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The Leader in Small Groups on the Road Less Traveled
Never more than 10-16 travelers—guaranteed!

2017 Cuba: A Bridge Between Cultures

88% Traveler Excellence Rating Read reviews

12 Days from only $4595 including international airfare from Miami

Havana • Cienfuegos • Trinidad

Courtesy Diego Vivanco
Havana Bikes

In Havana, more than just the cars are vintage. Learn how locals rely on (and strive to maintain) their 1950s bicycles.

Courtesy of David Conover & Paul Villanova
Travelogue: Havana, Cuba 1931

See what life in Havana was like before the Batista regime in this 16mm film footage from 1931

Courtesy Paul Wegschaider
Cuba - Lost in Time

Let the rhythms of Cuba captivate you in this music-driven video, highlighting everyday scenes from across the island.

Courtesy of David Conover and Compass Light Productions
Malpaso: A Cuban Dance Project

Meet the members of a Cuban dance company.

Courtesy of Peter Wisdom and Ian Cross
Planet Food: Cuba

Explore Cuba like a local, finding traces of European and African influences at every corner.

including international airfare from Miami
12 DAYS FROM $4595 Land Adventure Only

Cuba at the Crossroads
See how the culture is adapting to transition. Discover more


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Beat the Crowds to Cuba
Visit this country on the brink of extraordinary change in 2017

Itinerary Overview

Small groups: never more than 12-20 participants

Uncover the mystique of Cuba with Grand Circle Foundation on a journey that reveals Cuba’s complex history, natural beauty, and cultural riches in the most authentic way possible—through its people. Interact and engage with a variety of artists and writers, fishermen and farmers, and Cubans from all walks of life as you stroll the colonial streets of Old Havana, experience Afro-Cuban rumba rhythms of Cienfuegos, and discover the colonial gem of Trinidad. Toss aside any preconceived notions you may have of Cuba—and prepare to be enthralled by the welcoming spirit of the Cuban people and the unforgettable experiences that await you.

Please note: This is a representative itinerary. Features are subject to change as availability is controlled by the Cuban government. While this is the itinerary that we strive to follow, due to local circumstances (such as moveable holidays, museum/site closing days, and weather conditions), it is important for you to understand that we may not always be able to follow this plan in the exact order. The sequence of places visited may vary.

Day-to-Day Itinerary

Havana Trinidad Expand All
    • Accommodations:

    After arriving in Miami today and transferring to your hotel, meet with members of your group for a Welcome Briefing and what to expect for your flight to Havana tomorrow (Please note: No meals are included while you are in Miami).

  • Cuba - Lost in Time

    Let the rhythms of Cuba captivate you in this music-driven video, highlighting everyday scenes from across the island.

    This morning we fly to Cuba. After we exit Cuban Immigration and Customs at the airport, we’ll be met by our Cuban Trip Leader, who will accompany us to lunch at Il Divino, one of Cuba’s new wave of privately owned restaurants called paladares. After our meal, we’ll stop at the nearby sustainable family farm and botanical garden which supplies fresh produce to Il Divino. Then, we’ll make a brief stop at Havana’s historic Plaza de la Revolución.

    Next, we'll continue on to our home for the next few nights, Hotel Nacional de Cuba, an historic hotel overlooking the harbor with views of the sea wall and El Morro Fortress.  Our hotel is located in the Vedado section of Havana, across the street from the Malecón, and close to the University of Havana, the U.S. Embassy, and Coppelia ice cream—featured in one of the most widely viewed Cuban films, Strawberry and Chocolate. An orientation walk around the immediate vicinity will show us this modern part of the city. We'll have dinner together this evening at a paladar called La Moraleja in Havana's Vedado district, where we'll have the opportunity to learn about the difficulties and successes these young entrepreneurs have faced with their private restaurant.

