Custom Cross-Country Cuba Tour

Cuba Coast-to-Coast Tour

Explore Cuba from east to west - from Santiago to Havana for
10D/9N Starting at $4690 per person

This 10-day cross-country tour of Cuba starts in Santiago de Cuba, closer to Jamaica than Havana, then travels high into the Sierra Maestra mountains for a stay at Villa Izlazul Santo Domingo.

From here you can take hikes and horseback rides along the trails and visit Fidel Castro and Che Guevara's hangout  at Comandancia de la Plata.  An overnight stay in Camaguey includes a colonial city tour.

havana prado street

Spend two nights Trinidad with a city tour, jeep safari in the Escambray Mountains, tour of the local sugar plantation ruins. The drive to Havana includes a stop in Santa Clara and the Che Memorial. Three nights in Havana with a colonial city tour and our Hemingway tour.

  • Cuba Coast-to-Coast Tour Highlights:
  • Santiago de Cuba
  • El Morro Fortress
  • Comandancia de la Plata - Fidel & Che's Hangout
  • Camaguey
  • Trinidad & the Escambray Mountains
  • Santa Clara - the Che Memorial
  • Havana

Suggested restaurants for lunches and dinners are included in each city as well as suggested venues for live music and cocktails. 

*Restaurants, bars and music clubs are only suggested. Reservations can be made but all bills are to be paid directly.


Lost World Adventures itineraries can be tailor-made according to your plans and preferences: budget, hotel selections, travel dates, optional excursions, length of trip, etc.

Day 1:  Santiago de Cuba

You will be met at the Santiago de Cuba Airport and transferred to your hotel.

All transportation will be by luxury car or van with a private English-speaking guide-driver. Your tours will be delivered by experts. One bottle of mineral water per person, per day will be provided.

Overnight Casa La Hiedra, breakfast included – 2 nights.               

Casa La Hiedra is located in the residential area of Santiago de Cuba, covered by ivy, with extraordinary spaces. Seventeen years of experience in a personalized and excellent service in an atmosphere of comfort and familiarity, favored by a full tranquility and good taste, with abundant and large spaces: main hall, portal, terrace, garden, patio and mirador-roof.

The Library room brings one of the most comprehensive collections of Cuba's history, including the period of the Revolution. The library also has a TV. They offer 4 rooms with private bathrooms and king-size beds, garden windows and abundant natural light; individualized dinners with organic products, city tours, beach and mountain, Spanish classes, history, culture, and Cuban dance, massage, garage, cab, washing and ironing clothes.

El Morro Fortress            

You will visit the Morro Fortress for sunset. The Morro Castle or the San Pedro de la Roca Castle is a fortress declared a World Heritage Site by UNESCO in 1997 for being the most complete and the most preserved example of Spanish-American military architecture, based on the principles of Italian and Renaissance styles.

It constituted the defensive system of the eastern part of the country against corsairs and pirates. Visit of this historical site with a panoramic view of the Bay of Santiago. 

*Suggested dinner reservations - St. Pauli             

In a city of no great culinary tradition, St Pauli arrived like a hurricane. Walk the long mural decorated corridor off Calle Saco to a bright room featuring blackboard menus and a glass-wall kitchen. Everything is consistently good, particularly the cocktail glass gazpacho, pulpo al ajillo (octopus with garlic) and pineapple chicken fajitas. 

*Suggested - Live Music at Casa Granda Rooftop  

Day 2: Santiago City Tour         

Visit the main historical and cultural places of the urban historic center of the city, which was declared National Monument on October 10, 1978. Visit the Moncada Barracks and its museum of July 26, the Revolution Square and other historical, religious and cultural sites and enjoy a sit in the Cespedes Park.

*Suggested lunch reservations - La Brassa             

Genuine Creole and international cuisine in an elegant and comfortable atmosphere. 

Church Of The Virgen De La Caridad Del Cobre  

Visit the Church of La Virgen de la Caridad del Cobre, dedicated to Cubas patron saint. Learn the mystic story of the Virgen de la Caridad, climb the hill to the Cimarron monument which is a sculpture created in bronze and iron to honor one of the earliest slave revolts that took place in the country. Up there, you will also have the opportunity to enjoy a beautiful view to the blue lagoon.

*Suggested dinner reservations - Palenquito       

Barbecue is the specialty of this casual backyard restaurant on the outskirts of Santiago. Grilled pork and chicken are served with the typical sides, but the real star is dessert. Try rich zapote or coconut ice cream in the shells of the original fruit. Portions are huge, but you suddenly might not want to share. 

*Suggested - Music at Casa de la Trova. Check out the local music scene with traditional Son bands and Trovadors. 

Day 3:  Santiago - Villa Santo Domingo

Transfer Santiago to Villa Santo Domingo.  Distance - 120 miles. Driving time - around 2.5 hours.

