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 84 reviews

Travel Review: Luxury Cuba Vacation, Havana, Trinidad, Cienfuegos, 1-Week Tour
Our trip through our travel company was simply wonderful. While my husband had been to Cuba, the rest of our family and the family we were traveling with, had not and we didn't know what to expect. But from the earliest moments of our arrival right through our departure, our travel specialist made us feel so welcome; we couldn't have asked for a more professional, experienced guide to take us through the beauty, contrasts and contradictions that define Cuba past, present and future. He is smart, funny, resourceful, thoughtful and accommodating. Not only did he engage us (and respond to a never-ending stream of questions), he hit it off with our teenage sons, which made the trip so meaningful for them. They proudly consider him a friend, as do we.It's easy to praise a guide when things go smoothly, but the real measure of the individual is how they handle things that deviate from the expected.  In our case it was our requests for schedule adjustments, but most significantly, it was when one of our cars broke down en route to Cienfuegos. Our travel specialist and the drivers were on top of it, managing every detail calmly and effortlessly.  Our new driver and his '54 Chevy arrived about a half hour later,; what could have been a disaster became an unexpected adventure.  And I do want to give a huge shout-out to our drivers, a wonderful and accommodating team of drivers. We loved the structure and content of our itinerary, and appreciate your efforts to include a visit to a synagogue in Havana. Also, the homes we stayed in and our hosts were lovely, and the accommodations struck the right chord for our Cuban experience.  As for the food, we never expected such wonderful meals in such great settings.  Our one piece of advice is that the food is so abundant, people should consider sharing meals.  Bottom line: we loved Cuba, and in large measure that's due to the wonderful team you have on the ground -- professional, smart and capable.  We're recommending Zicasso and our travel company to friends and we can't wait to return.

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Luxury Cuba Vacation Review: Havana, Ceinfuegos, Drive In Convertible American Classic, Dance & Music

Our travel planner was great in organizing the trip, I am glad we stayed 50% in hotels and rest in Casas. The bathrooms in Casa in Ceinfugeous was gloomy and had a smell - thank god it was only one night stay. Glad we stayed 4 nights in Havana instead of 3 since there was so much to see in Havana. Glad stayed in Ceinfugeous for one night only on way to pink flamingoes and water falls.The mob tour (which I wanted) was a slight dissappointment, I expected more than seeing lobbies of hotels related to mobs with just pictures. Unfortunately the night tour (nothing happens before 11 pm) would have been great if we were not so tired - we left the tour at 10:30 pm since we were sleepy.The tour guides (very knowledgeable) and drivers were awesome. organization was seamless. overall a good trip

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

We were in Cuba for 10 days. One of the most important things for me for this trip was being able to visit the Cuba National Ballet either as a performance or more desirably, in rehearsal. I'm a choreographer and this was a main reason to visit Cuba. This tour company was the only agency that said they could make that happen. They not only arranged it, it happened to be a fantastic full company rehearsal. Then since they knew about my and my husband's interest in dance and the arts they made that a key point of the experience. I can't say enough about the wonderful encounters we had with dance performances and meeting artists. Everything went smoothly. If there was any issue what so ever, it was handled immediately and without fuss. We felt completely taken care of and that our interests and needs were very important to them. The guides went above and beyond their role. One helped us find the home of a friend who had to leave Cuba 50 years ago. The guide then followed up and found a long lost relative as well. It was a touching and emotional experience for all of us. This I will never forget. This was not a vacation as much as it was a trip to learn and immerse in another culture. This trip was that and then some. We went to places that tourist never go and that was only possible through the tour company who has in-depth knowledge of Cuba and also because of their incredible team of guides. 

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

I did have some concerns as I only found you through the internet and some brief research of reviews.  However, the entire experience was very tight and well thought out.  The landing experience set the bar.  The apartment looked a little shady from the outside but was an amazing place to spend our time in Cuba.  Breakfast in the morning and having the apartment cleaned up while we were out was an unexpected luxury.  All your people were professional and accommodating.  An action pack itinerary made our Cuba experience full and expansive.  Our favorite time was the Horseback ride/cigar plantation/rum adventure.  We also very much enjoyed our time with the rum and cigar expert at the hotel in Havana.  Tell your wife that the art tour was fantastic as she gave us both an art history and Cuban cultural history all-in-one.  To keep the attention of two college students for 2.5 hours is pretty impressive.  My wife an I did not buy a painting at the artist tour but we did buy a painting of Fuster and met him and got a picture with him & I and the painting.  Thank you for taking in all the questions before hand and making sure we had a great Cuban experience.  It truly was VIP.  If you ever travel to the Detroit area look me up.With appreciation,-Tom & Ann Marie

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Travel Review: Cuba Family Vacation, Trinidad, Havana, Hiking, Horseback Riding, Scuba & Snorkeling, Bat Caves, Dance & Music

Our family of 5 adults loved our trip to Cuba.  We experienced beautiful nature through hiking, snorkeling, scuba diving, and horse back riding.  We learned about Cuban history and culture from our knowledgeable guide while visiting colorful Havana and Trinidad.  We saw talented dancers and heard fun music. 

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Customizable Itinerary

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

28,000+ Verified Traveler Reviews