Cuba / Itineraries

Historic Cuba


For clients with an interest in Cuban history, both old and new, this 14-night itinerary takes in many of the country’s most important destinations, starting in Havana and ending in Santiago before flying back to the capital.

  • Day 1 — Havana

    Clients will be met at Havana airport by a local representative followed by a short, 30 minute drive into Havana.

    Having checked in at the accommodation of their choosing, the remainder of Day 1 is free for you to go for a stroll, have something to eat and drink or simply relax at your hotel or casa particular.

    Suggested Accommodation: Havana Casa Particulars
    • — Havana, Malecon sunset
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    • — Mojito
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  • Day 2 — Havana

    One of the world’s most fascinating, exhilarating and iconic cities, Havana is an absolute must-visit on any holiday to Cuba.

    The original settlement, known as Old Havana or Habana Vieja, is located along the west bank of the city’s harbour-mouth. Although the city has sprawled out in numerous directions, the vast majority of Havana’s historic sites, places of interest and best accommodation can be found in this compact, walkable part of the city.

    Declared a UNESCO World Heritage site back in 1982, the intervening years have seen many of Old Havana’s numerous colonial buildings and public spaces restored to their former glory while, in stark contrast, others seem on the brink of collapse. It is this juxtaposition, played out across the city, that is one of the most compelling aspects of any visit to Havana.

    Your holiday begins with a guided walking tour of Old Havana, a great introduction to the historic heart of the city as you take in the history, colonial architecture and vibrant daily, goings-on of this UNESCO World Heritage city. Including the four main squares of Plaza de Armas, Plaza San Francisco, Plaza Vieja and Plaza de la Catedral, your guide will be on hand to guide you through all the main areas of interest and to answer any queries you may have.

    After sampling a Cuban cocktail you will then be picked and driven in a vintage car through ‘New’ Havana. Along the way you’ll drive past the Capitol Building, Revolution Square, the University of Havana, Hotel Nacional and former Presidential Palace before ending your first day in time for a late lunch.

    The rest of the day is at leisure for you to relax, perhaps take in a museum or simply wander the streets of Old Havana.

    Suggested Accommodation: Havana Casa Particulars Meals Included: Breakfast
    • — Havana, Plaza San Francisco
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    • — Havana, Parque Central
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  • Day 3 — Havana

    After breakfast, your guide will collect you from your accommodation and transfer you the short distance to the Morro Lighthouse & Castle, which guards the entrance to Havana’s harbour.

    After a brief explore, it’s just a short walk Fortaleza de San Carlos De La Cabana, one of the largest forts anywhere in the Americas.

    Referred to as either the largest, second largest or even third largest fort in the Americas, La Cabana Havana (as it is abbreviated to) is a vast 18th century fort that overlooks Havana from the eastern side of the bay.

    Construction began almost immediately, in 1763, and La Cabana Havana was completed in 1774. Such was the huge cost of building the fort that King Carlos III of Spain is said to have quipped that he was surprised he couldn’t see the fort from Spain. Expensive it may have been, but over the next couple of hundred years it did successfully guard Havana.

    From La Cabana, another short walk takes you to Cristo de la Habana, a 60-foot statue with panoramic views across the bay to Old Havana and beyond. From there you will follow the road down to the charming neighbourhood of Casablanca, home to the famous Hershey Train station. From Casablanca you can then catch one of the city’s iconic ferries back across the harbour to Old Havana.

    The rest of the afternoon is at leisure.

    Suggested Accommodation: Havana Casa Particulars Meals Included: Breakfast
    • — Havana, Morro Castle
  • Day 4 — Havana to Cienfuegos

    This morning you pack your bags for the 3-4 hour road transfer to Cuba’s south coast, beginning with the city of Cienfuegos.

    Often referred to as the Pearl of the South, the city of Cienfuegos is an attractive, maritime city located on Cuba’s south coast.

