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.
Havana Jazz Festival: Join us on the Havana Jazz Festival date (below) and enjoy all of the experiences in this itinerary against the backdrop of music throughout your days and evenings in Havana. You’ll also enjoy three ‘only with Classic Journeys’ experiences: sit down for a meal with the director of the Jazz Festival (a personal friend of our guide), a private jazz session with a group of musicians who share with you how they create music, and in-demand tickets for concerts each of the evenings in Havana so you get access to the best performances without having to arrange the details yourself.
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 favorite 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.
Why Choose Classic Journeys
We believe in creating authentic connections by immersing you into the history and culture of a people and place. So we find the most well-connected local guides who share their relationships and knowledge with us. And with them, we handcraft walking tours in cinematic settings that allow you to see the world on foot and at eye level.
It’s why Travel + Leisure magazine has named Classic Journeys as the #1 World’s Best Tour Operator multiple times, and the editors of T+L say, "Classic Journeys provides unbeatable access to experiences around the globe." Here’s what that access means for you every time you travel with us.
- Experience the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the region.
- Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, share their lifelong connections as well as engaging anecdotes about the history and culture of the region.
- Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like Stonehenge so you experience the stone circle when it’s closed to the general public, a guided visit to Zion Narrows that other companies cannot arrange because of larger group sizes, and vineyard walks with a count and countess in Tuscany.
- Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you’re exploring, including rainforest lodges, 16th century villas, and award-winning properties that show up on World’s Best and Gold lists.
- Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us. From gourmet picnics to coveted local restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
- Handcrafted itineraries with all activities included. With our long-term friendships, we know our walking tour regions more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
- Sustainable travel that supports the places you’re visiting. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.
We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour.
- 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.