Cuba: Havana, Cienfuegos & Trinidad

7 DaysStarting at $4,795


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.


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One of "50 Tours of a Lifetime", this is one of the most authentic, innovative, immersive, best-guided, and most sustainable tours.”
National Geographic Traveler


Travel + Leisure magazine has named Classic Journeys as the #1 World's Best Tour Operator multiple times. As the editors of T+L say, "Classic Journeys provides unbeatable access to experiences around the globe."

Here's what that access means for you in the Cuba with Classic Journeys.

  • Join a local historian for a walking exploration of Old Havana and then sip a daiquiri at one of Hemingway's favorites bars.
  • Accept an invitation 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.
  • Meet the husband-and-wife team whose independent small business specializes in restoring classic cars, then join them for a tail-finned spin through the streets of Havana.
  • Cook with a Cuban chef, then chat with a photojournalist who documented Castro’s life, before you visit Finca Vigia, Ernest Hemingway’s Cuban home that is now a museum.
  • Walk along the infamous Bay of Pigs, then see it from a totally different vantage point as you snorkel on its pristine coral reef.
  • Accompany a local journalist on a walking tour of 500-year-old Trinidad, where you also get a salsa lesson at a private dance studio.  
  • In the Escambray Mountains near Trinidad, follow a scenic footpath to meet a family of coffee-growers at their plantation to see how coffee is grown and processed and to share a tasting.
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  • 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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Family Departure

Select our “Family Departure” to travel with other families.

What’s Included

  • 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

Invisible Check-In

  • 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.