Retracing the Steps of Cuban History: Havana & Cienfuegos Tour

Traditional colonial-style architecture in Cienfuegos, Cuba

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.

Countries Visited

Cuba

Places Visited

Havana, Cienfuegos

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

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:

Tour
Transfer
Accommodation
Day 2

Havana – Bringing the Past to Life

Day 3

Havana – History of a Complex Relationship

Day 4

Havana – Days to Remember

Day 5

Cienfuegos – Timing of the Story

Day 6

Cienfuegos – Art and Colonialism

Day 7

Cienfuegos – Upraising the Farmer

Day 8

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)

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.

4.9

Verified Traveler Reviews

Based on 76 reviews

Travel Review: Luxury Cuba Vacation, Havana, Trinidad, Cienfuegos, 1-Week Tour
"We're recommending Zicasso and our travel company to friends and we can't wait to return."

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"The tour guides (very knowledgeable) and drivers were awesome." 

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Cuba Travel Review: Old Havana, Museums, Rum Factories, Architecture, Beach, Hemingway House, 8 Nights

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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ravel Review: 10 Days in Cuba, Havana, Cienfuegos, Cuba National Ballet, Cooking Classes, Artist & The Arts, Local Culture

"We felt completely taken care of and that our interests and needs were very important to [the tour company]."

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Cuba Review: Havana, Cigar Plantation, Rum Tour, Art History & Culture, Horseback Riding, Luxury 5-Day Trip

"Thank you for taking in all the questions before hand and making sure we had a great Cuban experience.  It truly was VIP." 

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Travel Review: Cuba Family Vacation, Trinidad, Havana, Hiking, Horseback Riding

"We learned about Cuban history and culture from our knowledgeable guide while visiting colorful Havana and Trinidad." 

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Customizable Itinerary

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

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