Traditional colonial-style architecture in Cienfuegos, Cuba

Retracing the Steps of Cuban History: Havana & Cienfuegos Tour

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Havana, Cienfuegos

Suggested Duration

8 Days

The trepidations of the Cuban Missile Crisis and the Bay of Pigs are tangible memories. The easing of regulations has opened up new doors between the United States and Cuba. Your tour is custom tailored to discover the people and culture of the island nation, at times contrasting the perception of the country only 90 miles off the coast of Florida. Artists paint murals capturing the spirit of Havana. Cienfuegos is filled with pearled French architecture. Colonial buildings in Trinidad harken back...

Customizable Itinerary

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Trip Highlights

  • Discover the Cold War era bunker beneath Hotel Nacional de Cuba
  • Meet with local Cubans, from artists to retirees, to discuss daily life in Cuba
  • Traverse the cobblestone streets and colonial architecture of vibrant Havana and celebrated Trinidad, led by guides specializing in history and architecture
  • Witness the Cuban enterprise first hand by visiting privately owned restaurants, shops, art markets, and a farmers' market
  • Get inspired with a visit to Ernest Hemingway’s restored Cuban Home
  • Collect the diverse stories from Colon Cemetery during a private tour explaining the history and mythology of the grounds
  • Visit the Bay of Pigs Museum at Playa Giron to experience the Cuban perspective of the events in 1961
  • Wander through the expansive Che Guevara memorial in Santa Clara to see the art, mausoleum, and eternal flame commemorating the rebels 

Detailed Description

Cuba and its relationship to the Soviet Union shaped much of American foreign policy during the 1960s until the 1980s. Those who read about the Bay of Pigs and witnessed the Cuban Missile Crisis have very different views of Cuba. Your 8-day tour offers seniors a chance to circumvent government tension and visit the source of Cuban culture, its people. You will immerse yourself in the enthusiasm of Havana, the spirit of Trinidad, and the beauty of Cienfuegos. Artists and writers, musicians and dancers, will all show you how they use their heritage and surroundings as daily inspiration. Dine in private homes and traverse the grandeur of the museums to uncover the true stories of Cuba.

Your senior adventure begins when you arrive at Jose Marti International Airport in Havana. Your private transfer meets you at baggage claim and leads you into the city for an introductory tour. See the monuments at Revolution Square and enter a bunker used by Castro during the Cuban Missile Crisis. The following day, you meet an architect helping with the restoration of Old Havana. He guides you along the cobblestone streets and historic plazas. Later in the day, you visit Havana’s first English language bookstore. Meet with a professor of U.S.-Cuban relations before traversing the gilded halls of the Fine Arts Museum of Havana.

Continue to the Fortaleza de San Carlos de la Cabana to explore the largest fortress in the city. Meet with a local women’s choir for a private performance that also offers you a chance to discuss women’s roles in Cuba. Next, you make your way to Ernest Hemingway’s former residence. If the walls could talk, you could hear endless stories about the famous author. Continue to Colon Cemetery where the mausoleums have beauty tales of their own. Venture to the Zapata Wetlands to see a recreated aboriginal village, along with a nearby crocodile farm. Continue to the Bay of Pigs Museum for a different perspective on the altercation before arriving in Cienfuegos.

You meet with local art students of Cienfuegos, who take inspiration from the smallest details of the city. Once in Trinidad, your guide leads you on a vibrant tour of the colonial town. Meet with local small business owners to learn about what it takes to start a private business in Cuba. Wander through a colorful farmers market. In the city of Santa Clara, you meet with a group of active seniors keen on sharing their lives and lifestyle with you. Tour the city and discover the magnitude of the Che Guevara Memorial and Mausoleum before returning to Cienfuegos. On your final day, your private transfer meets you at the hotel and escorts you to the airport for your flight home, ending your immersive senior’s tour of Cuba.  

Consider browsing our other escorted Cuba tours, and gain further inspiration to perfect your Cuba vacation of a lifetime. 

Starting Price

$3,379 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

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4.98 stars based on 91 reviews.

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