Eastern Cuba Explorer



Colonial gems, diverse culture and raw natural beauty

15 days £2,295 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


Eastern Cuba is an intoxicating mix of vibrant culture, colonial history and raw natural beauty. Starting off in Havana, explore Cuba's fascinating, crumbling capital, before heading to the city dubbed the 'Pearl of the South', Cienfuegos, and on to the picturesque colonial town of Trinidad. Visit Camagüey`s hidden colonial churches and museums, then head east to the energetic city of Santiago de Cuba to uncover its Afro-Caribbean culture. Next, stop off in Guantanamo on your way to the rugged shores of Baracoa, where you will visit the Spanish forts that once protected Cuba’s oldest city and sample the most exotic cuisine in Cuba. Return inland as you visit the city of Holguín and the nearby paradisaical Playa Guardalavaca. Finally, visit the city of Santa Clara and the resting place of revolutionary figure Ché Guevara before returning to Havana.

Special departure in November 2019 - Havana's 500th anniversary
Our Eastern Cuba Explorer 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, including in the former capital of Santiago de Cuba. Enjoy joyous parades and live music by prominent Cuban artists as part of a very special holiday!


  • Visit the historically significant Plaza de la Revolución
  • Colonial charm of Old Havana
  • Eclectic architecture in Cienfuegos
  • Cobbled colonial streets of Trinidad
  • Fascinating history of Cuba's sugar production in Valle de los Ingenios
  • Camagüey's labyrinth of winding alleys
  • Afro-Caribbean culture of Santiago de Cuba
  • Rugged coastal scenery of Baracoa
  • Visit Che Guevara's mausoleum in Santa Clara

Places Visited

Havana - Cienfuegos - Trinidad - Ciego de Ávila - Camagüey - Bayamo - Santiago de Cuba - Guantanamo - Baracoa - Playa Guardalavaca - Santa Clara

What's Included

Arrival & departure transfers
Ground transport with driver
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 in Havana airport where you will be greeted by a Travel The Unknown representative and 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 façades. Visit the some 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, make a classic car tour to see main attractions of Havana. You will see beautiful neighbourhoods such as Vedado, Nuevo Vedado and Miramar. Places you will visit during the tour include the Plaza de la Revolución, where some of Cuba's most important political speeches have taken place, the Malecon, which faces out to Florida (only 90 miles away), the beautiful 5th Avenue in Miramar and the famous Hotel Nacional de Cuba, where you may have the chance to see musicians reminiscent of Buena Vista Social Club perform. 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.

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 3 : Havana - Cienfuegos - Trinidad

Early departure to Trinidad with a stop for lunch (not included) and sightseeing in Cienfuegos, the 'Pearl of the South'. Arrive in Trinidad in the afternoon, and the rest of the day is free for you to explore at leisure. Overnight in Trinidad.

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.

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Day 4 : Trinidad

After breakfast, visit the Valle de los Ingenios. Climb the watch tower for panoramic views of the stunning landscape. Stop off at other vantage points and the local pottery-making workshop where you can buy handicrafts. In the early afternoon, return to the centre of Trinidad. The rest of the day is free to relax or explore. 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 5 : Trinidad

Today is free at your leisure, with options to explore more of the city or take a local taxi to nearby Playa Ancón (11km). 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 6 : Trinidad - Ciego de Ávila - Camagüey

After breakfast, leave for Camagüey. Stop en-route at Ciego de Ávila for lunch, arriving early afternoon in Camagüey. The evening is free to rest. Overnight in Camagüey.

Meal plan: Breakfast

Founded in 1840, the city of Ciego de Ávila is in the central part of Cuba. It is a major centre for commerce and transportation for the surrounding agricultural lands. Sugarcane is the main commodity although tropical fruits, beeswax, honey and molasses are also produced. It is regarded as the most modern of Cuba’s provincial capitals and the famous pop-artist Raúl Martinez was born there. Much of the city’s neoclassical architecture was commissioned by the widowed socialite Angela Hernández, viuda de Jiménez, who fought to create a cultural hub in her hometown.

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Day 7 : Camagüey

Enjoy a half-day walking tour in Camagüey where you will explore its maze-like streets, around the corners of which lie hidden churches and squares. The rest of the day is free. Overnight in Camagüey.

Meal plan: Breakfast

Camagüey is the third largest city in Cuba. It’s a labyrinth of winding alleys and forked streets which, according to local legend, was to defend the city against pirates and raiders. A more practical, and far less exotic, reason is that the city developed without proper planning. Camagüey’s historic centre is a UNESCO World Heritage site.

