Cuba / Itineraries

Historic Cuba

  • Aerial view over Trinidad, Cuba at sunset

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

    The vast majority of our clients travel to Cuba from the UK and mainland Europe, with flights from the region touching down from late afternoon onwards.

    On arrival, clients will be transferred the short distance from Jose Marti airport to their choice of accommodation in the city, after which what remains of the day is at leisure.

    Suggested Accommodation: Havana Casa Particulars
    • Sunset over the Malecon in Havana, Cuba
      — Havana, Malecon sunset
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    • Mojitos at a bar in Havana
      — Mojito
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    • Paladar restaurant in Cuba
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  • Day 2 — Havana

    In a country full of historic towns and cities, none are on anything quite like the same scale as the nation’s capital, Havana.

    Although not Cuba’s oldest settlement, nor even its original capital, Havana is the island’s largest city by some way and one that is awash with historical sites dating all the way from the early years of the Spanish colonial empire right up to the Cuban Revolution of the 1950s.

    The city’s original settlement, known as Old Havana (or Habana Vieja in Spanish) is located at the western end of the city and is so jam-packed with historic buildings and spaces that, in 1982, it was declared Cuba’s first UNESCO World Heritage site.

    Not only is Old Havana where most of the city’s main sites of interest are located, it is also home to much of the city’s best accommodation and it is therefore here that the vast majority of our clients opt to stay.

    Accordingly, after a relaxing breakfast at your hotel or casa particular, you will meet up with your guide for a morning’s walking tour of Old Havana. Strolling between the four main plazas, your guide will run through the city’s colourful history, point out the most important buildings and answer any queries you may have.

    At the end of this walking tour, and a quick drinks break, you will have the opportunity to see something of New Havana, this time from the back of a classic American car.

    Along the way, you’ll drive through Revolution Square, past the University of Havana & Necropolis Cristobal Colon, around the Embassies and mansions of Miramar and back along the iconic seafront promenade known as the Malecon.

    At the end of this diverse, double-header, the remainder of the day is free for you to explore on your own, perhaps taking in a museum such as the grand Museum of the Revolution or simply to relax.

    Suggested Accommodation: Havana Casa Particulars Meals Included: Breakfast
    • Plaza San Francisco in Old Havana
      — Havana, Plaza San Francisco
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    • Havana Cuba Parque Central
      — Havana, Parque Central
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    • Classic car tour of Old Havana
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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 from there to Fortaleza de San Carlos De La Cabana, the third largest fort in the Americas. La Cabana, as it is known, was built during the second half of the 18th century and in response to the seizing of Havana by British forces.

    Significantly larger than the Morro Castle, La Cabana certainly served its purpose as the city was never successfully attacked again. Ironically, La Cabana didn’t finally ‘fall’ until 1959 when, in the final days of the Cuban Revolution, the local garrison surrendered without a fight.

    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
    • Morro Castle in Havana, Cuba
      — Havana, Morro Castle
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    • La Cabana castle Havana
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    • Casablanca Havana
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  • Day 4 — Havana to Cienfuegos

    Departing after breakfast, it is a 3-4 hour road transfer from Havana on the island’s north coast to the city of Cienfuegos on its south coast.

    With a picturesque location besides the Bay of Cienfuegos, the area was first settled by indigenous Tainos although the modern city of Cienfuegos was established by French settlers who moved here in the early 19th century.

    In that respect, Cienfuegos stands apart from the original ‘villages’ founded by the early Spanish colonists in Cuba. Being relatively new, and with French rather than Spanish influences, Cienfuegos also looks and feels very different from any other town or city in Cuba.

    This is most apparent in the Punta Gorda district of the city, once the smartest neighbourhood in Cienfuegos with plenty of remaining mansions that would not look out of place in New Orleans.

    A short drive away, the compact city centre is largely focussed on Plaza Jose Marti, surrounding which are a number of grandiose civic buildings as well as the charming Teatro Tomas Terry.

    Having checked in at the accommodation of your choice, the rest of the day is free for you to relax or explore on your own.

    Suggested Accommodation: Melia Union Meals Included: Breakfast
    • Walking tour of Cienfuegos
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    • The Governor's Palace in Cienfuegos
      — Cienfuegos, Governor's Palace
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    • Boat tour of Cienfuegos Bay in Cuba
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  • Day 5 — Cienfuegos to Trinidad

    This morning, you will meet up with your local guide for a morning tour of Cienfuegos (alternatively, you can do the tour the day before, shortly after arrival from Havana).

    On completion of your city tour, and having had a bite to eat, you will depart Cienfuegos for the short, hour-long drive along the coast to Trinidad.

    Founded in 1514 by Diego Velazquez, Trinidad is amongst the smallest of Cuba’s original, colonial settlements but is second only to Havana in terms of visitor numbers; it doesn’t take long to work out why.

