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The Leader in Small Groups on the Road Less Traveled
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2017 Cuba: A Bridge Between Cultures

Havana • Cienfuegos • Trinidad

88% Traveler Excellence Rating Read reviews

12 Days from only $4795 including international airfare from Orlando or Tampa

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 Laurent Tixhon and Ben Louis Nicholas
Young Gloves

Get a glimpse of Cuban boys coming of age in makeshift boxing rings on the streets of Havana.

Courtesy BBC.com Travel
My City: Havana

Enjoy a local perspective on Havana—one of Cuba’s most spirited cities.

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.

©2015 The New York Times
A Night in Havana

Learn about a few of Cuba's trendy hot spots from an ex-pat living in Havana.

FROM
$4795
12 DAYS
$400/DAY
including international airfare from Orlando or Tampa
12 DAYS FROM $4795 Small Group Adventure Only
 

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

Find the Adventure That’s Right for You

Our Activity Level rating system ranks adventures on a scale of 1 to 5 to help you determine if a trip is right for you. See the descriptions below for more information about the physical requirements associated with each rating.

Activity Level 1:

1 2 3 4 5

Easy

Travelers should be able to climb 25 stairs consecutively, plus walk at least 1-2 miles over some uneven surfaces without difficulty. Walks typically last at least 1-2 hours at a time. Altitude can range from zero to 5,000 feet.

Activity Level 2:

1 2 3 4 5

Moderately Easy

Travelers should be able to climb 40 stairs consecutively, plus walk at least 2-3 miles over some uneven surfaces without difficulty. Walks typically last for at least 2-3 hours at a time. Altitude can range from zero to 5,000 feet.

Activity Level 3:

1 2 3 4 5

Moderate

Travelers should be able to climb 60 stairs consecutively, plus walk at least 3 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 3 or more hours at a time. Altitude can range from 5,000 to 7,000 feet.

Activity Level 4:

1 2 3 4 5

Moderately Strenuous

Travelers should be able to climb 80 stairs consecutively, plus walk at least 4 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 4 or more hours at a time. Altitude can range from 7,000 to 9,000 feet.

Activity Level 5:

1 2 3 4 5

Strenuous

Travelers should be able to climb 100 or more stairs consecutively, plus walk at least 8 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 4 or more hours at a time. Altitude can range from 10,000 feet or more.

Itinerary Overview

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 visit 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'll have lunch at paladar Galeria Amos 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.

    Lunch is on your own, and then you may return to our hotel or continue exploring at your own leisure. Later this afternoon, 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 begin our drive toward and through the 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, as we'll discover during a visit to a coffee-growing garden where we have an opportunity to taste the local coffee. We'll also pause for lunch nearby. Next, we visit a local farm 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, before continuing toward Cuba's southern coast.

    Upon arrival in Trinidad, 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. We'll check into our hotel late this afternoon, before dinner at a paladar called El Galeón near Trinidad's port.

  • We start this morning with a visit from 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 transfer into colonial Trinidad for a walking tour of the historic core—a UNESCO World Heritage Site. We'll begin in the home of a local family, then 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. Then, lunch is on your own.

    This afternoon, we'll meet with artisans at the arts and crafts market. Then, you may choose to return to our hotel, or continue exploring Trinidad at your own leisure.

    Dinner this evening is at Paladar San Jose in Trinidad. After our meal, we can speak with the owners about the difficulties in starting a private business in Cuba.

  • 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 a local paladar, Ajiaco Café, perhaps you can ask 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 lunch, we'll visit El Cristo de Habana, a large statue of Jesus Christ with sweeping views over the city of Havana. Next, we gain further insights into Cuban history and culture at the ornately historic Colón Cemetery, a sprawling 19th-century burial ground with elaborate memorials to figures from Cuba’s past. We arrive at the Hotel Nacional late this afternoon and regroup later for dinner at Paladar El Figaro. We will have a discussion with the staff on Arte Corte, a community project, and discover how this restaurant is part of that project.

  • After breakfast this morning, we venture to the eco-village of Las Terrazas. Our first stop is the local school (when in session), and then we'll visit the studio of a local artist. We'll learn more about this village, a UNESCO Biosphere Reserve, at its community center, where a local guide will share a coffee with us and describe village life. A local bodega, a visit with a local doctor (when available), and lunch at a nearby restaurant round out our time in this fascinating place.

    This afternoon, 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. Dinner is on your own this evening.

  • 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.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 handcraft market, where we'll meet Cuban artisans and learn about their lives.

    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. We'll learn about the time and hard work that young entrepreneurs devoted to transforming this house into the popular restaurant it is today.

    • 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

Read Travel Planning Guide

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