Highlights

2026 Departure Dates:

February 23
March 9, 16
April 20
September 28
October 19, 26
November 2

These are small group, guaranteed departures.  Perfect for groups of less than 15 people.

Itinerary

DAY 1: DEPART USA – ARRIVE HAVANA

Upon arrival in Havana at the Jose Marti International Airport and clearing customs, meet your local English speaking Cuban Tour Guide outside the baggage terminal. Your drive from the airport orients you with Cuba’s enigmatic capital city, whose nearly 500-year Old Havana is home to the largest collections of Spanish-Colonial architecture in the Americas. Make a photo stop and learn more about the Plaza de la Revolucion, the center of Cuban political life where millions of Cubans listened to speeches of Fidel Castro. Check into your hotel and unpack for your five night stay. Dinner is included this evening.

(D) Overnight: Havana

DAY 2: OLD HAVANA (UNESCO) – MUSEUM OF THE REVOLUTION – JOSE FUSTER

This morning enjoy a guided walking tour of pedestrian only Old Havana, a UNESCO World Heritage Site. See the beautiful Cathedral de la Havana, built in baroque style in 1748 and learn about its preservation and continuous restoration. Next, enjoy a fascinating tour of the Havana Club Rum Museum with a local Cuban rum expert to learn about the history and process of making Cuban Rum and an opportunity to sample the differences. Following lunch at a local Paladar in Old Havana this afternoon we visit the famous Museum of the Revolution that displays documents and artifacts, weapons and planes from the revolution. Learn about the Bay of Pigs, the 1961 historic clash between the CIA trained Cuban exiles & rebel forces. Next head to the charming fishing village of Jaimanitas to visit the incredible Home and Work Shop of world famous artist, painter and ceramicist Jose Fuster, often called the “Picasso of Cuba”. He has adorned an entire neighborhood with colorful ornate mosaics. Here we spend time with to discuss the influence of the artist’s work and their lives and community. Dinner is on your own this evening allowing you to explore the fine restaurants, cuisine and Jazz clubs of Havana. Perhaps even take in the world famous Tropicana Cabaret Show on your own that offers an evening of music and history at this famous nightclub show that presents song-and-dance performances of 1950’s Cuba. (B,L) Overnight: Havana

DAY 3: CIGAR FACTORY – HABANA COMPAS

This morning following breakfast we begin the day with a fascinating visit and guided tour with a local cigar expert to the La Corona Cigar Factory. See firsthand and learn about the history and the process of Cuban cigars being hand rolled. The factory rolls such brands as Hoya de Monterrey and Cuaba & Punch. Next enjoy a performance by the amazing Habana Compas Dance Group. Interact with the students and teachers to learn more about the Cuban dance culture. Next, tour the famous Nacional Hotel, once Havana’s flagship hotel that has hosted celebrities and world leaders during its heyday, such as Winston Churchill and Frank Sinatra to name a few. Free time to explore this historic property housing pictures and nostalgia from a by gone era or enjoy a Mojito. Meet a former professional Cuban baseball player and join in a discussion regarding the history and love of this game in Cuba. Religion has always played an important role in Cuban society. Enjoy a fascinating walking tour of the Colon Cemetery founded in 1876, and noted for its elaborate sculpted memorials containing more than 500 major mausoleums and chapels. The cemetery is the final resting place for famous Cubans including artists, writers, musicians and ballplayers. Dinner is included this evening at a local Paladar.

(B,L,D) Overnight: Havana

DAY 4: VINALES VALLEY (UNESCO) – PINAR DEL RIO

Today we travel out of Havana and into the rural Cuban countryside to the Vinales Valley located in the western most mountainous range in Cuba and declared a UNESCO World Heritage Site. This region, the western province of Pinar del Rio is known for its stunning scenery, a landscape of prehistoric looking flat-top mountains or “mogotes”, tobacco plantations, caves and rivers. Next, visit a traditional Tobacco Farm and Farmhouse to meet with the farmer to learn about tobacco cultivation, the drying process and experience a cigar rolling demonstration inside the drying hut. Enjoy a visit inside his farmhouse, meeting and interacting with his family and maybe even enjoy some Cuban coffee. An incredible opportunity to witness up close, how Cuban families live in a rural setting. Next enjoy lunch at the beautiful Finca Paraiso Paladar (organic farm) offering incredible panoramic views of the Vinales Valley and an opportunity to meet the Cuban family that owns this organic farm. Later stop at the Los Jasmines viewpoint offering panoramic views of the Vinales Valley and an opportunity to enjoy the spectacular scenery and take photos of this beautiful and unique region of Cuba. Return to Havana later this afternoon with the evening on your own to explore Havana’s many outstanding Paladars, Jazz clubs or simply relax.

(B,L) Overnight: Havana

DAY 5: HEMINGWAY FARM – CLASSIC CAR CLUB

Next enter the world of Ernest Hemingway with a visit to Hemingway’s Farm, Finca La Vigia (meaning ‘lookout house’). This beautiful property hosts the house where the Nobel Prize winner lived with his wife Martha for 21 years. View the perfectly preserved home where many of the Hemingway personal furniture and belongings remain intact. View his famous boat on display, the Pilar in which he used to patrol for Nazis in the Caribbean waters and featured in his novel “Islands in the Stream”. A photo stop is made at the Morro Castle, built in 1589, to protect the mouth of the Havana Harbor. “Morro” in Spanish means a rock which is very visible from the sea and therefore serves as a navigational landmark. Perched on the headland on the opposite side of the harbor from Old Havana it can be viewed from miles around as it dominates the port entrance. Next visit the San Jose Craft Market and Art Center to meet and interact with the local artists to discuss and learn of the importance of their art in Cuban culture. Learn from the artists who share their experiences of pursuing the arts with limited access to materials and funding. Before dinner, meet the local Cuban Old Style Car Club owners. A chance to interact and talk with the owners and learn why Havana’s streets are filled with vintage American automobiles and understand what it takes to keep them on the road. Enjoy a drive through the streets of Havana in a vintage car to your farewell dinner at a one of Havana’s top Paladars. After dinner you have an opportunity to meet and discuss with the owners how this private Paladar enterprise works in Cuba.

(B,L,D) Overnight: Havana

DAY 6: HAVANA – FLIGHT BACK TO USA

Breakfast is included this morning. Today we say goodbye to Cuba and the new friends made. Transfer to the airport for your return flight home with incredible memories of the amazing people and culture experienced on your Cuba Discovery tour. (B)

Itinerary is subject to change. It’s very common for the daily activities and people to people interactions & visits to be interchanged and experienced on different days than this printed itinerary. All visits and experiences will be included as written in this itinerary, but could be on different days due to availability and schedules.

Tour Map