Classic Cuba


Culture | Festivals

Colonial cities, Cuban casas & the Caribbean coast

12 days £1,845 pp This is the per person group tour price, based on 2 sharing. The price is subject to change with exchange rate and flight cost fluctuations.
Dates & Prices


Wander the squares of Old Havana and enjoy a cocktail outside the iconic Hotel Nacional. Journey west to Vinales and watch how the world’s finest cigars are produced. Sip the best coffee in Cuba in the coffee region of Las Terrazas. In the south, visit the museum re-counting Cuba’s victory at the Bay of Pigs. Head into the lush mountains of Sierra del Escambray and encounter waterfalls and birdlife. In Trinidad, meander through the cobbled streets of Cuba’s most atmospheric town. Take a trip to the once-flourishing Sugar Valley and spend a day snorkelling in the clear waters of Playa Ancón. Finally, visit Santa Clara, where the iconic revolutionary, Ché Guevara, was reburied. Staying in delightful casas for most of your trip, you will experience the warmth of real Cuban life.

Special departure in November 2019 - Havana's 500th anniversary
Our Classic Cuba tour in November 2019 coincides with the 500th anniversary of the founding of Havana on 16th November, when great celebrations will take place across both the city and country. Enjoy joyous parades and live music by prominent Cuban artists as part of a very special holiday!


  • Colonial charm of Old Havana
  • Visit the historically significant Plaza de la Revolución
  • Rolling tobacco fields in the Viñales Valley
  • Coffee plantations in Las Terrazas
  • Eclectic architecture in Cienfuegos
  • Visit museum commemorating the Bay of Pigs invasion
  • Beautiful scenery and nature of the Sierra del Escambray
  • Cobbled colonial streets of Trinidad
  • Fascinating history of Cuba's sugar production in Valle de los Ingenios
  • Visit the mausoleum of the revolutionary leader, Ché Guevara

Places Visited

Havana - Viñales - Las Terrazas - Cienfuegos - Sierra del Escambray - Trinidad - Santa Clara

What's Included

Airport transfers
Ground transport with driver
Accommodation (casas)
Meals (refer to itinerary for meal plan)
Escorted English-speaking guide
Entrance fees to sites & parks
Itinerary & Map
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Day 1 : Havana

Arrive at Havana Airport where you will be greeted by a Travel The Unknown representative. Be transferred by classic car to your casa. Overnight in Havana.

Meal plan: n/a

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Day 2 : Havana

In the morning, take a walking tour of the Old Havana district, known for its pastel-coloured colonial buildings and its elegantly crumbling facades. Visit its enchanting plazas, including the beautiful neoclassical buildings in the Plaza de Armas and the baroque cathedral in the Plaza de la Catedral. After lunch, the rest of the day is free to explore Havana at your leisure. Stroll through Old Havana's cobbled streets, visit the Capitolio building in Central Havana, shop for revolutionary literature or stop off for a cocktail in a local bar. Overnight in Havana.

Meal plan: Breakfast

Founded in the 16th century by the Spanish, Cuba’s capital Havana became the springboard for the Spanish conquest of the Americas because of its strategic location. It is often seen as being three cities in one with Old Havana, Vedado and modern suburban districts. Old Havana boasts a variety of different Western architectural styles such as Baroque and Neo-Classical and different features such as palaces, fortresses and squares. Its buildings and fortress walls were declared a UNESCO World Heritage Site in 1982 and sit comfortably next to art deco and more modern styles.

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Day 3 : Havana

In the morning, take a walking tour of Vedado, the newer part of Havana. Visit the Plaza de la Revolución where some of Cuba's most important political speeches have taken place. The afternoon is free for you to explore Havana and stroll along the Malecón which faces out to Florida (only 90 miles away) or enjoy a rum cocktail at the famous Hotel Nacional de Cuba, where musicians reminiscent of Buena Vista Social Club perform on the terrace. Overnight in Havana.

