NEW TRIP
Cuba is an enchanting outpost with a quirky mix of colonial grandeur, revolutionary politics, energetic music, and a gorgeous tropical landscape. We’ll dig deep into the island’s unique culture as we meet artists, musicians, dancers, historians, and people from all walks of life. Our journey brings us from Havana to the colonial cities of Cienfuegos and Trinidad, both UNESCO World Heritage Sites. In Havana, we enjoy private music performances, visit Hemingway’s former estate, and stroll the cobbled plazas of Havana Vieja. We’ll then head across the island to Cienfuegos and charming colonial Trinidad, with its village feel and red-tiled rooftops. Come along for a journey full of music, history, discovery, and warm Cuban hospitality.
Arrive: Havana, Cuba
Depart: Santa Clara
In Havana, we’ll take a walking tour with local architectural historian Ayleen Robainas, who calls Havana “a living museum.” Architectural landmarks in Havana are many, and include the monument dedicated to Cuban national hero José Martí and the grandiose Capitolio Nacional, built in 1929. At La Casa del Son, a popular dance school, we’ll be introduced to Cuban dance styles by a troupe of professional dancers. Later, we are joined by art historian Nahela Hechavarría at the Museo de Bellas Artes, dedicated exclusively to Cuban art.
We’ll visit La Finca Vigia, the house once owned by Ernest Hemingway, then tour the Instituto Superior de Arte, which has shaped the Cuban contemporary art scene since 1981. It’s housed in the former Havana Country Club, once a place for the elite of pre-Revolutionary Cuba. In Havana Vieja (Old Havana), with its mix of architectural styles dating to the 16th century, we’ll walk the tree-lined Plaza de Armas, once the political epicenter of Cuba, lined by historic structures including the Palacio de los Capitanes Generales, former residence of Cuba’s Spanish governors. We’ll also stroll Calle Obispo, with its art galleries and music venues.
Driving across the island to historic Cienfuegos, we enjoy a private performance by Cantores de Cienfuegos, an award-winning choir, then continue to Trinidad, Cuba’s colonial gem, founded in 1514. This tiny village has a charming ambiance all its own. We’ll stroll the streets past plazas and pastel-colored houses and hear the live music that fills the air. Outside Trinidad, we tour a sugar plantation, hike to the natural pool below the Salto Rocio waterfall, and visit Ancon Beach. We depart Day 8 via Santa Clara, where we’ll visit the small home of famed revolutionary Ché Guevara, now a museum.
Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.
You must have a valid passport to enter Cuba. Be sure you check the expiration date of your passport to make sure you have at least 6 months before it expires.
Cuba requires that all arriving travelers have a Tourist Card, a.k.a.Cuban visa, officially called a “Tarjeta del Turista,” to enter the country. This visa is to be purchased for all non-Cuban born travelers. As of 2025 Cuba has transitioned to the use of E-Visas (electronic visas), replacing the physical tourist cards. US travelers may apply for their Cuban Electronic Visa online. The cost ranges from $50 USD to $100 USD (including processing fees).
US travelers to Cuba also need to fill out a D'Viajeros form (Customs & Health Declaration Form) which you can complete online starting seven days prior to your departure.
You must have travel insurance that is valid in Cuba. Note that only certain insurance companies cover travel to Cuba.
You'll also need a Letter of Authorization for Travel to Cuba, which Wilderness Travel will supply and which you'll present to US customs upon your return to the States.
Read more about what you need to legally travel to Cuba.
Our Area Specialists know every detail about our tours. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!
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With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult.