Cuba Inside Out (2025 Itinerary)

On arrival in Havana, you’ll be met and escorted to your hotel, perfctly located in Old Havana. Tonight enjoy dinner with your fellow travelers at one of our favorite Havana restaurants. Meals D

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. Meals B+L+D

This morning visit one of Havana's oldest cigar factories and try your hand at rolling a cigar. Then travel outside Havana, where the cityscape gives way to the beautiful landscapes of Cuba's countryside. Here, you'll visit Finca Tungasuk, a 32-acre family farm, and meet its owners: Alfredo, a self-proclaimed Foodie from Peru who used to be a UN election monitor, and Annabelle, a Nicaraguan chef trained at the illustrious Ferrandi Culinary Institute. You'll experience the tranquility of rural Cuba, while exploring its rich agricultural heritage, learning the basics of planting, harvesting and managing a sustainable farm operation.  Then enjoy a delicious farm-to-table lunch.  After our return to Havana, we have time to relax before heading to La Guarida for dinner. 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. After your meal, unwind with a premium rum and cigar pairing, where rich flavors and smoky notes come together for a refined, relaxing finish. Meals B+L+D

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. 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. 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. 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. Then, 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. Then stop at the Colon Cemetery, world renowned for its historical and elaborately sculpted memorials. 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. We head to Trinidad where we check into our hotel. Tonight, dine at a charming venue that is part restaurant, part gallery showcasing work by local ceramic artist, Yami Martinez.  Meals B+L+D

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. Then we head northeast for an afternoon lunch and visit to a farm in Topes de Collantes, a beautiful nature reserve outside Trinidad, offering fantastic views of the city, the valley and the sea.  It is well-known for its pristine nature, clean air and curative properties.  The farm cultivates honey from bees that nest in the earth and grows its own coffee, so we enjoy a lunch of truly local flavors which learning of Cuban country life with a background of vintage LPs playing on the owner’s old gramophone. Tonight, enjoy dinner at a lovely 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

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 your hotel. 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

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.