Cuba Heritage Holidays

Step back in time in Cuba and discover cities built by conquistadores and laced with legends of pirates, historic sugar mills and colonial plantation.

Cuba is chock-full of world-class colonial cities and citadels. Peel back the layers of the country's rich history on a journey visiting handsome cities founded by conquistadores, fortresses laid siege by pirates, settlements little-changed since the 16th-century, illustrious mansions-turned-museums and historic plantations.

From £9999 per person

Cuba is home to one of the world’s greatest collections of colonial architecture, including illustrious palaces, mansions, country houses and castles spanning more than 400 years of history. As a chief port of call for ships on the way to the New World, its colonial era began with Columbus’ first landing in 1492 and his subsequent claiming of the island for the Spanish crown. Cuba became the jewel of the Spanish Empire, and the new settlers transformed the landscape, building ports, castles, towns and plantations that can still be seen to this day. Some places, like UNESCO-listed Trinidad, have been virtually frozen in time, with exquisite architecture and hardly any modern structures at all, while cities such as Havana and Santiago de Cuba have retained their historic centres. In fact, Cuba has nine World Heritage Sites, seven of which are inscribed to the list for their historic and cultural significance.

Visitors on the colonial trail in Cuba are spoilt for choice when it comes to exciting destinations. Alongside Trinidad and Old Havana, the charming city of Baracoa on the island’s far-eastern tip was Cuba’s first settlement and a must-see for anyone exploring the island’s history. For something a bit different, the pretty city of Cienfuegos is celebrated for its eclectic influences and architecture that includes a Spanish fortress, a French-styled Arch de Triumph, and a lavish palace inspired by Moorish architecture. Alternatively, little-known Remedios is a great place to experience colonial Cuba without the crowds. There are also a vast array of museums showcasing the island’s Spanish colonial grandeur and history, including former homes of nobility crammed full of antiques and important artefacts. Tourists can visit historic sugar mills and rural settlements to learn more about the island’s important agricultural legacy and the brutal history of slavery.

The bays of this beautiful island once attracted smugglers and pirates too. The trappings of empire made it even more appealing to potential raiders and corsairs who haunted Cuba’s waters for centuries. Cuba’s coastal castles and fortifications are testament to this history, where today these colourful legends and swashbuckling stories are really brought to life. But Cuba’s history extends even further back to a time when the island was populated by indigenous Indians – a layer of the island’s heritage that has recently been rediscovered.

Western Cuba – The treasures of Havana

On an island brimming with glittering colonial treasures, it can be difficult to know where to explore first. The country’s capital Havana, dubbed the Pearl of the Antilles during the colonial era, is the most obvious place to start. Founded in 1519, by the 17th century Havana had matured into one of the Caribbean’s main shipbuilding hubs and was the main stop-off for ships laden with treasures from the New World. The famous Morro Castle was built on a rocky outcrop at the entrance to the bay to protect the port from marauders and to act as a beacon for friendly ships. The tradition of firing the fortress canons at 9pm to announce the closing of the city walls continues to this day and visitors to the castle grounds can still witness marching guards dressed in Spanish colonial military uniforms setting off the canons. As such, Old Havana and its Spanish colonial fortifications are UNESCO-listed for their historical significance and colonial splendour.

Soaking up the atmosphere by strolling through the grand streets and squares of the old city, overlooked by countless architectural masterpieces, is one of the simple pleasures of Havana. The state of decay of some buildings only adds to the faded charm of the capital’s old quarter and there are many museums housed in converted colonial mansions, including the fascinating Museo del Ron, which takes visitors on a journey through the history of traditional rum production in Cuba.

Of the many historic squares in Old Havana, Plaza de Armas, flanked by 16th-century Castillo de la Real Fuerza and the Palacio de los Capitanes Generales (Palace of the General Captains) is a must-see for history enthusiasts. The 18th-century palace is the former seat of the governors of Havana and you can see its intact colonial interiors by touring the Museo de la Ciudad (Museum of the City of Havana) now contained in the building. To learn more about the country’s Afro-Cuban heritage linked to the trafficking of slaves from Africa during the colonial period, you should not miss a visit to Casa de Africa (House of Africa), housed in a former colonial palace. It showcases the culture and history of Africa with collections from 27 African countries, sacred objects used in Afro-Cuban religions, and a clutch of artefacts belonging to Fidel Castro.

Central Cuba – Three Jewels of the Spanish Empire

The jewel in Cuba’s colonial crown, Trinidad, in south-central Cuba, is the most important stop on the country’s Spanish heritage trail. The most exquisitely preserved of the country’s cities, its handsome streets harking back to the early days of colonial Cuba have earned it UNESCO World Heritage Site status. Founded by Diego Velazquez in 1514, it was one of the first seven villages settled by the Spanish. Its old world charm is heightened by the lack of modernity in a place where horse and carts are as common a sight as cars. The city has a more rustic feel than Old Havana and walking its cobbled streets, appreciating the colourful blue, green, red and yellow facades of its colonial mansions really feels like stepping back in time.