Meal plan: Breakfast

Vedado developed in the 19th century, funded by the wealth generated from the sugar industry. The now crumbling houses were once a sign of wealth and opulence. In the district lies the Plaza de la Revolución where Castro made some of his most rousing speeches and the Malecón, which offers fantastic views over the sea. The famous Hotel Nacional, which was a favourite of mafia bosses and Hollywood stars alike in the 1940s and '50s, is found here and worth a visit.

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Day 4 : Havana - Viñales

Head towards the rolling tobacco fields of Viñales, stopping to admire the dramatic views of the Valle de Viñales, a UNESCO site nestled in the Sierra los Organos Mountains. After lunch, proceed to the Cueva del Indio, the largest cave system in Cuba. Take a boat ride through the cave and observe some fascinating rock formations close up. The rest of the day is free to spend exploring Viñales and the surrounding area, or relaxing at your leisure. Overnight in Viñales.

Meal plan: Breakfast

Surrounded by limestone hills known as mogotes, the picturesque Viñales valley is a UNESCO World Heritage Site. The local farmers still use traditional agricultural techniques to grow tobacco and the area has its own unique culture that is preserved through its architecture, crafts and music. Caves are nestled within the slopes of the mogotes, which were inhabited before the Spanish arrived, and the valley is home to endemic flora and fauna such as the Mountain Palm, the bee hummingbird and the Cuban tocororo. 

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Day 5 : Viñales

Walk through the tobacco fields and watch the sunrise. Stop off at a local tobacco farmer's home to see first-hand how cigars are made before returning to your casa for breakfast. The rest of the day is free to explore your surroundings by foot, or try your hand at horse riding, which can be arranged by the guide. Overnight in Viñales.

Meal plan: Breakfast

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Day 6 : Viñales - Las Terrazas

Drive to Las Terrazas, Cuba's most successful eco-tourism centre. Take a stroll through your surroundings then dine at a restaurant that offers wonderful views over the surrounding landscapes and wash it down in the small café next door with some of the best coffee in Cuba. Afterwards,embark on a soft trek along the area's many walking trails or go birdwatching. If you're lucky, you may spot Cuba's national bird, the tocororo, as well as other small songbirds and nightingales. Evening free. Overnight in Soroa.

Meal plan: Breakfast

Designated as a bio-reserve by UNESCO, the small community and nature reserve of Las Terrazas is nestled in the Sierra La Rosario Mountains. The reserve covers 5000 hectares of forest which was planted on the deforested hills by building terraces to avoid erosion. The forest includes lakes, rivers and waterfalls and is rich in a wide variety of flora and is home to 117 bird species. It was part of a reforestation project thought up by Castro to help improve the life of the impoverished residents in the area.

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Day 7 : Las Terrazas - Cienfuegos

In the morning, leave for Cienfuegos, driving through many citrus fruit and sugar plantations on the Zapata Peninsula. On the way, stop at Cueva de los Peces, a large sinkhole containing hundreds of multi-coloured fish. Continue on to Playa Girón and visit a museum dedicated to Cuba's victory during the infamous Bay of Pigs invasion. Drive on to Cienfuegos and check into a casa close to Punta Gorda. Evening is free to spend as you wish. Overnight in Cienfuegos.

Meal plan: Breakfast

Cuba's ‘Perla del Sur’ (Pearl of the South), Cienfuegos was officially founded in 1819 by Frenchman Don Louis de Clouet and the influence the European settlers had on the city is still clearly evident to this day. The historic old town, cited as an outstanding example of 19th century urban planning, is listed as a UNESCO World Heritage site.

The Bay of Pigs Invasion was a botched attempt to overthrow the Cuban Communist government. Since the Cuban Revolution in 1959, Castro became increasingly antagonistic towards the US who saw his close relationship with the Soviet Union as a threat to their interests. After many failed attempts to usurp Castro, on 17th April 1961, CIA trained Cuban exiles landed at the Bay of Pigs armed with American weapons. It was hoped that the exiled force would act as a rallying point for Cuban Citizenry. However, the plan quickly fell apart as the exile force was met with an unexpected Cuban counter-attack and the small Cuban air force sank their supply ships. As a result, 100 soldiers were killed, over 1,100 captured and the uprising never happened. This failure cost the US dearly as Castro used the attack to solidify his power and requested Soviet aid which eventually sparked the Cuban Missile Crisis. It also affected US relations with other countries in Latin America as Castro was now considered a hero for standing up to US interference and imperialism.

