*This cruise is no longer available.

Starting at: $8,295 Ask Us A Question or Call 855-330-1542
 Historic building with vintage automobiles, Havana  The sailing ship Le Ponant  Plaza in Cienfuegos  Musician in Havana  Cathedral at night, Havana  Street in Old Havana  Plaza Vieja, Havana

Cuba by Land and Sea

A Full Island Discovery Aboard the 64-guest Le Ponant

11 days from $8,295

*This cruise is no longer available.

or Call 855-330-1542


Take a deep look into Cuba’s culture and geography through our new cruise exploration from Santiago de Cuba in the east to Havana and Pinar del Rio in the west. Begin your program in Miami with a special panel discussion, then enjoy the amenities of a deluxe small sailing ship for six nights and end at a charming hotel in Havana’s Miramar district.

Highlights Include

  • Santiago de Cuba: During three days in this vibrant city, explore the history of the island’s religious and Afro-Cuban traditions as well as the Spanish-American War and Cuban Revolution. Visit the World Heritage site of Castillo San Pedro de la Roca and see the 15th-century Casa de Diego Velázquez, the oldest house in Cuba.
  • Trinidad: Enjoy activities featuring the arts and history of this colonial town, a World Heritage site. Explore a museum showcasing the history of Trinidad and watch rumba and salsa performances at an outdoor music center.
  • Cienfuegos: Learn more about Ernesto “Che” Guevara in nearby Santa Clara, the gateway to Cuba’s historically and agriculturally rich central region.
  • Havana: Meet with people engaged in urban cultural themes, visit Ernest Hemingway’s former home Finca Vigia, and take a guided tour of Old Havana to learn about the preservation of its art and architecture.
  • Pinar del Rio: Spend a day in the Vinales Valley, a World Heritage site known for Cuba’s agricultural efforts and western landscapes. Visit an organic farm and enjoy a home-style lunch with the farmer and his family. 

To see itinerary, please click on an option below.


Day 1 — Home City to Miami

Depart your home city and arrive in Miami, Florida. Transfer to the Double Tree Miami Airport Hotel for one night. During the evening enjoy a briefing on Cuba with your Smithsonian Journeys Expert and local Cuban experts of Miami who will provide a unique perspective on the journey you are about to take.

Day 2 — U.S./Santiago de Cuba, Cuba

Depart the U.S. on your flight to Cuba. Upon arrival in Santiago de Cuba, meet your experienced, English-speaking Cuban hosts and guides, who will accompany you on people-to-people exchanges and be part of your immersion into their way of life. Cuba’s second largest city is perhaps the island’s most vibrant and culturally rich, with its lively music and attractive colonial architecture. Visit the World Heritage site of Castillo San Pedro de la Roca (El Morro), a 17th-century fortress built to protect the important port of Santiago de Cuba Bay. This afternoon, embark Le Ponant and attend the captain’s welcome reception this evening. (L,R,D)

Day 3 — Santiago de Cuba

On the walking tour, see Céspedes Park including historic City Hall, where Fidel Castro announced the victory of the Cuban Revolution in 1959, and 15th-century Casa de Diego Velázquez, the oldest standing house in Cuba. Enjoy picturesque views of the city and refreshments from the rooftop terrace of the illustrious Hotel Casa Granda. Visit the expansive Cementerio Santa Ifigenia, the grandiose final resting place of Cuban national hero and important Latin American literature figure José Martí; Emilio Bacardí Moreau, known for his namesake rum; and Compay Segundo, guitarist of the Buena Vista Social Club.

After lunch on board the ship, view imposing Revolution Square and historic San Juan Hill, a pivotal site during the Spanish-American War. Tour the Casa del Caribe, a vibrant, multifaceted institute that celebrates Afro-Cuban music, dance, and culture. See the original Bacardí rum factory, first opened in 1868, and enjoy a traditional Cuban rum tasting. (B,L,D)

Day 4 — Santiago de Cuba

From Santiago de Cuba, travel to the Basílica de Nuestra Señora del Cobre to visit La Virgen de la Caridad (Our Lady of Charity), the patron saint of Cuba, a brilliant shrine and Cuba’s most sacred pilgrimage site. Tour the holy basilica, where Pope Francis recently visited, and listen to the captivating legend behind this revered shrine. Walk through the lush Jardín de los Helechos, featuring over 350 species of ferns and 90 types of orchids. Return to the ship for lunch, then enjoy an afternoon at leisure in Santiago de Cuba. (B,L,D)