Characterised by arched colonnades, high ceilings, balconies and walled atriums, many of the city’s historic homes have been converted into restaurants still sporting gracefully aging interiors, and some have become museums. In fact, Trinidad has the most museums per capita in the country. At the heart of colonial Trinidad, the Plaza Major is overlooked by a trio of museums showcasing the town’s rich heritage and stuffed with valuable artefacts. The Museo Romántico (Romantic Museum) is full of antique furniture from the 1800s, while Museo de Arquitectura Colonial (Museum of Colonial Architecture) is a celebration of 18th and 19th century domestic architecture. Both are unmissable sights on any tour of colonial Cuba.

Trinidad is UNESCO-listed alongside the Valley of the Sugar Mills that once made the city wealthy. A living museum of Cuban sugar production during the 18th and 19th centuries, the valley features the ruins of more than 70 mills, including watchtowers and barracks that are a reminder of the many slaves brought from Africa to work the plantations. A similar snapshot of colonial agricultural life can be seen in the Viñales Valley too, where tobacco farming has remained unchanged for centuries. Between the rounded foothills of the Sierra del los Órganos, fragrant russet fields, criss-cross the landscape and ox-drawn ploughs and carts are still used instead of tractors.

In an island chock-full of other colonial cities and sights, Remedios, near the coast of north-central Cuba, is a little-known gem with a mysterious history that’s perfect if you want to escape the crowds. It was founded between 1513 and 1524 and may have been settled before Trinidad. Its origins are slightly obscure because it is rumoured that the conquistador, Captain Vasco, kept it hidden from the Spanish crown so that he could avoid tax payments. The well-kept 17th-century Spanish architecture of the city centre – arched colonnades painted in bright yellows and blues, attractive leafy squares and terracotta rooftops – led to the city being named a National Historic Monument in 1980. Travellers lucky enough to visit the city around Christmas can experience an early colonial ritual brought to life, when one of the Caribbean’s largest and oldest traditional festivities – the Parrandas – is held in the city. Of Remedios’ many treasures, the historic church looking onto the main square contains 13 gold altars that were once painted white to hide them during frequent raids by pirates and corsairs.

Another early colonial city with its origins in the 16th-century, Camagüey’s historic centre is also inscribed to the UNESCO World Heritage list. A medieval-style rabbit’s warren of serpentine streets and little squares, tales of pirates and marauders abound and a walking tour of its preserved streets brings many of the stories to life. The village became a target for pirate attacks in the 17th century. In fact, the centre had to be rebuilt after the corsair Morgan’s attack in 1668. With a pronounced colonial air, many of its residential buildings have a hybrid architectural style unique to the city, with heavy wooden eaves and lathed balustrades covering the windows.

Eastern Cuba – Legends of Pirates and Conquistadors

Like Camagüey and other early colonial cities, Santiago de Cuba, in the south-east of the island, also had to fend off pirates and marauders attracted by rich pickings. One method was to build fortifications to protect the city and Santiago de Cuba’s San Pedro de la Roca Castle is considered the best preserved and most complete example of Spanish-American military architecture. As pirates were most likely to attack from the sea, the 17th-century castle overlooks the coastline in a prime elevated position on the promontory. As a happy consequence, it offers visitors wonderful views over the bay.

Santiago de Cuba was a stronghold of the Spanish occupation and has a long history as one of the island’s earliest colonial settlements and the place where the first slaves arrived from West Africa to work in the coffee and sugar plantations that made the island rich.

In Santiago visitors can find the elegant house that once belonged to the first governor of Cuba, Diego Velazquez, which is the oldest residential building on the island, dating to 1515. Now it offers one of the best insights into colonial lifestyles in Cuba as the home of the Museo del Ambiente Cubano (Museum of the Cuban Historical Environment), full of priceless antiques and curiosities from the period. Built by conquistadores, the colonial quarter to the west of the city is laid out on a grid system emanating from Parque Céspedes´ square. More a square than a park, the first cathedral in Cuba was built here in 1522, though it was subsequently damaged by pirates and earthquakes.

Further east of Santiago, Baracoa is situated on the island’s farthest tip. Called the First City, it was officially founded in 1511, though Columbus reputedly landed here in 1492 and claimed it with a cross. Its position sandwiched between vertiginous peaks and emerald sea, once made it a natural haven for smugglers and pirates. But it was the beauty of its dramatic setting that first struck Columbus. The explorer wrote in his logbook that it was “the most beautiful place in the world ...I heard the birds sing that they will never ever leave this place”. Vestiges of the Spanish influence remain, such as the fortifications of El Castillo, Matachín and La Punta, giving Baracoa a pronounced colonial atmosphere.

