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Cuba Inside Out

9 days

9 Day People-To-People Journey

Exclusive People-to-People Discoveries with our Insider’s Access

+ Delve into Cuban history from the Colonial-era sugar trade as it developed in the Valley de los Ingenios to the Revolutionary events that unfolded in Santa Clara.
+ Discover the architectural grandeur of Cuba’s most important Colonial-era cities… Old Havana, Trinidad and Cienfuegos.
+ Meeting professional dancers and attending a private choral concert are fun and intimate ways to experience Cuba’s enduring passion for dance and music.
+ All inclusive dining in the island’s finest restaurants; we’ve picked them for their innovative presentations of Cuban cuisine and unique décor - from Colonial elegance to Bohemian chic.
+ With our unhurried overnight stay in the Viñales Valley, you’ll have time to meet with tobacco farmers, learn to handroll a cigar, and explore the region on a carriage tour or horseback ride.
+ Ride in a vintage American convertible to Finca Vigia where Hemingway lived for 20 years.
+ Engage in lively informal conversation with people from all walks of life including a journalist, artists, historian, chef and scholar… It’s a wonderful way to get to know Cuba, inside and out.

Discover 5 UNESCO World Heritage Sites c

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Welcome to Santa Clara, Cuba

On arrival in Santa Clara, you’ll be met and escorted to the Hotel Central Encanto. With only 23 guestrooms, our charming hotel enjoys a privileged location among the Colonial and Neoclassical landmarks that overlook the town’s main square. A guided evening walk with a local historian is the perfect introduction to Santa Clara and its monuments.

Our first night in Cuba begins at Café Museo Revolución. This unique restaurant-cum-museum pays homage to the Cuban revolution with the owner’s collection of photos, old uniforms and other rare memorabilia. If you wish, there will be time to enjoy one of the Café’s famous Mojitos before we move on to dinner at one of our favorite local restaurants.  Meals D


Revolutionary History + Rarely Visited Coastal Communities

The Battle of Santa Clara in December 1958 was a turning point in the Cuban Revolution. This morning you’ll explore these historic events and the man behind them at the Che Guevara Memorial. Here you’ll find a small museum, Guevara’s mausoleum, and an 82-foot statue of the revolutionary. Then explore earlier chapters of history in the quiet, rarely-visited town of Sagua La Grande. Founded as a Spanish settlement, its neo-classical architecture reflects the wealth gained from the sugar industry. Our People-to-People activity with a journalist and Rumba troupe promises insight into the region’s Afro-Cuban heritage.

Set on the north coast, Isabela de Sagua isn’t far from Santa Clara - but life here seems worlds away; it’s a quiet region that’s rarely-visited and it offers a chance to experience a side of Cuba still untouched by the changes sweeping the island. Spend time with fishermen for in intimate look into daily life and learn more about the town’s history as a trading port in the 1800’s. For lunch, you’ll savor the region’s fresh seafood accompanied by the tunes of a lively trio. Back in Santa Clara, we’ll have dinner with community members and exchange stories about life in Cuba and the USA. Tonight, those who wish can check out the nightlife at El Mejunje. Set in an abandoned city building with loads of atmosphere, this popular spot features a variety of live entertainment, from local dance bands to traditional trova singers.  Meals B+L+D


Through the Valley de los Ingenios to Trinidad

Departing Santa Clara after breakfast, we travel southward into the Valley de los Ingenios c. This UNESCO World Heritage Site bears testimony to the development of the island’s sugar cane industry. In the early 19th century, there were 11,000 slaves working here on the plantations and sugar mills. Learn more about this history as our guide shows you the ruins of these mills, the old slave quarters and some of the restored homes of long-ago sugar barons.

Refresh with a glass of Guarapo, a traditional drink extracted from freshly-cut sugarcane. Then continue to Trinidad c for a walking tour. Founded in the 16th century, its architectural landmarks include the Palacio Brunet and the Palacio Cantero, built with wealth from the sugar trade. After lunch with the owner of a charming guesthouse, we’ve arranged a Salsa dance lesson with a local expert. Later, another People-to-People activity finds you engaging with students and staff at a local school.

Then check in to the stylish Iberostar Grand Hotel Trinidad, a pistachio-colored landmark overlooking Plaza Carillo. You’ll have time to explore on your own, perhaps stopping in a café or bar for a refreshing Cuba Libre or Mojito; our guide will be happy to offer suggestions. This evening you’ll dine at La Redaccion. Set in a restored Colonial residence, it offers daily-caught seafood and organic farm-to-table fare. A local journalist will join us for dinner – ensuring lively conversation.