Day 5 — Cruising the Caribbean Sea

Enjoy informative onboard discussions and lectures about Cuban history and culture while at sea. (B,L,D)

Day 6 — Trinidad

Developed from the wealth of the sugar industry in the 19th century, World Heritage-designated Trinidad retains much of its colonial charm, with terra-cotta tiled roofs, pastel-hued houses, cobblestone streets and ornate tiled courtyards. Walk through 18th-century Plaza Mayor, and visit the neoclassical Museo Romántico and Palacio Cantero, as well as a museum showcasing the history of Trinidad’s residents. (B,L,D)

Day 7 — Cienfuegos for Santa Clara

Known as the “Pearl of the South,” the World Heritage-designated colonial harbor city of Cienfuegos was founded in 1819 by French settlers from Louisiana and Bordeaux while located in a Spanish territory, which has made for a fascinating blend of history and local culture today. From Cienfuegos, travel to Santa Clara, the gateway to Cuba’s historically and agriculturally rich central region. Visit a Casa de Abuelos for a unique opportunity to learn more about social welfare in Cuba from the active senior citizen residents and staff. Santa Clara, long associated with Ernesto “Che” Guevara, has been shaped by the most prestigious university outside Havana and features one of the country’s most spectacular grand colonial theaters constructed in 1885. See the beautiful Teatro La Caridad, where famed musicians such as Enrico Caruso once performed, and visit the impressive Che Guevara Monument and the History Museum of the Revolution. This evening, attend the captain’s farewell reception. (B,L,R,D)

Day 8 — Cienfuegos and Havana

Disembark this morning in Cienfuegos. Once a trading port for sugar cane, coffee, and tobacco, this attractive colonial port city was built in a neoclassical style from the wealth of these industries, and its original grid layout plan is an incredible example of early urban planning. Visit the eclectic Teatro Tomás Terry, which hosted its first opera in 1890. En route to Havana, enjoy lunch in a local paladar, then visit Finca Vigía, the former home of Ernest Hemingway, affectionately called “Papa” by locals. Here, he wrote The Old Man and the Sea, based on a local fisherman, and For Whom the Bell Tolls. This evening, check into your hotel in Havana, the Melia Habana Hotel. (B,L,D)

Day 9 — Havana

Cuba’s capital, the early 20th-century “Paris of the Caribbean,” remains arguably one of a kind, mixing impressive urban architecture and culture with an earthy, informal vibe and a lively arts and music scene, while retaining a distinctly vintage feel bolstered by the prevalence of 1950s American-made automobiles fondly called “Yank tanks” by the locals who painstakingly maintain them. The Spanish colonial core of Habana Vieja, a World Heritage site, is a colorful neighborhood of winding cobblestone streets, pastel-hued houses and picturesque squares filled with architectural beauty, including the bayside Plaza de Armas, the site where San Cristóbal de la Habana was founded in 1514. Havana’s downtown district of Vedado is a mix of old and new, including the University of Havana, the pre-revolutionary Capitolio reminiscent of the U.S. Capitol, the iconic Malecón (oceanfront promenade) and the legendary Hotel Nacional de Cuba. See Revolution Square, where Fidel Castro gave his famous eight-hour May Day speeches. Visit the community of Jaimanitas, home to the Hemingway Marina and one of Cuba’s best-known artists, José Rodríguez Fuster, a sculptor and painter whose distinct works of art inspired Antoni Gaudí. (B,L,R,D)

Day 10 — Havana, Pinar del Río, Viñales Valley

The striking Viñales Valley in Cuba’s westernmost province of Pinar del Río is a designated World Heritage site. Known for its natural beauty, the valley is a much photographed and painted 270-square-mile plain surrounded by limestone karst hills called mogotes. The farmland here is among Cuba’s richest, and the ancient agricultural practices produce robust coffee and some of the world’s best tobacco, products central to Cuban history and identity. (B,L,D)

Day 11 — Depart Havana for U.S.

Check out of the hotel and transfer to the airport for your return flight to the U.S. (B)

Included meals are denoted as follows: Breakfast (B), Lunch (L), Reception (R), Dinner (D)