    The historic heart of Trinidad is an unblemished, picture postcard of the island’s colonial past with cobbled streets, picturesque plazas and elegant architecture wherever you look.

    Often described as a living museum, it will come as no surprise to learn that Trinidad was declared a UNESCO World Heritage site in 1988.

    After checking-in at your chosen hotel or casa particular, the rest of the day is at leisure.

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

    After a leisurely breakfast, you will meet up with your guide for a morning’s walking tour of Trinidad’s pedestrianized town centre.

    Almost every structure in Trinidad’s historic centre has a story to tell and your local guide will be on-hand to point out the town’s most important historic sites as well as answer any questions you may have.

    Included in the tour is a visit to a museum but there are several in town worth visiting so, at the end of the tour, and after a break for lunch, we suggest you head back out and explore on your own.

    Museums that we would particularly recommend include the Museo Romantico, Casa Cantero and the snappily titled Museum of the Struggle Against Bandits.

    In addition to being an historic and beautiful town, Trinidad also plays host to numerous bars (be sure to visit La Canchanchara for their signature cocktail) restaurants and live music venues, all within easy walking distance.

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

    The region around Trinidad was once the heart of Cuba’s sugar growing industry and today you will head out on a full day Trip (excursion) to visit the famous Valley of the Sugar Mills and nearby town of Sancti Spiritus.

    Like Trinidad, Sancti Spiritus is one of Cuba’s original settlements or ‘villages’ and features a charming main square, Parque Serafín Sanchez, numerous colonial-era buildings and the most historic bridge in Cuba, Puente Yayabo.

    If it were located almost anywhere else in Cuba Sancti Spiritus would be a huge tourist draw. The proximity of Trinidad means that it receives relatively few visitors which, conversely, simply adds to its appeal.

    Lunch is included at a local restaurant as part of the tour before you return to Trinidad in the late afternoon.

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

    This morning you will pack your bags and head north from Trinidad, up and over the spectacular Escambray Mountains before arriving in the city of Santa Clara.

    Although Santa Clara can trace its history back to the late 17th century, unlike the towns and cities you have visited thus far, it is primarily famous for its role in modern Cuban history, specifically the Cuban Revolution.

    It was here that the last fighting of the war took place with a twin pronged attack on the city by forces led by Camillo Cienfuegos and Ernesto Che Guevara.

    The detachment under the command of Che Guevara successfully derailed a government troop train sent to re-enforce Santa Clara before enforcing the city’s total surrender on 31st December. Within hours, the Revolution was over.

    Today, the troop train in question forms part of a national monument and museum known as the Tren Blindado, located within the city centre in an attractive park setting.

    As a result of the pivotal role he played in the Battle of Santa Clara, on the outskirts of the city are its dual main draws, the monument to Che Guevara that was erected in 1988 as well as the Mausoleum which was subsequently added in 1997 after his remains were returned to Cuba from Bolivia.

    On arrival in Santa Clara, there will be an afternoon’s tour of the city’s main sites including the aforementioned reminders of the Cuban Revolution as well as its colonial history in the form of Parque Vidal, the Museum of Fine Arts and La Caridad theatre.


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

    Santa Clara is located pretty much in the centre of Cuba and from here you will begin your journey into the eastern half of the island, starting with the city of Camaguey.

    The third largest city on the island, Camaguey moved from its original coastal location to its current site in 1528, making it one of the oldest cities in Cuba.

    Alas, moving inland didn’t protect the city from marauding pirates and, in the following century, it was looted and largely burned to the ground by that most famous of pirates, Henry Morgan.

    In order to prevent any such repeat, the city authorities re-built the city with a maze-like layout designed to confuse any wannabe attackers and future tourists.

    More than just a confusing mish-mash of streets crossing each other at irregular angles, the centre of Camaguey features a variety of eclectic architectural styles and numerous handsome buildings. This, together with its colourful history, led to the city being declared a UNESCO World Heritage site in 2008.

    Having arrived in time for lunch, the afternoon will be spent exploring the city from the comfort of one its iconic cycle rickshaws.

    Suggested Accommodation: Melia Gran Camaguey Meals Included: Breakfast
    • Plaza San Juan de Dios in Camaguey, Cuba
      — Camaguey, Plaza San Juan
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    • The church of Nuestra Senora de la Merced in Camaguey, Cuba
      — Nuestra Senora De La Merced
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    • Rickshaws are popular with visitors to Camaguey in Cuba
      — Camaguey, Rickshaws
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  • Day 10 — Camaguey to Bayamo

    The first part of the day is free for you to relax at your hotel, explore Camaguey on your own or perhaps book one of our optional city Trips, perhaps to its world-famous ballet company to catch a glimpse behind the scenes.

    After lunch, you will be collected from your accommodation and continue your journey east with an approximate three hour drive to Bayamo.

