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Cuba Inside Out

9 days

Never more than 16 guests + Guaranteed Departures

Our Distinctive A+R Style

  • Delight in the colonial architecture of Havana, Trinidad and Cienfuegos, Cuba’s most important cities. 
  • Ride a vintage American convertible to Finca Vigia where Hemingway lived and wrote over 20 years. 
  • Engage with Cuban artists and attend performances by dancers and singers, even a private choral concert. 
  • Authentic dining in a variety of settings, including some of the island’s finest restaurants. 
  • Explore Cuban history from the earliest days of the sugar trade to the Revolution in Santa Clara. 
  • Travel confidently in full compliance with all government requirements for Support of the Cuban people.

Show all itinerary details

Day
1

Welcome to Havana, Cuba

Voya Boutique Hotel - Havana, Cuba

On arrival in Havana, you’ll be met and escorted to the charming Cuban Art Hotel. Tonight enjoy dinner with your fellow travelers at one of our favorite Havana restaurants.  Meals D

Day
2

Culture and Art in the Capital

Voya Boutique Hotel - Havana, Cuba

After breakfast, 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. Then we’ll get another taste of the island’s music scene at a recording studio that has attracted a wide variety of musicians, including  Dave Matthews, Smokey Robinson, and some of the island’s top hip-hop artists. We’ll also learn about Santeria, a Cuban cult that blends elements of Roman Catholicism with African religious traditions.  Next enjoy a walking tour through Old Havana and immerse in its urban rhythms while we explore the Baroque and Neoclassical elements of this UNESCO World Heritage Site. 

After lunch, we’ll delve into Havana’s art and music scene. Photography, sculpture and painting are among the media we’ll encounter as we spend time with artists in their galleries and studios. Later, in the company of a Rumba professional, we’ll experience this art form of music and dance as well as a chance to try it out. We’ll continue on to Callejón de Hamel in Central Havana that has emerged as a thriving community project devoted to Afro-Cuban music, dance and art. Tonight, we’ll dine 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.  Meals B+L+D

Day
3

Cigars and the Vinales Valley

Voya Boutique Hotel - Havana, Cuba

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 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 Spaniard colonists.  We return to Havana for dinner and meet the owner chef, Ivan Justo, whose private restaurant is in a building that is 200 years old!  Meals B+L+D

Day
4

From the Revolution to Hemingway

Voya Boutique Hotel - Havana, Cuba

After breakfast, 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. Around midday, we’ll visit a produce market and grocery store with a chef to learn more about daily life and how food prices are determined. Over lunch at Jibaro, we’ll learn to make mojitos and dine on typical Cuban food, surrounded by salvaged pieces of architecture from Old Havana. Following lunch, 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 harbor fortress for 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. Dinner tonight at Otra Manera is set in a converted 1950s mansion with a sleek style that complements the excellent cuisine of this new, private restaurant. For those who wish a late night, your guide can assist with tickets to the Tropicana, the legendary cabaret that first opened its doors in 1931. Meals B+L+D

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.   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 engage in conversation with members of the renowned Cienfuegos Choir who will provide a private concert. After check in at Casa Buenavista, our conversations continue as we meet with members of UNEAC, an organization of Cuban writers and artists before enjoying dinner at Camilla’s, one of our local favorites.  Meals B+L+D

Day
6

Enroute to Trinidad, we begin touring the Cienfuegos Botanical Garden. Established in 1901 by a New Englander named Edward Atkins, the garden began with a collection of rare plants from all over the world which this wealthy sugar tycoon cultivated on his own estate. We’ll arrive in Trinidad for lunch at Oscar y Patricia’s Paladar where the owner is also a musician. After checking in at Hotel JM432 in the heart of town, we explore the cobble-stoned streets of this UNESCO World Heritage Site on 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. Tonight, enjoy dinner at La Redaccion, a charming seafood restaurant set in a colonial house from the 1800s. Since Trinidad is famous for its nightlife and music scene, we 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

This morning we visit a local school and then head to the Salsa Club. No visit to Cuba is complete without trying the steps of this lively dance. After lunch, we travel into the Valley de los Ingenios, another UNESCO World Heritage Site that 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 in the 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.  Meals B+L+D

Day
8

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. Before exploring other sites, refresh with a glass of Guarapo, a traditional drink extracted from freshly-cut sugarcane. We visit the parks and monuments of Santa Clara before arriving at the 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. A popular lunch spot, the café has great sandwiches, coffee and milkshakes. We head back to Havana, and check into the Voya Boutique Hotel once again. Our farewell dinner tonight is at Jama, a welcome newcomer to the Cuban restaurant scene, with dishes that are a contemporary blend of Cuban and Japanese cuisine.  Meals B+L+D

Day
9

Bid Farewell to Cuba

Your driver will transfer you to the airport for your flight home.  Meals B

Please note that current US policies governing travel to Cuba require your full participation in all sightseeing and activities as described in our itinerary.

Escorted Cuban Tours MapSearch

Save $1,000 per couple I $500 solo to Cuba throughout 2023

A journey to nearby Cuba is so exciting and memorable that we’re offering a $500 per person incentive throughout 2023 to make it even more appealing.

For travel through March 2023, we’ll deduct $500 per person at time of booking.  For travel April through December 2023, our pay in full offer of $500 off the price at time of booking will apply.
 

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Travel is one of  life's most rewarding experiences, perhaps even more so when it's shared with those you love! Take advantage of our Family & Friends offer and Save $100 per person anytime you book 4 or more people on the same A+R program.

Cuba Special Savings

For travel through March 2023, we’ll deduct $500 per person at time of booking. For travel April through December 2023, our pay in full offer of $500 off the price at time of booking will apply.