad really comes to life. We recommend a visit to Casa de la Trova for traditional Cuban music and dancing!

Today is a free day to enjoy a number of activities at your leisure, for example horse riding, salsa classes, trekking in the Sierra del Escambray, or a trip on a catamaran out to one of the keys offshore. Trinidad’s small scale makes it easy to explore independently and the many cafes, museums and shops are perfect for browsing and whiling away an afternoon. Ancon beach, a classic Caribbean beach is well worth visiting and easy to reach by taxi. Lunch and dinner today aren’t included but there are plenty of choices to choose from in town or you can eat at your casa.

Today we head for the Bay of Pigs stopping on the way to visit Cienfuegos. This city is known amongst Cubans as ‘The Pearl of the South’ and its colonial centre was named a UNESCO World Heritage site in 2005. Cienfuegos is the only city in Cuba founded by French migrants fleeing the slave revolution in Haiti in the early 19th century. After a morning visit to Cienfuegos we continue our journey and stop for lunch and a swim at Caleta Buena, a natural protected sea-pool. The drive back to Havana takes us first along the Bay of Pigs where the road clings to the coast giving us views of the emerald Caribbean Sea. Upon arrival in Havana we check into our accommodation for the night.

Free day in Havana. You could visit the Museum of the Revolution, housed in an impressive building that was Presidential Palace from 1920 to 1965. The displays cover Cuban history from the Republic to present day with detailed exhibits on the Revolution. In the grounds is ‘Granma’, the yacht used by Fidel and his revolutionaries to sail from Mexico to Cuba in 1956. Just behind the Museum of the Revolution is the Cuban Fine Arts Museum (Bellas Artes), that has a beautiful collection of Cuban art dating from the 19th century to the present day. You can also visit the museum of Hemingway in San Francisco de Paula town at the south of the city. This museum is set in a beautiful property that was Hemingway´s house in Cuba from 1939 until he died in 1961. The house has been kept intact, with all of Hemingway´s belongings left where they were. If you are interested in souvenirs, you can visit the largest handicraft market known as Almacenes San Jose on the port in Old Havana.

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Optional day trip to Viñales. The Viñales Valley is both a National Park and a sixth Cuban UNESCO World Heritage site. The valley is filled with palm trees and small family farms where traditional farming methods are still used cultivate the fertile red soil: oxen can be seen ploughing the fields and palm fronds are used as thatching for houses and barns. The scenery is some of the most impressive in Cuba as huge limestone karsts (sheer-sided, flat-topped hills) rise from the valley floor, riddled with caves and covered in forest. The valley’s microclimate is perfect for growing tobacco; the leaves are dried in thatched barns and used to make Cuba’s world-famous cigars.

In the evening there is an optional trip to the famous Tropicana Nightclub in Havana.

The morning is free for last minute sight seeing or shopping. Check out of your accommodation at midday. So it’s Adios, or, as we prefer to say hasta luego, see you later! Afternoon transfer (30–40 minutes approx.) to Havana airport.