What colonialism destroyed

Many of the names of the island's most well-known places including Havana, Camaguey and Baracoa come from the language of the Taíno Arawak Indians who preceded the colonialists on the island. Though the native population was virtually wiped out by the Spanish, Baracoa is one of the only locations where their descendants still live and practice their ancient traditions. The palm-thatched huts common in the region are similar to those built centuries ago by the indigenous group and some farmers till the soil using a long, sharpened pole which was known to the Taíno as a coa. In Baracoa there is even a monument to the Taíno chief Hatuey, a local hero who led an indigenous uprising against the Spanish but was betrayed and killed.

For travellers who want to delve deeper into the mists of time, there is a fantastic museum located around an archaeological site near Guardalavaca, in the eastern province of Holguin, that’s well worth a visit. The region has long been home to a native population and Chorro de Maita offers an opportunity to see the remains of an excavated pre-Columbine village and burial site. You can also experience Cuba’s forgotten history brought to life at the neighbouring Taíno Village, a real-size recreation of an indigenous community featuring native dance rituals and other high-energy shows.

Following The Slave Route

From the 16th century until the late 19th century, the colonialists brutally exploited more than a million people who were brought from Africa to Cuba as slaves. They were routinely punished with beatings, made to live in unsanitary barracks and forced work for more than 16 hours a day. Despite the British abolition of the Atlantic slave trade in 1807, Cuba’s slaves were not emancipated until 1886. As such, Santiago has the most pronounced Afro-Cuban culture in Cuba, where it’s estimated that around 60% of the Cuban population are descendants from slaves. But the African influence is everywhere in Cuba and therefore the country’s culture reflects the nation’s strong links to its African roots.

There are places in Cuba where you can follow the trail of Cuban slavery and one of the best to do so is the Museo Nacional de la Ruta del Esclavo (Slave Route Museum), created as part of a UNESCO project proposed by Haiti back in 1993. Named The Slave Project, UNESCO aimed to build a better understanding of the consequences of slavery in the world and gain more mutual understanding of the relationship between Africa and the Americas. In 2009 Cuba followed this initiative by opening the Slave Route Museum in Matanzas, 100 km from the capital city and just 50 km from Varadero. Located on the grounds of a castle known as Castillo de San Severino, this museum is the first of its kind in the Americas and is split into four rooms, showcasing the different aspects of slavery in Cuba and how the African heritage influenced and shaped up the island’s culture: The Commander’s House, Archaeological Exhibition, Slavery Exhibition and Orishas Exhibition. It’s a wonderful place to spend a morning or afternoon immersing in Cuba’s colonial past and culture.

If you want to dig deeper into Cuba’s slavery past there are a few other places you can visit to immerse deeper into the history. You can start off with the beautiful UNESCO-listed Archaeological Landscape of the First Coffee Plantations in the South-East of Cuba, which comprise the physical remains of 19th-century coffee plantations in the foothills of the Sierra Maestra mountain range. These remains are the last living evidence and unique testimony of agricultural exploitation in a difficult terrain. They tell the story of the slaves’ struggle to conquer wild, untameable nature and the brutal labour conditions they were subjected to when working these lands. Remarkable relics still standing include intricate production systems that showcase the skill and creativity of the enslaved engineers, carpenters and builders. Also on show you can find the remnants of impressive hydraulic engineering systems, sophisticated domestic architecture and elaborate roadways.

For an encounter with the more spiritual living heritage of Cuban slaves in the capital, you can find contemporary examples of their vibrant culture in the municipalities of Regla and Guanabacoa. With a large Afro-Cuban community, these districts in Havana are where the African slave roots survived the most untouched. Guanabacoa is famous for the large number of devotees of the African Yoruba religion that the slaves brought to Cuba. The district is famous for its babalawos (Yoruba priests) and the practice of Santería, a syncretic religion that unites West African Yoruba beliefs with the Catholic saints and values that the Spanish Empire brought to Cuba. Visit the National Sanctuary of Our Lady of Regla, built in the 17th century to honour a black virgin dressed in blue, befitting her title as Queen of the Seas. If you happen to visit it on 7th September, you will get to witness the pilgrimage of hundreds of devotees who flock here to make promises, do penance and bring offerings to the virgin.

The contrasts of colonial Cuba - a story of greatness and hardship

As is to be expected Cuba’s history of colonialism was full of high and lows. Beneath the surface of imposing architecture and exuberant wealth was the suppression of hardworking slaves and a long-lasting struggle to achieve independence against the colonists and overthrow the Spanish rule. Admiring the grandeur of colonial marvels and riches one cannot overlook the fact that these were at the expense of heavily exploited, highly-skilled labour without which none of the glory would have been possible. Cuba is full of these contrasts and you can easily get a taste of both worlds if you devote time to seeing and experiencing the two sides of colonialism. This guide is just an appetiser to give you a taste of some of the places you can visit to fully experience Cuba’s colonial heritage.


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