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Day 8 : Cienfuegos - Sierra del Escrambray - Trinidad

Morning sightseeing tour of Cienfuegos. The focus of the tour is the city's main square Parque Marti, recently declared a UNESCO Heritage Site, which is surrounded by the impressive Palacio del Ayuntamiento, the elegant Italian-style Teatro Tomas Terry and the neo-classical cathedral. Stroll through the bustling Paseo del Prado, which is lined with colonial buildings and shops. You may also hear music from Benny Moré, Cienfuegos' most famous musician, being played on the public speakers. 

Leave for the tropical mountains of Sierra del Escambray, just 30 minutes from Cienfuegos. Enjoy lunch then take a soft trek (2-3 hours) around El Nicho, home to beautiful waterfalls and natural lagoons. Pack your swimwear and towel, in case you decide to take a dip in one of the lagoons (note, water is cold). Look out for endemic birds and enjoy panoramic views of the lush green mountains. In the late afternoon, depart for Trinidad. The evening is free to stroll around the cobbled plazas of Trinidad. Overnight in Trinidad.

Meal plan: Breakfast

The Sierra del Escambray is a mountain range located in central Cuba. Pico San Juan, the range’s highest peak, stands at 960 metres above sea level. Popular sites include the stunning El Nicho waterfall, the Topes de Collantes Natural Park with waterfalls, caves, rivers and canyons and the Valle de los Ingenios, which formed the epicentre of Cuba's sugar trade in the 19th century. From 1960-62, the mountains provided the backdrop to the War against Bandits and were the planned refuge during the Bay of Pigs Invasion. 

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Day 9 : Trinidad and the Valle de los Ingenios

Morning walking tour around Trinidad, a justifiable UNESCO Heritage Site, with a charming colonial central plaza, a cathedral and pastel-coloured buildings that line the cobbled street. In the afternoon, visit the Valle de los Ingenios, where sugar was produced until the late 19th century. Climb the watch tower for panoramic views of the stunning landscape. Stop off at other vantage points and at the local pottery-making workshop where you can buy handicrafts. Return to the centre of Trinidad. The evening is free for you to spend at your leisure. Overnight in Trinidad.

Meal plan: Breakfast

Founded in 1514, Trinidad prospered from the sugar trade in the 19th Century. Set between the Escambray Mountains and the beautiful Caribbean coastline, the city was made a UNESCO World Heritage Site in 1982. Its architecture is a mix of 18th Century Moorish and Andalusian influences and 19th Century European neoclassical forms. The irregular pattern of the city’s squares and cobbled streets make it a great city to explore. It is a perfectly preserved example of a Spanish colonial settlement with its illustrious colonial style mansions full of Italian frescoes, wedgewood china and French chandeliers which hark back to the city’s heyday.

The UNESCO World Heritage Site of Valle de los Ingenios (Valley of the Sugar Mills) comprises three valleys about 12 kilometres (7.5 mi) outside Trinidad. The valleys - San Luis, Meyer and Santa Rosa - formed the centre of Cuba's sugar production from the late 18th century until the late 19th century. At its peak, there were over fifty sugar mills in operation across the valleys, with over 30,000 slaves working in the mills and the surrounding sugar cane plantations. With the abolition of slavery, sugar production declined and many of the mills fell into disrepair, but some have been carefully preserved and provide a fascinating insight into Cuba's Colonial-era slave trade.

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Day 10 : Trinidad

Free day in Trinidad. Options to explore more of the city or take a local taxi to nearby Playa Ancón (11 km). It is a beautiful stretch of white sand with some of the best diving and snorkelling on the island. Overnight in Trinidad.

Meal plan: Breakfast

Located near the city of Trinidad, Playa Ancón is a tourist only beach that boasts nearly 6 kilometres of white sand which is ideal for relaxing on. The beach is also a hotspot for swimming, snorkelling and scuba diving. It has 21 scuba-diving sites where you can see concentrations of black coral, sponges, common sea fans and a wide variety of other colourful fish.