    At the heart of Cienfuegos, and just a short walk from the beautiful waterfront, is the city’s vast main square, Plaza Jose Marti, lined all four sides by grand civic buildings dating back to the colonial era, the most famous of which is undoubtedly the iconic Teatro Tomas Terry.

    A short taxi ride from the city centre is Punta Gorda, a narrow peninsula that juts out into the Bay of Cienfuegos and which was once the city’s most upmarket neighbourhood. Even today, this part of the city is still home to numerous beautiful buildings, including the famous Palacio del Valle & Club Cienfuegos, as well as much of the city’s limited accommodation.

    After checking in at your accommodation and having a bite to eat, the rest of the afternoon is at leisure. Why not pre-book a sunset boat trip around Cienfuegos Bay?

    Suggested Accommodation: Melia Union Meals Included: Breakfast
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    • — Cienfuegos, Governor's Palace
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  • Day 5 — Cienfuegos to Trinidad

    After breakfast, you will be met by your guide for a morning tour of Cienfuegos.

    After completing your tour and taking lunch locally, it is then a pleasant hour-long drive along Cuba’s Caribbean coast to the town of Trinidad.

    Small it may be, but the town of Trinidad on Cuba’s south coast punches well above its weight when it comes to visitor appeal and, after Havana, is the island’s number two cultural destination.

    Founded in 1514, Trinidad grew rich on the back of the sugar trade. The wealth this generated led to the building of numerous beautiful civic buildings and private homes, many of which are largely unchanged to this day. With so much of its original architecture still in place, and the colonial layout of the town centre largely untainted by modern development, Trinidad was declared a UNESCO World Heritage Site in 1988.

    Today, the historic centre of Trinidad is closed to traffic and wandering the town’s cobbled lanes it is hard not to be struck by the beauty of the town which is often described as an outdoor museum. For those who like traditional museums, the charming Museo Histórico Municipal, also known as Casa Cantero, is our top pick although the Museo Nacional de la Lucha Contra Bandidos will appeal to those with an interest in the Cuban Revolution.

    After checking-in at your accommodation, the rest of the day is at leisure.

    Suggested Accommodation: Trinidad Casa Particulars Meals Included: Breakfast, Lunch
    • — Cienguegos, Teatro Tomas Terry
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    • — Cienfuegos, Club
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    • — Cienfuegos, Palacio De Valle
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  • Day 6 — Trinidad

    After breakfast, your guide will meet you at your chosen accommodation for a morning tour of Trinidad.

    Pretty much every building in Trinidad’s historic centre has a story and this walking tour will provide a great introduction to the town and its history. Also included within the tour are visits to local cultural projects, one museum, a mock-up of the town and a drink at a local bar.

    The rest of the day is free for you to further explore Trinidad at your leisure.

    Suggested Accommodation: Trinidad Casa Particulars Meals Included: Breakfast
    • — Trinidad, Plaza Mayor
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    • — Trinidad, Museo Romantico
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    • — Trinidad, street
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  • Day 7 — Trinidad (Day trip Valley of Sugar Mills & Sancti Spiritus)

    Today, you will visit the Valley of the Sugar Mills and Sancti Spiritus on a full day tour before returning to Trinidad.

    Located between Trinidad & Sancti Spiritus, the Valley of the Sugar Mills was once the epicentre of the Cuban sugar industry and is still home to a number of atmospheric, decaying relics from that era. The most visited of these landmarks are Casa Gauchinango and Manaca-Iznaga whose haunting slave tower offers panoramic views of the valley.

    One of Cuba’s original ‘villages’, Sancti Spiritus, is one of the most attractive towns in Cuba and, precisely because most visitors choose to stay in Trinidad, one which has remained much more laid back.

    Sancti Spiritus remains, at heart, a small, country town, focused around the main squares of Parque Serafín Sánchez and Honorato del Castillo. Also included on your tour of town are the Casa de la Guayabera, the Parroquial Mayor church, Casa de la Trova, Ruben Martez Villena library and, most famous of all, the iconic Yayabo bridge. Lunch is included at a local restaurant before returning to Trinidad in the late afternoon.