Overnight Villa Santo Domingo, breakfast included.        

High in the Sierra Maestra mountains is a picturesque tourist villa promising a pleasant stay to all visitors: Villa Izlazul Santo Domingo. Situated along the Yara River, from its cabanas it is possible to hear the rushing of the river and the melodious chirping of birds. You can enjoy mule and horseback riding, hikes and walks along trails of historical and natural interest and beauty.

Santo Domingo is also the venue of lively guateques (Cuban countryside fiestas) where the typical music of the region enraptures its listeners. To witness the traditions, way of life and customs of the farmers living in Cuba's eastern mountains is an extraordinary experience. Coffee growing represents the area's main activity.

Visitors can trek along the banks of the Yara River or they can hike the Pico Real del Turquino the highest point in Cuba, 1,974 meters above sea level, accompanied by specialized guides. Located 24 km south of Bartolome Maso.

Day 4: Villa Santo Domingo - Camaguey / Fidel's Hangout + Colonial Camaguey City Tour

Comandancia De La Plata - Fidel's Hideout           

A 2-3 hour gentle hike through the Sierra Maestra mountains to reach Fidels hideout - the organizing and staging post for the Cuban revolution. Visit the completely preserved huts where Fidel and Che Guevara led the group of revolutionaries to ultimate victory in the Cuban revolution. And if revolutionary history is not your thing, the views alone are worth the hike with spectacular scenery and crisp, fresh mountain air. Wear hiking boots or shoes.

This afternoon you will transfer to Camaguey.  Driving time - around 4.5 hours.

*Suggested lunch reservations - 1800      

Classic private restaurant located in the centre of the architectural Church and Hospital of St. John of God. Here you can taste various dishes of Cuban food, made by Chef Miguel Ricardo that include a variety of tapas, seafood, fish, beef, pork, rabbit, mutton, chicken, etc. Not included - to be paid locally.

*Suggested lunch reservations - El Paso  

A private restaurant with all-day hours, plus a funky interior and an enviable Plaza del Carmen location. There's flavorful ropa vieja (spiced shredded beef), heaping bowls of arroz con pollo a la chorrillana (chicken, rice prunes and peppers in a ceramic bowl). Try pan patato for dessert – consisting of cassava and coconut. Not included - to be paid locally.

Colonial Camaguey City Tour      

Camagueys historic center is considered the largest as well as the best preserved on the island has been designated a UNESCO World Heritage Site. Visitors delight in, or are intrigued by, the city's many lavish churches and the twisted maze of streets, formerly designed to confound marauding pirates.

Camaguey is the birthplace of former Cuban National Port Nicolas Guillen and the home of the world-renowned Ballet de Camaguey. It is full of charming cobblestone plazas, historic statues and intriguing museums. You will find plenty of tinajones (earthenware

jars) decorating the streets. The people of Camaguey originally produced the jars to collect rainwater during a drought. Today, they are one of the city's decorative hallmarks.

Overnight Encanto La Sevillana, breakfast included.         

In a gorgeous 1920's mansion decked with stained glass and chandeliers. Great spaces include a huge courtyard with a fountain and a rooftop terrace with hot tubs. Compared to all this, rooms are less impressive, though adequate. There's a small on-site restaurant.

Day 5: Camaguey - Trinidad / Trinidad City Tour

After breakfast this morning you will transfer to Trinidad.  Driving time - around 4.5 hours.

Overnight Finca Kenia, breakfast included – 2 nights.     

Finca Kenia is one of the oldest houses in Trinidad, built in the second half of the 19th-century on the edge of Santa Rosa Valley. It has spacious rooms, with a stylish, modern design within a natural and rustic setting.

The large garden and back yard looks out on the ruins of a colonial fort. Each room is air-conditioned and is en-suite and has a pretty private sitting area outside the front of the room with table, chairs, rocking chairs and sometimes even a hammock. Hotel facilities include swimming pool and restaurant (serving breakfast, lunch and dinner).

*Suggested lunch reservations - San Jose              

The latest paladar in Trinidad, San Jose has a Cuban-Fusion inspired menu. Its fresh, tasty and comes in huge portions! The decoration is part New York loft, part Cuban colonial home with a mixed clientele of Cubans and Tourists. There is an air-conditioned section for those who need to cool down.           

This walking tour offers you an introduction to Trinidad, a UNESCO world heritage site. Your local expert guide will talk you through the history of the town by visiting its architectural high points and give you some insight into its complex history both in the colonial period and in the years after the revolution.

Wear comfortable shoes, as although quaint, the cobbled streets are not for heels.