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Day 8 : Camagüey - Bayamo - Santiago de Cuba

Drive to Santiago de Cuba, stopping en route for lunch in the city of Bayamo (not included). On arrival in Santiago, the rest of the day is at your leisure. Overnight in Santiago de Cuba.

Meal plan: Breakfast

The easterly city of Bayamo is considered the Cradle of Cuban Nationality; the first sparks of the Cuban revolution against Spain were ignited here in the 19th century. The capital of the Granma province, Bayamo pre-dates both Havana and Santiago de Cuba, and the sense of history here is palpable; a large number of residents still use a horse and cart as their principal mode of transport.

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Day 9 : Santiago de Cuba

Enjoy a half-day tour of Santiago de Cuba, during which you will see the Moncada barracks and the imposing fortress of Castillo del Morro. The rest of the day is free for you to explore at your own pace. Overnight in Santiago de Cuba.

Meal plan: Breakfast

Santiago de Cuba was founded by the Spanish in 1514 and experienced an influx of French immigrants coming from Haiti in the late 18th Century. This French influence added to the eclectic mix of African and Spanish cultures already thriving in the city. The city was the launch pad of Fidel Castro’s nationalist Revolution. Santiago de Cuba was the hometown of the poet Jose Maria Heredia and is a major hub for culture and the arts. Its famous for its traditional dances such as guaguanco and son, from which salsa is derived. The citadel is a UNESCO World Heritage Site for being the best example of Spanish-American military architecture. 

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Day 10 : Santiago de Cuba - Guantanamo - Baracoa

After breakfast, set off for Baracoa, a wild rugged town set on Cuba's eastern tip. Stop in Guantanamo en route, now more famous for the controversial US Naval Base. After a short tour of Guantanamo, continue the journey to Baracoa and check in at the casa. The evening is free at your leisure. Overnight in Baracoa.

Meal plan: Breakfast

Although it is famous for its US navy base, Guantanamo’s landscape is one of contrasts; thick rainforests in the north, and dry arid land in the south. The Nipe-Sagua-Baracoa Mountains dominate the region, dividing the climate. The north coast is battered by winds and is the wettest part of the country whilst the south is dry and sheltered and the hottest.  The province is 80 kilometres away from Haiti at its closest point and is close enough to see the lights of Haiti on a clear night. The province receives a high number of Jamaican immigrants and much of the architecture is comparable to the French Quarter of New Orleans making Guantanamo a place unlike any other in Cuba.

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Day 11 : Baracoa

In the morning, go on a walking tour of the city. The rest of the day is free to explore at your leisure. Overnight in Baracoa.

Meal plan: Breakfast

Baracoa is the oldest Spanish settlement in Cuba and was the country's first capital. It is located on the spot where Christopher Columbus first landed on his first voyage to Cuba and is the only place where the descendents of the indigenous Taino still live. The table-topped hill, El Yunque, looms over the city and the cobbled streets are lined with carnival-coloured one story buildings. Cocoa is grown in the surrounding region and the city is famous for its white chocolate. The geographical isolation makes it an ideal destination for those looking to get away from the busier places that are typically popular with tourists. 

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Day 12 : Baracoa - Playa Guardalavaca - Holguín

Early morning departure to visit the Parque Nacional Alejandro de Humboldt on the way to Holguín. Stop for lunch at Playa Guardalavaca, where you will have some time to relax and enjoy one of the most beautiful beaches in Cuba. Arrival to Holguín in the afternoon. Overnight in Holguín.

Note: You may choose between beach time at Guardalavaca or visit some of the attractions in Holguín.

Meal plan: Breakfast

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Day 13 : Holguín - Camagüey - Santa Clara

Early departure from Holguín to arrive in Camagüey in time for lunch. Arrive in Santa Clara in the late afternoon, where the rest of the day is free for you to explore at leisure. Overnight in Santa Clara.

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.

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Day 14 : Santa Clara and Ché Guevara's Mausoleum

After breakfast, visit the main sites of Santa Clara, including Vidal Park and 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, depart for Havana for your final night in Cuba.

Meal plan: Breakfast

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 15 : Departure

Transfer to the airport for your flight home or choose to extend your trip. 

Meal plan: Breakfast


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Classic Car Journeys (1-14 days)

Travel in style along Cuba's historic roads in a classic American sedan

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Axes Apart: Iran & Cuba (16 days)

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Eastern Cuba Explorer (15 days)

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Classic Mexico & Cuba (15 days)

Discover the highlights of two Latin gems

Essential Cuba & Colombia (14 days)

Experience two of Latin America's most vibrant cultures

Classic Cuba (12 days)

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

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

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

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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