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Day 11 : Trinidad - Santa Clara - Havana

After breakfast leave for Santa Clara (2.5 hours), home to Ché Guevara's Mausoleum, where the Latin American hero was re-buried. Learn about his influence on Cuba and why he is so revered. After lunch, continue the drive to Havana (3.5 hours). Your final evening in Cuba is free spend as you wish. Overnight in Havana.

Meal plan: Breakfast

Located in the heart of Cuba, Santa Clara was founded in 1689 by citizens of the coastal city of Remedios, who wanted to escape regular pirate attacks. One of the city's famous former inhabitants was the philanthropist, Marta Abreu de Estévez, also known as the Benefactress of the city. Wishing to improve the lives of Santa Clara's citizens, Marta Abreu donated large sums of money to the city, and her influence can still be seen throughout Santa Clara today; an asylum, several schools and a theatre still stand. The city is most well-known as the final resting place of Ché Guevara, who captured Santa Clara during the final battle of the Cuban Revolution in 1958, toppling Batista's regime.

Ernesto 'Ché' Guevara was a revered and controversial historical figure. Born in Argentina, he became radicalised when, as a medical student, he witnessed the terrible poverty, hunger and disease during his travels around South America. This fused with his interest in Marxism and he realised that the only way to solve South and Central America's problems was through armed revolution. In 1954, he travelled to Mexico, met Fidel Castro and joined his 26th July Movement. He played a key role in the guerrilla war against the Cuban dictator Batista, capturing Santa Clara in the final battle of the revolution and toppling the dictator's regime. He guided the country towards a friendship with the Soviet Union which, thanks to US sanctions, damaged Cuba's economy and, along with some unsuccessful reforms, caused him to fall out with Cuba's leaders. He left the country in 1965 to spread revolution to parts of the developing world. After an unsuccessful guerrilla campaign in the Congo, Guevara travelled to Bolivia to lead forces fighting against the government. He was captured with the help of the CIA and executed on 9th October 1967. His remains were exhumed in 1997 and reburied in Santa Clara. During his life, Ché Guevara was a prolific writer and wrote a manual on guerrilla warfare as well as a memoir of his time travelling as a student. Today, he is still a hero in Cuba and has become a worldwide symbol of anti-imperialism and revolution. His image has become a commodity over the years and is found on an endless array of items that contribute to the consumer culture that he hated.

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Day 12 : Departure

Transfer at an appropriate time to the airport for your return flight.

Meal plan: Breakfast


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Colonial cities, Cuban casas & the Caribbean coast


Our trip to Cuba was well arranged with a thoughtful collection of places and experiences to maximize our understanding of the country. Travel the Unknown arranged accommodations that were unique, giving us wonderful opportunities to experience Cuban family life.

Duncan & Nora Etches , Eastern Cuba Explorer, Cuba

Travel the Unknown offered us an excellent itinerary, clearly and competitively priced without any surprises or changes. Staff were very helpful and ensured we had all the necessary information. Will be first port of call for any holiday on their list. Unreservedly recommend.

Winston Peters , Tailormade Cuba

My husband and I have traveled to many different countries, usually not on tours. After talking to several friends who used Travel the Unknown, we contacted them to arrange a private tour for 2 families. They were extremely helpful and responsive. One example of this was our adding a few things to the tour as they originally had it. Also, during the trip, when we decided together to skip something that was originally planned, our guide was fine with it. When any of us emailed the company with questions, we heard back immediately, taking the 6 hour time difference into consideration. We will definitely book again with Travel the Unknown.

Pollans family , Tailormade Cuba

Our Cuba tour was unforgettable! Historic Havana, classic cars, vibrant music scene, colonial towns, stunning tobacco country, lovely beaches, comfortable lodging, delicious food and, most importantly, an outstanding guide who introduced us to the complex history of this gorgeous island. The warmth and friendliness of the people was moving, and we came home with valuable new perspectives too.

Barbara Kelley , Tailormade Cuba
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