*Suggested restaurant reservations - La Redaccion           

A seafood restaurant and bar in a traditional colonial house from the 1800s. The owners have lived in Europe and mix a traditional Cuban menu with European influences. The focus is fresh fish caught daily, along with organic meat and vegetables from local farms, fishermen and suppliers.

The food speaks for itself: uncomplicated but prepared exceptionally well. La Redaccion has history, a great vibe, delicious food, rum drinks, live music.

*Suggested - Live Music at Bar Colonial   

Every night except Fridays, the best band in Trinidad, Aire Fresco, jams away to the delight of sitting down customers and passersby. Old Cuban classic, blues and jazz, you name it, they got it.

Day 6: Topes de Collantes / Sugar Plantation Ruins and Slave History Tour

The great natural park Topes de Collantes is situated between Playa Giron and Trinidad. It's a place of extraordinary beauty and of great scientific value for Cuban botany, zoology and ecology.

This protected area of 200 square kms has a great number of endemic flora and fauna. On this tour you'll ride up to the Escambray Mountains in 4X4 SUVs. 

You will go up to Guanayara and hike through the tropical forest of Topes. Bird watching and an opportunity for swimming at the waterfall make this a must for nature lovers. (Remember to to bring your swim suit, mosquito repellent and water).

*Suggested lunch reservations - La Marinera        

A favorite with the locals! Great seafood, though the menu includes meat and chicken as well. Do not miss the house special, seafood rissotto (Arroz a La Marinera). Beware, the portions are huge.

Tour the local sugar plantation ruins to understand slave history in relation to the 19th-century sugar industry. See slave quarters and learn about the enormous impact sugar had on this area. See plantation homes of the sugar barons. Some have been exquisitely restored.

*After dinner suggestion - Dancing at Casa de la Musica and Casa de la Trova        

Have coffee, a refreshing drink, or a chocolate fondue at this elegant private restaura

Day 7: Transfer to Havana via Santa Clara with Che Memorial      

You will be transferred from Trinidad to Havana, making a stop in Santa Clara en route.   

Santa Clara is Revolution Central, because the Battle of Santa Clara was key in the revolutionary war of 1958. The main attraction is the Plaza de la Revolucion, with monuments inscribed with Che's rousing rhetoric.

Also in the square is a small, moving museum dedicated to Che Guevara's life and works, and below it, an eternal flame dedicated to Che and 16 of the fighters from his failed 1967 Bolivian campaign.

Another significant monument is El Monumento a la Toma del Tren Blindado, where the rebels derailed a train full of government troops (see Che Part I starring Benicio del Toro for the cinematic version). If this is the only provincial colonial town you plan to visit, do make time to wander the streets, typically Cuban and unspoiled, and soak up the local atmosphere.

Santa Clara is non-descript compared with the prettiness of Cienfuegos or Trinidad, but it's nonetheless a pleasant place to wander. Parque Vidal is a focus for gatherings of young and old alike, and nearby, the Museo de Artes Decorativas with its exquisite colonial relics: chinoiserie screens, ornate furniture, escritoires and English china, speak of a jewel-encrusted, distant past.                 

Che Memorial  

No trip to Cuba is complete without a trip to the Che memorial. Pay homage to this charismatic leader of the Cuban revolution where he fought and won the battle of Santa Clara.

*Suggested - Cafe Museo Revolucion      

This new cafe pays homage to Santa Clara's (and Cuba's) revolutionary past with photos, old uniforms and other ephemera lovingly curated by the owner. The coffee and milk shakes are pretty revolutionary too.

Overnight Gran Hotel Manzana Kempinski, daily breakfast included – 3 nights.  

The Gran Hotel Manzana Kempinski La Habana, originally built between 1894 and 1917 as the first European-style shopping arcade in Cuba, is situated in the heart of the old Havana with a direct view of the Capitol and the Great Theatre of Havana and amidst UNESCO World Heritage sites. The famous Castillo del Morro is accessible within a 10 minute drive.

Experience the first true luxury hotel in Cuba and indulge yourself while staying in one of the 246 large rooms or suites with extra high ceilings and French windows opening out to the old city.

Hotel facilities include a variety of restaurants and bars, a one of a kind cigar lounge and a roof top Panoramic Restaurant and Bar with spectacular views over the old city. Relax in the spa, fitness center and rooftop pool.

*Suggested - drinks at El del Frente          

El Del Frente means the one in front. The menu is similar to that of OReillys, one of the best ceviches tacos and tatakis in town. El Del Frente has a rooftop terrace/bar where you can either sit for a drink and a cigar, or have a light informal dinner surrounded by Old Havanas historic architecture. The drinks here are exceptional.

*Suggested dinner reservations - La Guarida        

Enrique and Odeisys Nuñez first opened what has become Cuba's most celebrated paladar on July 14, 1996. Anyone who has been to La Guarida will find it difficult to disagree that Enrique and Odeisys have managed to create their own magical place. Dinner reservations at 7:30pm or at 9:00pm.

