Retracing the Steps of Cuban History: Havana & Cienfuegos Tour

What to expect on this itinerary
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 to a bygone era. Cuba’s streets tell many stories, each as captivating as the next.
Customizable Itinerary
Havana – The Likes of Which You Have Never Seen
Your heart thumps with excitement as the plane descends onto the runway at Jose Mart International Airport. The high-rises of the contemporary neighborhood of Vedado stand tall against the background of turquoise water from the Atlantic Ocean. The dome of the Capital Building is reminiscent of the United States Capital in Washington D.C., which it was modeled after. The plane lands, and you are about to step into Cuba, a prospect you never could have imagined. Cubans crowd around the exit near baggage claim holding signs for family and friends returning from abroad. Your private transfer greets you at the airport and escorts you to Revolution Square. The stone tower rises over 350 feet above the plaza. At its base stands a large marble figure representing Jose Marti, the father of Cuban independence.
Images of Che Guevara and Camilo Cienfuegos decorate the buildings opposite the tower. Continue to Hotel Nacional de Cuba; a luxury establishment erected in the 1930s. Famous visitors have included Frank Sinatra and Marilyn Monroe. The edifice stands atop a strategic hillside overlooking the Malecón, the famous seaside boulevard wrapping around the edge of Havana. Beneath the hotel is a bunker where Fidel Castro and Che Guevara resided during the Cuban Missile Crisis. A walkway leads to the stone construction burrowed into the hill. Posters explaining the tension between Cuba and America line the walls. You find a map pinpointing the location of Cuban forces and missiles during the crisis.
What's Included:
Havana – Bringing the Past to Life
Havana – History of a Complex Relationship
Havana – Days to Remember
Cienfuegos – Timing of the Story
Cienfuegos – Art and Colonialism
Cienfuegos – Upraising the Farmer
Cienfuegos – Crafting the Story of Cuba
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
$4,300 per person (excluding international flights)
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.
Verified Traveler Reviews
Based on 35 reviews
The trip was wonderful! Everything was so great. I would highly recommend Zicasso’s tour company to anyone traveling to Cuba. Our guide and driver were excellent, and we really loved them. Everything was taken care of, from being picked up at the airport to meals and accommodations. This also included guided tours into dance studios, museums, rum factories, an architectural tour of Old Havana, and more! Again, I would highly recommend our travel company.
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We had a wonderful time in Cuba and our guide, driver, and Zicasso tour director were all very professional and welcoming! We visited beautiful sites, including Havana and Trinidad, and felt we learned something about Cuban culture.
For future travelers, please pack a flashlight, as power can intermittently go out. Cubans are prepared for this and life goes on as normal.
We were well taken care of on this trip and since it was all-inclusive, bringing a lot of extra cash was not necessary. We recommend bringing cash for tips and souvenirs.
Our tour was in a charming 1952 Chevy, equipped with AC and plenty of trunk space. The food was great, especially for seafood lovers, and there were plenty of places to hear live Cuban bands. We highly recommend this tour and this travel agency!
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What a wonderful trip! Zicasso's travel agent and her team were outstanding. The trip was well planned to visit the popular Cuban cities and towns, and included a personal trip to where my son's father was born. All the tours were great. Thank you to our guide and drivers! The accommodations, restaurants, and entertainment were terrific.
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This trip was well worth every penny. Zicasso's tour operator was amazing and paid attention to every last detail. Our drivers and guide were so good. They knew exactly what we needed and wanted, and made sure the trip was perfect every single day. I know this sounds like I am gushing and that it couldn't have been this good, but it truly was!
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After a very shaky start, the trip turned out great. We became alarmed and almost aborted the trip when we were given a translator whose English skills were poor AND no one picked up our friend at the airport which had been prearranged. By the time we had gathered her, it was 4 pm and we were supposed to set off on a 7 hour journey to Trinidad. It didn’t seem wise to embark on such a trip so late in the day. We were also concerned about the “vintage “ cars without seat belts or headrests. If we had been better informed regarding the situation, we would have understood and agreed to this arrangement without question. Cuba is, after all, in economic crisis. Our agent heard our concerns and responded beautifully. She couldn’t do anything about the old cars without safety features but she recommended that we stay the night in Havana. She put us in a fabulous hotel. From then on, the trip was spectacular. She sent a new translator who was fabulous. Our accommodations in Trinidad were just lovely as were the restaurants and activities. The hike could have been better described. It was very difficult. We turned back because we didn’t have enough water or walking sticks. Bay of Pigs was interesting. We would have loved a guided snorkeling tour. I would recommend this group provided they use our translator or equally competent translator and that they upgrade their descriptions of the “vintage “ cars and the outings.
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We had such an amazing family trip, learning about Cuban culture and meeting amazing people along the way. Our Zicasso trip planner and our driver for the week were professional, kind, knowledgeable, and handled all the logistics of the trip with ease. From the places we stayed to the museums, beaches, hikes, and restaurants, we were well taken care of and came away with a truly unforgettable experience.
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