Eastern Cuba: Crossroads of History and Culture

  • 11-day journey including Havana, Santiago de Cuba, and Baracoa
  • Get immersed in the distinctive culture of eastern Cuba

Expedition Details


Soak up the captivating culture of eastern Cuba on a journey that focuses on people and culture. Experience the irrepressible spirit of Havana on city walks and encounters with its residents. Then head east to Santiago de Cuba and delve into a vivid history from colonial times to the Cuban Revolution. Visit the gravesite of José Martí and the battlegrounds where Teddy Roosevelt’s Rough Riders fought. Explore Baracoa, the island’s oldest Spanish settlement, and meet descendants of the indigenous Taino people. Along the way, get to know folk dancers and musicians, artists, farmers, and fishermen.

Trip Highlights

  • Meet with members of the National Union of Writers and Artists of Cuba, an organization that has helped Cuban culture flourish since the revolution.
  • Trace the history of the Rough Riders and the Buffalo Soldiers at San Juan Hill and join historians for walking tours of Santiago de Cuba and Baracoa.
  • Explore the unique cultural heritage of eastern Cuba during a visit to an artists’ colony and an afternoon with a troupe of Afro-Cuban dancers and musicians.
  • Pay a visit to a village where descendants of the indigenous Taino people maintain their traditional lifestyle and enjoy a demonstration of local dance, music, and cuisine.

Itinerary - 11 Days

Day 1 — Miami/Havana, Cuba

Depart Miami on a charter flight to Havana. Upon arrival, get oriented on a city tour and stop for lunch before checking into our hotel. Gather for a welcome reception and dinner tonight.
Hotel Parque Central or Melia Cohiba (L,D)

Day 2 — Havana

Venture into neighborhoods beyond Old Havana with a representative from the city historian’s office to see current restoration projects and learn of the city’s successes and challenges. Then meet a prominent Havana artist to discuss the state of the arts in Cuba. Pay a visit to the University of Havana and join professors and students for a panel discussion about the Cuban education system.
Hotel Parque Central or Melia Cohiba (B,L,D)

Day 3 — Havana

In 1961, Cuba’s intellectuals and artists formed the National Union of Writers and Artists of Cuba to protect and celebrate Cuban culture. With more than 9,000 members today representing myriad art forms from poetry to sculpture, the union remains a major player in the country’s thriving cultural scene. Meet with journalists and artists at the union’s offices to discuss the intersection of arts and the revolution and current events on the island. Visit an organic farm and speak with farmers about the country’s emerging agricultural sector, and stop by an environmental organization for a glimpse of local conservation efforts.
Hotel Parque Central or Melia Cohiba (B,L)

Day 4 — Havana/Santiago de Cuba

Fly to Santiago de Cuba, set on the southeastern shores of the island. Established by Spanish conquistadores in the early 16th century, Santiago de Cuba served as the capital of colonial Cuba, a battleground during the Spanish-American War, and the birthplace of the Cuban Revolution. After lunch, stop by the 17th-century citadel San Pedro de la Roca, a UNESCO World Heritage site perched at the water's edge. This afternoon, visit a performing arts community project that provides an artistic outlet for neighborhood children.
Hotel Melia Santiago (B,L,D)

Day 5 — Santiago de Cuba

Join a cultural studies expert this morning for a discussion of the region's Afro-Cuban religion and culture. Then head to the Moncada Barracks, where in 1953, Fidel Castro and a small group of rebels launched the Cuban Revolution with a daring attack on the military. Trace the movements of Teddy Roosevelt’s Rough Riders and the Buffalo Soldiers at San Juan Hill, site of one of the most important battles of the Spanish-American War. Then step back in time with a city historian on a walking tour of the historic district and learn about the city’s dramatic past. Later, meet with prominent artists to discuss their roles in the revolution.
Hotel Melia Santiago (B,L,D)

Day 6 — Santiago de Cuba

This morning, travel into the countryside to an artists’ colony. Enjoy time to visit the studios of sculptors and painters and speak to the artists informally about their lives and work. After lunch, return to Santiago and head to the Teatro Heredia to view a rehearsal session of the Ballet de Folklorico Oriente, one of the first troupes to showcase Afro-Cuban dance. Afterwards, take the opportunity to meet the dancers, musicians, and directors and learn more about the group and the history of this dance form.
Hotel Melia Santiago (B,L)

Day 7 — Santiago de Cuba/Baracoa

Begin the day with a visit to the Cementerio Santa Ifigenia, one of Latin America’s most important and grandiose cemeteries. Wander past elaborate marble tombs with a local expert and see the final resting places of Cuban national hero, José Martí, and the first president, Tomás Estrada Palma. Later, travel to Baracoa, inaccessible by road until 1965. After settling into our hotel, enjoy dinner in town.
Hotel Castillo or Porto Santo (B,L,D)

Day 8 — Baracoa

Set on a remote bay on Cuba’s northeastern coast, Baracoa was the first Spanish settlement on the island and retains the feel of a colonial village. At Fuerte Matachin, one of the three original forts built to protect the city, meet the city historian and set off on a walking tour of Baracoa’s old city. Then drive into the countryside to a rural community where many residents are descendants of the indigenous Taino people. Get to know this Carib culture and witness its traditional music and dance. Back in Baracoa, learn about a children’s community project through a panel of the project’s instructors.
Hotel Castillo or Porto Santo (B,L)

Day 9 — Baracoa

Today, meet with farmers on an excursion to a cacao plantation. Follow the process of turning the beans into chocolate, and learn about the crop’s importance to the local economy. Sit down to lunch on the banks of the Toa River before returning to Santiago this afternoon.
Hotel Melia Santiago (B,L,D)

Day 10 — Santiago de Cuba

Head to the historic district this morning for a visit to the Church of the Holy Trinity and enjoy an opportunity to interact with its members. Spend the afternoon on a small island in Santiago Bay, where the local fishing community incurred significant damage during Hurricane Sandy. Explore the island, engaging with its residents, learning about its fishing industry, and witnessing the post-Sandy rebuilding efforts. Tonight, toast our adventures in eastern Cuba at a farewell reception and dinner.
Hotel Melia Santiago (B,L,D)

Day 11 — Santiago de Cuba/Miami

After breakfast, transfer to the airport for your return flight to Miami.

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This expedition is not currently being offered.

Activity Level

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What To Expect

Please Note: This trip is permitted by a special People-to-People license from the Department of the Treasury’s Office of Foreign Assets Control. This itinerary was designed to provide an immersive experience with numerous opportunities for meaningful interaction with Cubans. Travel restrictions in Cuba, such as limits on how much one may spend and what may be purchased, will be provided in your pre-departure materials.

While we do our best to adhere to the itinerary listed here, traveling in Cuba requires flexibility, and changes to hotels and activities may occur.