Trinidad is famous for its nightlife and music scene. This evening, those who wish can join our guide at the popular Casa de la Musica, where talented musicians perform a variety of Cuban genres from Son to Salsa.  Meals B+L+D


Onward to Cienfuegos c

Leaving Trinidad this morning, we’ll enjoy a scenic drive to Cienfuegos. Established in 1819 and known as the “Pearl of the South,” this is one of the island’s newest settlements. It’s also a UNESCO World Heritage Site, recognized for its architectural diversity. You’ll discover a fine Colonial district and a collection of early 20th-century villas. We’ll begin our touring at the Cienfuegos Botanical Garden. Established in 1899 by a New Englander named Edward Atkins, the garden began with a collection of rare plants which this wealthy sugar tycoon cultivated on his own estate.

In the heart of town, our walking tour focuses on the historic buildings that overlook Jose Marti Park. We’ll also join residents along the colorful commercial streets and in the markets of town. It’s another chance to experience life in Cuba. At the Palacio del Valle, we’ll discover an architectural gem set at the end of Punta Gorda – a slice of land that extends into the bay. Built in the early 1900’s with colonnaded balconies and turrets, it reflects Spanish, Moorish, Gothic and Baroque styles.

At midday, a boat will take us to a nearby fishing village where we’ll enjoy a seafood lunch. Back in town, we’ll head to the Tomás Terry Theater, easily recognized by the gold-leafed mosaics that adorn its façade. The interior of this 950-seat theater features Carrara marble, hand-carved Cuban hardwoods and ceiling frescoes. As part of our People-to-People program, enjoy an enriching conversation and a private concert with members of the renowned Cienfuegos Choir.

After meeting with members of UNEAC, an organization of Cuban writers and artists, we’ll check in to the Melia San Carlos Hotel. This stylish new hotel is set in a restored 1920’s landmark. After dinner, those who wish can return to UNEAC with our guide for some musical entertainment.  Meals B+L+D


Journey to Havana c

After breakfast, we’ll travel to Havana. With our unique approach, your sightseeing begins on a ferry as we take you across the harbor. Away from the hustle-and-bustle of Old Havana, where most visitors begin their exploration, you’ll have a better introduction to the city’s centuries-old seafront forts and its history as a vital trading port. Stepping ashore in the quieter lesser-visited district of Regla, we’ll delve into the city’s enduring Afro-Caribbean traditions. One example we’ll learn about is Santeria, a local religion that blends elements of Roman Catholicism with Yoruba beliefs that trace their roots to Africa. Then we’ll get another taste of the island’s music scene at a recording studio that has attracted a wide variety of musicians. These include Dave Matthews, Smokey Robinson, and some of the island’s top hip hop artists.

After lunch at Doña Eutimia, we’ll enjoy a walking tour through Old Havana. Immerse in the rhythms of city life and learn about the Baroque and Neoclassical monuments of this UNESCO World Heritage Site. Our tour will take you through the city’s four principle town squares – from the charming Plaza de San Francisco and impressive Plaza de la Catedral to Plaza Vieja and the lively vendor-filled Plaza de Armas near the waterfront. Then we’ll check in to the deluxe Iberostar Parque Central in the heart of Havana for a 3-night stay. You’ll have time to refresh before we head out to enjoy our first night in this energetic city.

This evening we’ll dine at Tierra, one of the city’s newest restaurants. It’s located inside La Fabrica del Arte Cubano, so after dinner you might explore this contemporary cultural center. It’s set inside an old factory and filled with trend-setting galleries and performance spaces. Here you can experience the cutting edge of Cuba’s vibrant cultural scene – from photography and painting to cinema and performance art.  Meals B+L+D


Culture + Art in the Capital

After breakfast, step into your waiting vintage American convertible. Riding in style, we’ll be chauffeured outside of town to Finca Vigia. Built in 1886, Ernest Hemingway purchased this hilltop residence in 1940. He lived here for nearly 20 years and during that time he wrote two of his most famous works – For Whom the Bell Tolls and The Old Man and the Sea. Peering through its large open windows, you’ll see hundreds of the author’s personal belongings almost exactly as he left them when he departed Cuba for the last time in 1960.

Then continue to El Morro, Havana’s harborfront fortress, we’ll have views of the city and the fortress on the other side of the harbor. Close to El Morro, an open-air military museum is home to Soviet weapons, including some of the missiles that factored into the 1962 military standoff between the U.S. and Soviet Union.  Next, we head to Cojimar, the seaside village that inspired The Old Man and the Sea. It was from the Cojimar pier that Hemingway would set out in his 38-foot fishing boat to make liquor runs to Florida.

