Cigars, Guitars and Vintage Cars…A Weekend in Cuba!

Cuba is known for many things: classic cars, rum, cigars, and their unique culture to name a few. It was for these reasons and more my daughter and I chose Cuba for the next Gypsy Mama Bear adventure!

Our weekend began in the city of Havana.  It was as if we were taking a step back in time walking around the square in old Havana. We loved how the locals still enjoy sitting around and relaxing on the benches at Plaza de Armas, listening to musicians drift their tunes through the air. With their vintage cars and lack of American influence, the city is full of culture that seems to have been frozen in time.

The first thing we wanted to do was to rent a pink American classic convertible and cruise around Havana. Most of the cars include a driver and an interpreter, and though it can get a bit pricy, it is well worth the cost.

Typically tourists will rent the cars in the morning or evenings, but our interpreter told us if we came back in the afternoon we could rent it at half the cost. This worked out wonderfully for us because there was plenty of local attractions we could experience to fill up our morning.

Gypsy Mama Bear Tip… Don’t bother taking credit/debit cards to the island, they don’t have machines nor do they take them.  There are two standard currencies in Cuba: the Cuban convertible peso (CUC) is one the tourists use.  The value of the CUC to the dollar is 1 to 1.  You will have some exchange/bank fees charged. 

The Cuban Peso (CUP) is used by the residents of Cuba. Tourists probably won’t use CUPs very often unless it is for street food, bus fare or small expenses.  1 CUP is only worth 4 US cents.

The difference between CUC and CUP:  CUC bills do not have faces.  If you receive a bill with a face, return it, you are getting a CUP instead.  Also look for the words ‘pesos convertibles’ at the right of the CUC bill. 

We followed the sound of music and wound up at a small outdoor cafe. We were able to listen to a wonderful Cuban band, sample some local rum, and enjoy a few puffs of a real Cuban cigar. When in Cuba…! My daughter was even able to take part in shaking the maracas while the guitars strummed their enchanting tunes. Our morning activities passed, and it was time for what we had really been looking forward to: cruising around in our classic convertible!

We first asked the interpreter if they would take us to Sloppy Joe’s Historic Bar in Old Havana and they were more than happy to oblige. Be prepared to let them know where you want to go if you want to do something not on their usual agenda, they will be happy to accommodate you. We were keen on going there to get a photo in front of Ernest Hemingway’s favorite hangout. This bar had been closed for 48 years but reopened in 2013.

Our next stop was the Christ of Havana statue.  This large sculpture is the work of Jilma Madera.  It is carved out of 67 blocks of white marble and stands 66 feet high.  The statue has a few unique features you should take notice of. The first is that it was made without eyes to give off the impression that it is watching you from any angle you view it. The second is that though the hands are empty, locals suggest that the placement of the hands represent him holding a cigar in his right hand and a mojito in his left, honoring popular Cuban culture. The statue overlooks the bay of Havana and has a nice view of the city.

For our last stop, we were able to get an up close and personal visit with a deactivated Soviet-made missile at the La Cabana fortress. I remember reading about the Cuban Missile crisis of 1962 so I found it very interesting to see the artifacts from this time period. I appreciated the interpreter’s knowledge and insight on the subject. It is always great to learn new things, especially from those who lived through it.

This Cuban historical visit was a fabulous memory I truly will never forget. The driver gave us a wonderful tour of areas that otherwise would have been too far of a walk to see.

My mom and my kids always loved watching the “I LOVE LUCY” show.  We especially loved the episode with Ricky and Lucy at the Tropicana Night Club. Because of this, we knew had to see this childhood memory in person to make a dream come true.

That evening we were able to see the fabulous Tropicana cabaret show which had more entertainment than I ever expected!  When we arrived, the men were greeted at the door with a Cuban cigar and the women were greeted with a rose.  We were seated at a table with a bottle of Havana rum and chilled champagne waiting for us.  The show was spectacular and I was able to imagine Ricky singing to Lucy as she danced in her Carmen Miranda hat.  As I was day-dreaming about my old-time black and white 60’s tv show, out came the stunningly gorgeous dancers in their fruit hats. We thoroughly enjoyed every minute of this exciting show with its flashy bright lights, Cuban Rum, professional singing, and stunning costumes. DO NOT MISS THIS!!!

As we said goodbye to beautiful Havana, my wish was for it not to be goodbye forever but rather until we visit again…


This beautiful Cuban city is located on Bahia de Cienfuegos, a bay on Cuba’s south coast.   The bay was gorgeous and the water clear blue and glass like. We strolled through Jose’Marti’ park, a paved plaza, surrounded by 19th century buildings. We wandered through the Terry Theatre boasting gold-leaf mosaics.

I loved taking photos of the colorful buildings and all the action on the streets.  I loved seeing all the locals interacting, walking, riding motorcycles, and driving small cars as they all went about their busy day.  I was able to snap a few photos of the “real life” in Cienfuegos on our way to the tobacco factory tour.

The tour was very educational and informative.  We met some of the lovely workers inside the factory, working away at hand rolling cigars for the world to enjoy.  It was incredible how these workers took such painstaking pride in making the perfect cigar.  Each one was made with hand-picked, expertly grown tobacco leaves.  Unfortunately, we weren’t allowed to take photos inside the factory but the guide let us ask the workers questions while they worked. I would highly recommend this tour not only as an interesting stop, but also because of how much Cuban culture you can experience there.

Both Havana and Cienfuegos have unique attractions available to them. I would recommend visiting both cities to get the full Cuban experience. If you don’t have time to visit both, flip a coin! You cannot go wrong with either of them.

We found the locals in both cities very charming and friendly.  Most wanted to engage in conversation and the majority spoke fluent English.  We did not run into many panhandlers or beggars like some countries that we have visited in the past.  We did have locals on occasion approach us to buy cigars. They purposely wanted to engage in conversation with us to lead into selling us cigars or trinkets.   We found out that often the cigars they were trying to sell were “off market” and had fake labels.  We avoided those and purchased a few cigars from one of the government stores at the terminal to take home.

Favorite Gypsy Mama Bear Memory….While wandering around the plaza,  an adorable young local boy about 5 years old ran up to me and wanted to kiss my cheek at the Plaza Vieja.  I asked his mother if he wanted money and she shook her head no and just said “We welcome you to Cuba!” This interaction encapsulated our experience in Cuba. Everyone here was so warm and inviting.

The Cuban culture was as unique and vibrant as we expected it to be, and yet it still managed to exceed our expectations. If you are into experiencing a rich culture, then these two cities should be high on your list. What’s your traveling preference: historic cultures or off the beaten trail adventures?


Find the joy in the journey

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