    Whereas Santa Clara is now primarily famous for the starring role it played in the final outcome of the Cuban Revolution, the small town of Bayamo is synonomous with a far earlier conflict, namely Cuba’s long struggle for independence from Spain.

    During this drawn-out conflict, Bayamo was a leading bastion of the independence movement, so much so that a large part of the town was burned to the ground by its own citizens rather than let it fall into enemy hands.

    Bayamo was also home to Carlos Manuel de Cespedes, one of the most important figures in Cuban history and remembered by many for freeing the slaves on his family plantation.

    An attractive, laid-back town, Bayamo has a number of colonial-era buildings worth visiting including San Salvador Cathedral and the town’s theatre.

    Having checked in at your accommodation, why not head out and explore Bayamo utilising one of the numerous horse-drawn carriages for which the town is famous?

    Suggested Accommodation: Hotel Royalton Meals Included: Breakfast
    • The world renowned Camaguey ballet in Cuba
      — Camaguey Ballet
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    • The main street in Bayamo Cuba
      — Bayamo, Main street
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    • Locals in Bayamo's central Parque
      — Bayamo, Parque
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  • Day 11 — Bayamo to Santiago

    After a leisurely breakfast, the morning will be spent on a guided tour of Bayamo. Departing from town after lunch, it is then an approximate two-hour drive to the city of Santiago de Cuba.

    (If you wish to extend your stay in Bayamo, a popular day Trip we can arrange is the hike to Fidel Castro’s revolutionary hideaway of La Plata, hidden deep within the nearby Sierra Maestra).

    Founded in 1515 and the capital of Cuba for most of the 16th century, Santiago de Cuba is the island’s second largest city. Home to Cuba’s most impressive castle and oldest cathedral, Santiago de Cuba is also both the birthplace of the Cuban Revolution as well as the final resting place of its iconic leader, Fidel Castro.

    In addition to its many historic sites of interest, Santiago de Cuba is also the island’s most ethnically diverse city and a vibrant cultural melting pot when it comes to literature, music and dance.

    Birthplace of salsa, home to many of Cuba’s most famous musicians and the original site of the world-famous Bacardi rum factory, this is city that very much knows how to have a good time.

    On arrival in the city, the remainder of the day is free for you to relax at the hotel or go for a quick explore.

    Suggested Accommodation: Hotel Casa Granda Meals Included: Breakfast
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    • Exterior of church in Bayamo Cuba
      — Bayamo, Church exterior
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    • Parque Cespedes in Santiago de Cuba
      — 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 (aka the Morro Castle) 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
    • 3 hour tour of Santiago de Cuba
      — Santiago, Moncada
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    • Santa Ifigenia cemetery in Santiago de Cuba
      — Santiago, Santa Ifigenia cemetery
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    • 6 hour tour of Santiago de Cuba
      — Santiago, Fort
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  • Day 13 — Santiago

    Today, you have the option of relaxing at your chosen hotel, further exploring Santiago on your own or perhaps booking one of our optional Trips outside of the city.

    The two most popular excursions from Santiago are to El Cobre, Cuba’s most important religious site, and La Gran Piedra, a giant boulder and National Park located in the cool hills, north-east of the city.

    Suggested Accommodation: Hotel Casa Granda Meals Included: Breakfast
    • Spanish steps in Santiago de Cuba
      — Santiago, Spanish Steps
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    • Day trip to El Cobre from Santiago de Cuba
      — El Cobre
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    • La Gran Piedra near Santiago de Cuba
      — La Gran Piedra
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  • Day 14 — Santiago to Havana

    Flight schedules between Santiago and Havana are variable, so plans for today are very much flight dependent.

    At the allotted time, you will be collected from your hotel and transferred to the nearby airport for the approximate ninety-minute flight back to Havana.

    On arrival in Havana, you will be transferred to your chosen accommodation in the city, hopefully in time for a grand, final night out such as the Legendarios del Guajirito.

    Suggested Accommodation: Havana Casa Particulars Meals Included: Breakfast
    • Boys playing dominos in Santiago de Cuba
      — Santiago, dominos
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    • Old taxi driving past the Capitol building in Old Havana
      — Havana, Capitol building
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    • Havana Cuba Street Dancing
      — Havana, street dancing
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  • Day 15 — Havana to Home

    The vast majority of flights to the UK and Europe depart Havana from the late afternoon onwards so, as a bare minimum, you should have a full morning in which in which to go for a stroll, take in a final museum of perhaps indulge in some last-minute shopping.

    You will then be collected from your accommodation for the private transfer back to Havana airport and your overnight journey back home.

    Meals Included: Breakfast
    • Shopping in Havana
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    • Musicians in Old Havana
      — Havana, musicians
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    • Airplane departing into the sunset
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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.

Cuba holiday beach extension at Memories Jibacoa

Suggested Accommodation

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