For all you’ve heard about life in post-revolution Cuba, one of the country’s great surprises is how much of its pre-Castro history has been preserved — and how that past and present coexist today. This fascinating expedition includes the colorful colonial cities of Trinidad and Cienfuegos, where you explore cobblestoned streetscapes, walk in lush mountains and snorkel on the tropical coral reef in the Bay of Pigs. In Havana, you wander in the 500-year-old city and out to Hemingway’s home. Throughout, you’ll interact closely with coffee-growers, artists, dancers, historians, and everyday Cubans from all walks of life. Ultimately, you’ll gain a sense of Cuba from its sugarcane-fueled colonial days right up to the latest moment. And you will be rewarded with an engaging, well-rounded understanding of Cuba that’s second to none.
Days 1-4 – HAVANA AND THE BAY OF PIGS
Your week of fascinating insights begins at a local market where you can chat with the locals as they shop. At Fusterlandia, you meet the artists who founded a neighborhood project that has filled the streets with vivid murals. Then you head out for a walking exploration of Havana Vieja (Old Havana) with a local historian and sip a daiquiri at one of Hemingway's favorites bars.
You’ll be welcomed into a traditional cigar-making factory where a friend who is an aficionado fills you in on the role of the trade-in Cuban life. Then you get an up-close look at Cuba-U.S. relations and the Revolution from the U.S.S. Maine to Hotel Nacional. Later, meet the husband-and-wife team whose independent small business specializes in restoring classic cars. Then their craftsmen take you for a tail-finned spin through the streets of Havana.
Throughout, you’ll cook with a Cuban chef, visit a local private Afro-Cuban dance company, chat with a photojournalist who documented Castro’s life, and meet local artists alongside an art curator. Your time in Havana is capped with a visit to Finca Vigia, Ernest Hemingway’s Cuban home that is now a museum.
En route to Trinidad, you’ll stop at the Bay of Pigs for a chance to snorkel on its pristine coral reef.
DAYS 4-6 – TRINIDAD AND CIENFUEGOS
In the Valley of the Sugar Mills, you get an up-close, guided look at the culture and politics of the 19th-century sugar trade. A local journalist leads you on a visit of 500-year-old Trinidad, and you get a salsa lesson at a private dance studio.
Out in the Escambray Mountains near Trinidad, the next generation of a family of coffee-growers welcomes you to their plantation to see how coffee is grown and processed and to share a tasting with you. A variety of other activities take you to Trinidad’s lively outdoor dance scene, a rum tasting, and leisurely evening strolls in the classic Caribbean settings of Trinidad and Cienfuegos.
DAY 7 – CIENFUEGOS
On your final morning, you join a local historian for a personal look at Cienfuegos, the pastel city known as the “Pearl of the South.” Midday, you will reach Havana for your homebound flight.
Starting Point:Havana – 10:00 am – Lobby of first night's accommodation
Ending Point:Havana – 4:00 pm – José Martí Airport
Dates & Prices
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Select our “Family Departure” to travel with other families.
- 6 breakfasts, 6 lunches, and 4 dinners
- Full-time experienced guide(s) who are with you throughout the trip and handle behind-the-scenes logistics
- Admissions to tastings, historic sites and other scheduled events as noted in the detailed daily itinerary
- Gratuities for hotels, meals, and baggage
- All land transportation during the trip
Above & Beyond Benefits
- When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.
Privileged Access Events
- One-of-a-kind access to remarkable people, places and activities arranged just for you.