Fly to Havana where you’ll be met and taken to your accommodation in the heart of the city – a beautifully restored 20th century house on the traditional Malecón. You’ll find yourself in between modern Havana and the city’s historic centre, where cobbled streets lead to wedding cake-style churches, tiny shops and colonial mansions decorated in faded pastel colours. Balconies with ornate railings and shuttered windows add to the air of time-eroded gentility.
You’ll visit Old Havana’s four historic plazas – Plaza Vieja, Plaza de la Cathedral, Plaza San Francisco de Asis and Plaza de Armas – as well as the haunts of 1930s gangsters, the notorious Al Capone amongst them. As you cruise around in an open-top American car, you’ll have the opportunity to take in some beautiful views of the city.
Stay: Three nights in a suite at Malecon 663 – bed & breakfast
On your way to Trinidad you’ll call in at the Che Guevara Memorial and museum on the site of one of his most celebrated battles at Santa Clara, regarded as the turning point in the revolutionary war. Travelling on to Trinidad – a picturesque town famed for its multi-coloured houses – you will be presented with another side to Cuba. You’ll be staying beside scenic Santa Rosa Valley, in a hotel that was originally one of the oldest houses in Trinidad.
A walking tour with an expert guide will introduce you to the history and sites that have helped make Trinidad a UNESCO World Heritage Site. You’ll also visit a local sugar plantation to gain an insight into the hardships of slavery and its relation to the sugar industry.
Stay: Two nights in a double room at Finca Kenia.
Don’t worry if you lose yourself in Camaguey city – its labyrinthine streets, blind alleys and passages were deliberately created to confuse and confound the invading pirates who continually attempted to sack the town in the 16th century. And anyway, your guide will be able to navigate the cobblestone plazas, romantic squares, beautiful parks and over-sized churches in the baroque style.
Stay: One night in a double room at Casa Miriam Guerra – bed & breakfast
Today you will be transferred to your inviting cabana at the foot of the Sierra Maestra Mountains. Students of the 1959 revolution will find themselves in their element here. As well as being Cuba’s highest mountain, the Sierra Maestra was the natural hideout for Fidel Castro, Che Guevara and the band of revolutionaries that eventually overthrew the existing government and ended America’s domination of the country.
Your accommodation is located in the village of Santo Domingo where you can hike to Castro’s old HQ, medical centre, radio station, museum and home. You’ll also be able to go horse riding, mule trekking and walking through the gorgeous local countryside. Those feeling more active can opt to hike the Pico Real del Turquino – the highest point in the country.
Stay: Two nights in a double room at Villa Santo Domingo – bed & breakfast
Santiago de Cuba
You’ll find Cuba’s second largest city a place of celebration, music and monumental architecture. Originally founded in 1515, Santiago de Cuba is beautifully situated between towering mountains and the Caribbean Sea. During your stay you’ll be able to visit coffee plantations, plus the beaches, lakes and mountains of Baconao Park.
A half day tour will introduce you to the city’s historic centre, the revolutionary 26th July Museum, the Sanctuary of El Cobre, the Moncada Barracks and the delightful Cespedes Park. Later you will visit the San Pedro de la Roca Castle, a brilliant example of Spanish-American military architecture, where you can watch the sunset over the Bay of Santiago.
Stay: Two nights in a double room at the Imperial – bed & breakfast
Your Classic Cuba tour now takes you to the island’s main cacao producing town, located in Guantanamo. Baracoa was originally a Spanish settlement so remote that it could only be reached by sea. Today you can drive there but it remains unspoiled with a timeless atmosphere. Here you’ll find the only remaining cross brought to the New World by Christopher Columbus.
A walking tour will show you the local church, the original fortress built to repel pirates and La Punta Fortress. Then the UNESCO-sponsored Alexander Von Humboldt National Park – where wide rivers, humid jungle and mountainous terrain encourage an incredible natural biodiversity – invites you to explore. Expect to discover parrots, lizards, hummingbirds, Cuban solenodon and a variety of exotic and endemic plants.
Stay: Three nights at the Villa Maguana – bed & breakfast
A short domestic flight from Baracoa will take you back to the salsa bars and lively nightlife of Havana.
The next morning you’ll be able to attend a rehearsal of the world renowned National Ballet Company before transferring to the airport for your evening flight out of Havana.
Stay: One night in a suite at Malecon 663 – bed & breakfast
Rob was fab - super knowledgeable and really helpful. Will definitely use his services again.- J and CR, Malaysia, 2016