  • Our first full day in Havana begins with a discussion on urban development in Havana, led by Pedro Vazquez, an architect, urban planner, and an associate and advisor to CIERIC, a Cuban NGO focused on habitat, art-related, community-based and socio-cultural issues. Then, we visit a residential neighborhood, where we stop in at a senior center. Sharing photos and stories with senior Habanero residents will give us an intimate glimpse of Cuban family life in this fast-changing island nation. Then we visit a handcrafts market and talk with local artisans before having lunch at a paladar near Habana Vieja. Afterward, we embark on a neighborhood walking tour, where we'll stop and chat with the Cuban people as we walk through the streets and squares of Old Havana. We will see the historic restorations that have revived much of the district’s former splendor—and we begin to gain an understanding of why Havana’s historic heart has earned recognition by UNESCO as a World Heritage Site. Later this evening, we’ll head to a Havana barrio to visit Muraleando, a community arts project of colorful murals and various forms of street art, where we’ll meet with some local artists and view their works. Several of the talented artists will then join us for dinner, which they host in their community.

  • Our morning starts off with an enlightening discussion on U.S./Cuban relations led by a pair of Havana residents, who will give us the “Cuban perspective” on this potentially exciting new era of relations between the two countries. Then we see what life is like for everyday Habaneros when we hop aboard local transportation—bici-taxis—and head to a local market to meet with vendors and mingle with some shoppers. Next, we have an opportunity to interact with children at a day-care facility sponsored by a local church. Then, we visit Plaza Vieja, where you may stroll among the arched colonnades and choose your own lunch from among the many cafes.

    After lunch, our focus turns to the Cuban arts, as we visit the Museo de Bella Artes (Fine Arts Museum). Next, we'll drive to the outskirts of Havana to visit a public art project in Jaimanitas, a village where Cuban artist and sculptor Jose Fuster has decorated more than 80 neighborhood houses with ornate, Gaudi-inspired murals and domes. After touring what has become known as “Fusterlandia in Jaimanitas,” we have an opportunity to ask the artist questions about his living canvas and discuss contemporary Cuban art during dinner with Jose Fuster (or with his son Alex).

  • Today we drive west from Havana to the southern coastal city of Cienfuegos. Home to one of the most captivating natural bays in the Caribbean Sea, Cienfuegos was founded in 1819 by settlers from the former French colonies of Haiti and Louisiana—and has maintained many of its French cultural and architectural influences. Upon arrival, we enjoy a light lunch at our hotel, followed by an introductory stroll through the lively port town, whose historic center is a UNESCO World Heritage Site. This evening, we enjoy a performance of classic Cuban songs by the Cantores de Cienfuegos. Afterwards, we'll get to chat with the talented young singers of this renowned choral group and perhaps share a song of our own with them. Then, we'll have dinner at Villa Lagarto, one of Cuba's privately owned restaurants called paladares. Villa Lagarto is situated at the tip of Punta Gorda with views of the sea.

  • This morning we meet with a few of the writers, artists, and musicians of the Union of Writers and Artists in Cuba (UNEAC) to discuss the role of the arts in Cuban society and how they can help to preserve Cuban culture. Then we visit some artists' studios in Cienfuegos to view their works and hear about the challenges they face in earning a living through their craft. This afternoon, we participate in a social program with some of the younger residents of Cienfuegos. Dinner tonight is at another paladar in Ciefuegos, La Finca del Mar. Then, after dinner, we return to UNEAC to hear a local son band such as Los Naranjos (who have been playing Cuban classics since 1926) perform for us. Son is the lively Afro-Cuban musical style played over a rumba beat that has enjoyed worldwide popularity—and we may find it difficult not to break out in dancing with some of the local artists and writers who will attend the performance with us.

  • This morning we leave Cienfuegos for Trinidad. Along the way, we stop for a visit to Cuba’s largest Botanical Park. Dating back to 1899, the gardens feature collections of palms, orchids, bamboo, and myriad other lovely Caribbean flora spread over almost 250 acres. After leaving the Botanical Gardens, we’ll visit the small town across from them, Soledad, and learn about life in a small rural community. Upon our arrival in Trinidad, we'll have a light lunch at our hotel before we meet with some basket makers at a government sponsored workshop. This will be an excellent opportunity to see the contrast with the free enterprise sites and private entrepreneurs we'll visit during our program. Next, we visit a ceramics studio that has been run by the Santander family for a century. We can take a spin at the pottery wheel as we learn about the secrets of working with clay that have been passed down through several generations of the same family. This evening we discover Cuba's relaxed restrictions on private enterprise during dinner at Trinidad Jazz Café, another of the many small family-run restaurants known as paladares that feature authentic home cooking in an intimate setting.