Day 8: Colonial Havana City Tour / Hemingway Tour       

Walk in the footsteps of Havana´s colonial past visiting the four key squares of Old Havana, a UNESCO world heritage site. Visit Plaza de Armas, Plaza San Francisco de Asis, Plaza Vieja and Plaza de la Cathedral with our expert guide offering insightful history along the way. This is a walking tour and takes approximately 2 hours.

*Suggested lunch reservations - Doña Eutimia     

An elaborate ambiance, a fresh and functional design and a privileged location are attributes that allow this restaurant to offer both comfort and very good Cuban creole food. Situated in the heart of Old Havana just off the cathedral square. Reservations are essential.       

Gertrude Stein, the celebrated American writer, once said that Ernest Hemingway had a good nose for finding good places to live and eat. She wasn’t wrong at all, as Hemingway’s villa on the outskirts of Havana proves.

Located on a hill and surrounded by lush tropical vegetation and a magnificent view of the city in the distance, the house was visited by numerous renowned celebrities during the 1940s and ´50s. Today it is exactly as Hemingway left it in 1960, with hundreds of personal belongings, large swimming pool, the Wheeler boat he used for fishing, the three-story tower with its spectacular views and much more.

Your expert guide, a retired professor of English literature at the University of Havana, will show you around and share with you interesting insights into the life of Hemingway and that period in Cuban history. 

On the way back to town, your guide will bring you to see the Cojimar fishing village: a small picturesque town that inspired Hemingway to write the novel 'The Old Man and the Sea', and whose fishermen he dedicated his Nobel Prize to. 

As you finish the tour you will have an opportunity to see some of the most spectacular views of the city from the El Morro fort across the harbor from Havana. This tour takes approximately 4 hours and is done in a convertible classic American car from the 1950's.

*Suggested dinner reservations - Tierra, Cuban Art Factory           

New restaurant inside Fabrica de Arte Cubano (Cuban Art factory). Travelling-themed, the menu is a culinary tour of the world, with 20 delicious dishes. Drinks are delicious and huge.

*Suggested - Music at Fabrica del Arte    

A meeting place for artists and avant-garde arts. Enjoy music, dance, film, art and shows under the same roof. Prices are reasonable making it accessible to some Cubans.  Beat the crowd: For a fee of US$16, we can secure your entrance bypassing the queue crowds after 10pm.

Day 9: Food Tour and lunch at Grados / Art Tour (2 studios)

With your chef, you will visit a produce market and a store to learn about the different ways (and prices) Cubans have access to food. Then lunch a Grados, a return to old school paladars where the owner is the chef. Raulito chats as he cooks while you enjoy a drink.

Expect long lost childhood recipes from pre revolution Cuba such as the delicious lamb slow-cooked in pru (an eastern Cuba herbal drink) or a countryside classic called farm eggs on a bed of maize. Lunch is included.        

You will visit 2 Cuban artists in their studios. Get behind the facade and interact with this thriving community depending on your particular interest. Photography, sculpture or painting. Specify whether you would like to see well known or up and coming artists.

*Suggested dinner reservation - San Juan              

San Juan is a lovely restaurant with a traditional wooden oven and stove. One can experience the traditional flavors of Cuban cuisine with the right touches of contemporary looks and ingredients combinations. Great atmosphere with live music and fantastic service.

*Suggested - Tropicana Cabaret 

Opened in 1931 the Tropicana has played host to Benny More, Nat King Cole, Jack Nicholson and 'Lucky' Lucian and many more. This is a Vegas-style extravaganza with seating for 1,400 people and 10 performers going through the full range of popular Cuban dance.

As you'd expect the dancers are beautiful and the costumes, choreography and routines are excellent, but the food is poor, the show lasts forever and it is seething with tourists. A recent revamp seems to have changed everything and nothing with the basic formula remaining as it has been for years.

Day 10: Int'l Departure

You will be transferred to the airport in accordance with your int'l departure time. 


Price from $4,690.00 per person, based on double occupancy
Days 10
Nights 9
  • Accommodations with breakfast
  • Private transportation in luxury vehicle
  • Private English-speaking driver/guide for days 1-7
  • Private guided excursions
  • Concierge services
  • Int'l airfare
  • Lunches & Dinners
  • Guide/driver tips

"Incredible experience. Easy planning. Would use them again if we wanted to travel to one of their other service areas."

All of our accommodations were first rate! Each one completely unique, beautifully decorated and unbelievably comfortable. Our guides were very fluent in English, supremely organized, and superbly knowledgeable. We learned so much about the sites and the area. I'm so inspired that I intend to do more study. We couldn't have asked for better service.

- Georgiann S, Sep 2015

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