    Suggested Accommodation: Trinidad Casa Particulars Meals Included: Breakfast
    • — Trinidad, Valley of the Sugar Mills
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    • — Sancti Spiritus, Parque Serafin
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    • — Sancti Spiritus, Puente Yayabo
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  • Day 8 — Trinidad to Santa Clara

    This morning you head north, on one of the most dramatic and scenic drives in Cuba, climbing high into the Escambray Mountains before continuing to the city of Santa Clara.

    Primarily famous for being the final resting place of Ernesto Che Guevara, Santa Clara is inextricably linked with the Cuban Revolution.

    It was in Santa Clara that the last battle of the Cuban Revolution was fought in 1958, led in part by Guevara, and culminating in the derailing of a government troop train. Within hours, General Batista had fled the island for good and a new phase in Cuba’s history had begun. Today, the very same train is preserved in a park setting within the city and serves as both a national monument and museum.

    However, Santa Clara’s main draw is undoubtedly Che Guevara’s Mausoleum and Monument which is located just outside the city centre. The Monument was opened in 1988 while the Mausoleum was added in 1997 after his remains were discovered in Bolivia and returned to Cuba.

    Having checked in at your accommodation there will be a tour of the main sites in Santa Clara including the Tren Blindado, Che Guevara’s mausoleum, Parque Vidal, La Caridad theatre and the Museum of the Fine Arts.

    Suggested Accommodation: Hotel Central Santa Clara Meals Included: Breakfast
    • — Santa Clara, Che Guevara
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    • — Santa Clara, Tren Blindado
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    • — Santa Clara, Parque Vidal
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  • Day 9 — Santa Clara to Camaguey

    Departing Santa Clara after breakfast, you should arrive at your next destination, Camaguey, in time for lunch.

    One of the original Spanish settlements in Cuba, Camaguey settled in its current location in 1528. In stark contrast to the vast majority of Spanish colonial cities, which tend to follow the same, very ordered structure, Camaguey is laid out in a seemingly chaotic mish mash of irregular streets heading in all directions and connecting with a multitude of squares of differing sizes. Getting lost is almost a given.

    Although over-shadowed by the likes of Havana & Trinidad, the historic centre of Camaguey is also home to some outstanding and varied architecture, reflecting the different styles of its long history and ranging from neoclassical to art nouveau. In recognition of its unique heritage, Camaguey was declared a UNESCO World Heritage Site in 2008.

    This afternoon there will be a tour of the city with transport in one of its iconic rickshaws.

    Suggested Accommodation: Melia Gran Camaguey Meals Included: Breakfast
    • — Camaguey, Plaza San Juan
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    • — Nuestra Senora De La Merced
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    • — Camaguey, Rickshaws
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  • Day 10 — Camaguey to Bayamo

    The morning is at leisure in Camaguey for you to either explore on your own or perhaps book one of our optional Trips, such as to the famous Camaguey Ballet.

    After lunch, you will be collected from your accommodation for the onward transfer to Bayamo.

    Older than either Havana or Santiago, the charming, colonial town of Bayamo is an easy-going kind of place and one that most Cubans hold dear.

    During the wars of independence from Spain, Bayamo was an insurgent stronghold and, in an act of defiance, large parts of the town were burned to the ground by its own residents during the fighting. Carlos Manuel de Cespedes, viewed by many as the father of the independence movement, was also a native of Bayamo and famous for setting the slaves on his nearby plantation free.

    Despite this tumultuous period in its history, Bayamo is still an attractive town with plenty of graceful colonial-era architecture to admire including San Salvador cathedral, the Bayamo theatre, and Parque Cespedes.

    Another, less well-known feature of the town, and a welcome one at that, is the relative lack of motor traffic – the majority of Bayamo residents still get about by bike or horse.