  • Today is spent in colonial Trinidad. Frozen in time since the sugar boom collapsed in the middle of the 19th century, the cobblestone streets, elegant plazas, and pastel-colored former manor homes of the wealthy sugar barons have changed little since Trinidad's golden age. We start the day bey visiting someone who practices the Santeria religion. During our discussion, we’ll have an opportunity to learn about Santeria, and discover how this religion is widely practiced in Cuba. Next, we'll embark on a walking tour of Trinidad's historic core—a UNESCO World Heritage Site—where we’ll visit a bodega, a local artist, and the church. This gives us a revealing glimpse into everyday life in contemporary Trinidad as we meet some of the people who live in this historic Cuban city, and have discussions with them about their lives, hopes, and dreams.

    We'll have lunch on our own, followed by a visit to the arts and crafts market. Dinner this evening is at Sol Ananda, a beautifully furnished paladar in a former colonial mansion. After our meal, we can speak with the owners about the difficulties in starting a private business in Cuba.

  • After breakfast, we drive out to the surrounding Sierra del Escambray mountain range, an unspoiled wooded landscape of deep valleys punctuated with streams, caves, and exotic flora and fauna. Coffee is also cultivated in the shade of pine and eucalyptus trees of the mountain slopes here, and we visit a small plantation to meet with a coffee farmer and his family to learn what it's like to live and work in this region of great natural beauty. After lunch, we return to Trinidad. Dinner is at our hotel this evening.

  • On our way back to Havana this morning, we stop at Cojímar, the fishing village where Hemingway visited in the 1950s to play dominoes, drink rum, and listen to the stories of the Cuban fishermen who soon became his friends. During our lunch with some of the local fishermen at Bodega Las Brisas, a local paladar, perhaps you can ask them about Gregorio Fuentes, the Cojímar fisherman who was the inspiration for The Old Man and the Sea. Fuentes, who was a close friend of Hemingway's, died in 2002 at the age of 104. After our revealing lunch, we visit Hemingway's home for 20 years in the Havana suburb of San Francisco de Paula. Respected by Cubans for living in a modest area among the people he fished with, Finca La Vigia (meaning “lookout house”) is where the famous author wrote For Whom the Bell Tolls and The Old Man and the Sea. Later this afternoon, we return to the Hotel Nacional de Cuba.

  • After breakfast, a Director of the Ludwig Foundation—a non-profit organization created to promote Cuban culture—will speak with us about the role of dance in contemporary Cuba. Next, we gain further insights into Cuban customs at the ornately historic Colón Cemetery, a sprawling 19th-century burial ground with elaborate memorials to figures from Cuba's past. Then, Malpaso, one of Cuba's first private dance companies, will welcome us into their studio to watch a private rehearsal, followed by a chance to chat with the dance members. After our visit with the Malpaso dance company, we continue on to Havana's historic La Cabaña, an 18th-century fortress complex near the entrance to the Bay of Havana.

    We have lunch on our own and some time to explore the colonial streets of Havana at leisure. Our last evening in Cuba features dinner at Starbien, a renovated colonial mansion tucked into the residential neighborhood of Vedado. Starbien is another of Cuba's privately-owned restaurants called paladares, and we'll have a chance to talk to the entrepreneurs about the recent changes in Cuba.

    • Meals included:

    Today, we bid Cuba a fond adios as we board our flight to the United States.

    Please note: This is a representative itinerary. Features are subject to change as availability is controlled by the Cuban government. While this is the itinerary that we strive to follow, due to local circumstances (such as moveable holidays, museum/site closing days, and weather conditions), it is important for you to understand that we may not always be able to follow this plan in the exact order. The sequence of places visited may vary.

Click below to read our Travel Planning Guide on Cuba: A Bridge Between Cultures

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