After lunch, we’ll delve into Havana’s arts scene. Photography, sculpture and painting are among the media we might explore as we spend time with artists in their galleries and studios. We’ll finish the afternoon at the National Museum of Fine Arts, the nation’s foremost collection of international and Cuban art. Hewing to this same theme, we’ve arranged dinner at a local studio-cum-restaurant of one of our favorite Cuban artists, where you have the chance to see contemporary works while dining with their creator. Later, those who wish can end the night at the Tropicana, the legendary cabaret that first opened its doors in 1931.  Meals B+L+D


From Rumba to the Revolution

The roots of Rumba music and dance can be traced to the slave trade that brought these traditions from Africa to the Caribbean. What we in America now consider to be Rumba is most closely associated with several genres that have long been popular in Cuba - including Guaracha and Son. This morning, we’ll delve into this fascinating history with a special People-to-People activity in a family apartment in Old Havana. In the company of a Rumba professional, this lively morning exchange will of course include a dance lesson for those who wish. Next, we’ll head to Callejón de Hamel. Adorned with bright murals and sculptures, this narrow alley in Central Havana has emerged as a thriving community project devoted to Afro-Cuban music and dance.

Around midday, we’ll visit a market, grocery store and ration card facility to learn more about daily life and how food prices are determined. Over lunch at Grados, a traditional Cuban paladar, the owner-chef will share personal stories about his recipes and food – much of it drawn from the home-cooked meals of his childhood.  This afternoon delve into Cuban history before and after the Revolution – from the infamous 1950’s mobsters who spent much time at the elegant Hotel Sevilla to the monuments of Revolution Square. We’ll also visit the Museum of the Revolution, set in the former Presidential Palace.

 We’ll finish the afternoon with an informal question-and-answer session with a scholar from one of Havana’s fine universities. Engaging, deeply knowledgeable and erudite, their insights will illuminate our understanding of Cuba and its evolving role on the world stage.   You’ll have time to refresh at the hotel before we dine tonight at La Guarida. Opened in 1996 by Enrique and Odeisys Nuñez, this pioneering paladar is still a Havana legend. It’s famed for its Bohemian chic décor and innovative preparation of traditional Cuban dishes. If you wish to take advantage of your final night in Havana and experience more of its nightlife and music, our guide will be happy to offer suggestions and assistance.  Meals B+L+D


Into the Viñales Valley c

This morning we’ll travel westward into the beautiful Viñales Valley. The area is recognized as a UNESCO World Heritage Site for its enduring agricultural traditions and the authentic architecture of its farms and villages. Its pastoral fields are encircled by mountains and interspersed with rugged limestone outcrops that soar as high as 900 feet above the surrounding terrain.

The region is also the island’s tobacco heartland and we’ll spend our first few hours delving into the generations-old farming techniques that produce some of the world’s finest cigars. From the plantations and their working livestock to the tobacco drying houses, we’ll learn much about this vital sector of Cuban agriculture. A local farmer will even teach us how to handroll a cigar with techniques that have changed little over the generations.

We’ll also meet an experienced horse trainer and spend time with farmers for a deeper look into their life – including musical traditions that trace their roots to the earliest Spaniards. Later this afternoon, we’ll check in to the inviting Rancho San Vicente, where your air-conditioned casita offers comfortable accommodations surrounded by the region’s wooded landscapes. Your choice of a carriage ride or guided horseback riding adventure is a delightful way to experience the timeless rhythms and landscapes of the Viñales Valley.

This evening’s farewell dinner at a local inn features Lechon Asado, a Cuban favorite. The inn's owner will be on hand along with local musicians and dancers, promising a congenial and unforgettable evening.  Meals B+L+D


Back to Havana for Departure

Check out after breakfast and travel back to Havana. You’ll be taken directly to the airport for your homeward flight.  Meals B

*Each of our people-to-people departures is individually arranged.  Your final itinerary may vary slightly as venues unexpectedly open and close.

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FAQs About Travel to Cuba  

See this document to answer all your questions about travel to Cuba with
Alexander+Roberts.   Click here.

Flights for this Tour to Cuba  

From wherever you might live in North America, we'd be pleased to provide airfare in economy, premium economy or business class. Airfares to Cuba include mandatory Cuban health insurance and Cuban departure tax.  By booking with A+R, we can assist with flight disruptions, delays or cancellations while you travel.

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