    Suggested Accommodation: Hotel Royalton Meals Included: Breakfast
    • — Camaguey Ballet
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    • — Bayamo, Main street
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    • — Bayamo, Parque
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  • Day 11 — Bayamo to Santiago

    This morning there will be a tour of Bayamo’s followed by lunch and then an onward transfer to Santiago de Cuba.

    (If you wish, you can extend your stay in Bayamo by a day and hike to La Plata, Fidel Castro’s remote revolutionary hideaway in the Sierra Maestra).

    Santiago might be the island’s second largest city, but it’s probably best that you don’t mention that while you’re there. While only a fraction of the size of Havana, the citizens of Santiago are fiercely proud of their city and, in many ways – be it ethnicity, traditions or temperament – very different.

    More ethnically mixed than other parts of the island, Santiago could be considered as the New Orleans of Cuba, notable as much for its rich cultural heritage of music and dance as it is for its equally varied architectural styles.

    For those with an interest in modern Cuban history, Santiago is regarded as the birthplace of the Cuban Revolution and visits to both the Moncada Barracks (where the Revolution began) and City Hall (where Fidel Castro declared final victory) are a must for enthusiasts.

    On arrival, check in at your accommodation. The remainder of the day is at leisure.

    Suggested Accommodation: Hotel Casa Granda Meals Included: Breakfast
    • — Bayamo, Town centre
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    • — Bayamo, Church exterior
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    • — Santiago, Parque Cespedes
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  • Day 12 — Santiago

    Starting after breakfast, there will be a full day tour of the city and its surroundings starting with many of the city’s highlights including Revolution Square, the Moncada Barracks, Museum Diego Velazquez and the Santa Ifigenia cemetery to witness the changing of the guard.

    The tour then continues to the outskirts of the city and the UNESCO World Heritage listed San Pedro de la Roca fortress before a short boat journey takes you to Cayo Granma for lunch. The day ends with a stroll around the city’s central Parque Cespedes before you return to your accommodation.

    The rest of the day is at leisure although a visit to the city’s Casa de la Trova this evening is highly recommended. Before you go, and if you’ve got the energy, why not book a private, hour-long salsa lesson to hone your moves?

    Suggested Accommodation: Hotel Casa Granda Meals Included: Breakfast
    • — Santiago, Moncada
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    • — Santiago, Santa Ifigenia cemetery
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    • — Santiago, Fort
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  • Day 13 — Santiago

    Today, you have the option of relaxing at your accommodation, exploring further on your own or booking one of optional Trips to sites outside the city such as El Cobre or La Gran Piedra.

    Suggested Accommodation: Hotel Casa Granda Meals Included: Breakfast
    • — Santiago, Spanish Steps
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    • — El Cobre
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    • — La Gran Piedra
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  • Day 14 — Santiago to Havana

    Depending on flight times, you will be collected from your accommodation and transferred the short distance to Santiago airport in time for your flight back to Havana.

    On arrival in Havana you will be met at the airport and transferred to your chosen accommodation in the city.

    The rest of the day is at leisure.

    Suggested Accommodation: Havana Casa Particulars Meals Included: Breakfast
    • — Santiago, dominos
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    • — Havana, Capitol building
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    • — Havana, street dancing
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  • Day 15 — Havana to Home

    Your final day in Havana is at leisure for you to relax, explore further or perhaps do a bit of last- minute shopping.

    Depending on your flight time, you will be collected from your accommodation for the private transfer back to Havana airport and your onward journey home.

    Meals Included: Breakfast
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    • — Havana, musicians
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Please Note

This itinerary is no more than a sample idea which can be tailor made to your exact requirements.

The 'From price' is for travel in September and is based on two adults sharing the same room throughout. Supplements apply for sole occupancy.

The quoted price does not include international flights.

Beach Extensions

Beach Extensions

For clients wishing to extend their holiday with time at one of Cuba’s numerous beach resorts there are numerous options although, for logistical reasons, we would suggest sticking to the western half of the island. Please call or email for advice.

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