A backseat tour of Havana, Cuba

More specifically, from a 1955 Cadillac El Dorado convertible

The first reaction Punky and I had upon booking a cruise to Havana, Cuba over Thanksgiving weekend was of slight disbelief.  After all, it still hasn’t been that long since travel restrictions had been loosened allowing Americans to visit more freely.  The second reaction was probably of slight uncertainty.  So, Royal Caribbean’s Majesty of the Seas will be docked in Havana for a day and a half.  What do we do once we get there?

Fortunately, after significant research on our guided tour options, Punky suggested we get in touch with Old Car Tours, one of the government-authorized private travel companies, to book a day-long “educational people to people” tour of Havana.  

The booking process for Old Car Tours is remarkably easy.  You go online, select your tour (ours was a 6-hour city tour of Havana), choose whether you want just a driver or a driver and a personal tour guide, and then you get to choose the classic car you’d prefer to take your tour in.  And there are plenty to choose from.  Punky eventually decided on a 1955 Cadillac El Dorado red convertible.  We clicked on all our choices and waited for an email confirmation. 

We were pleasantly surprised to hear back from the manager the next morning, who confirmed the date and time and told us where to meet the driver.  The whole process required a small leap of faith since we booked so far ahead, and there was no way to pay in advance.  Because of government restrictions, these tours are cash only, using the Cuban convertible peso, the country’s official tourist currency which conveniently exchanges close to a $1 to 1CUC rate.

Fast forward to Thanksgiving Day, and we’re fresh off the boat, through customs faster than expected and eager to get started on our tour.  Again, due to government restrictions, the tour operator could not meet us directly across from the cruise port, so we took a left and walked a couple of blocks until we reached the Russian Orthodox church, recognizable by its golden domes.    

And sure enough, they were waiting for us, as well as many more similar-minded tourists.  And although we were a half hour early, the greeter identified us, confirmed our tour and connected us with our driver. 

After a few cell phone calls and a short wait, our driver Rainier arrived, greeted us warmly (to be fair, he greeted everyone warmly all day long … he seemed very popular, and with his exuberant personality it’s easy to understand why), seated us in our convertible … 

… and we were off to pick up Jorge, our tour guide for the day.

The first leg of our trip was just a preview of what was to come.  Sun out, top down, and sea breezes forcing me to hold onto my hat as we drove up the Avenue Del Puerto Desamparados.  In a sense, we were driving into a bygone era, and the views of the other side of the harbor were fantastic.

We soon turned inward down one of the main thoroughfares of the city to pick up our driver.  We stopped, in what I would eventually map out as the Vedado neighborhood, at what appeared to be a parking lot for a condo building with substantial recreational area adjacent to it.  Here we met Jorge, who like Rainier was very friendly, personable and exuberant.  He asked us if there were any specific places we wanted to go today.  We didn’t care; all we asked was for him to show us what he though we should see.  He recommended we start at the Plaza de la Revolucion, or Revolution Square, just minutes away.    

As one might expect, Revolution Square is a pretty expansive area surrounded by several government buildings.  Fidel Castro once held a rally here attended by more than a million people.  The Rolling Stones matched that attendance with a free concert. 

Two of the government buildings are the Ministries of the Interior (left) and Communications (right).  You might recognize Che Guevera on the left.  The guy on the right is not Castro, as I first thought.  Instead, it’s fellow revolutionary Camilo Cienfuegos, and the slogan translates to, “You’re doing fine, Fidel.”  

On the other side of what is just about the widest street I’ve every crossed in my life is the José Marti Memorial, the centerpiece of Revolution Square.  A statue of Cuba’s national hero fronts a five-sided obelisk that, by law, stands as the tallest structure in Havana.   A museum is inside the museum, but the observation desk inside the top of the tower is what really makes this a must-see attraction, as Jorge pointed out. 

Here’s the view looking south from the Memorial …

… and here’s the view looking north toward the ocean.  

With a fresh perspective of how large Havana truly is, Jorge was ready to lead us to our next destination.  We circled back to where he had been picked up, then onto another main thoroughfare which took us very near his home.  He told us his desire to one day open an Airbnb out of his home; we were already convinced we’d stay there if he did. 

At the end of the road, we turned left again on the famous Malecon, Havana’s signature boulevard that hugs the shoreline for miles. 

The views just got better and better with each passing mile.

Moving further on up the road, as the Malecon turns into Avenida 5ta (5^th Avenue), we passed through the Miramar district, known for its luxury shopping boutiques and 50s-style mansions which today serve as many other nations’ embassies.  Even further, we were driven through the even more high-rent district known as Biltmore neighborhood, passing by Havana’s own Coney Island amusement park, yacht clubs and gated communities. Yes, this is still Havana, Cuba. 

Finally, nestled between 5^th Avenue and the ocean and very near the Hemingway Marina, we were transported into the surreal neighborhood known as Fusterlandia.  The entire neighborhood is a living testament to folk art phenom Jose Fuster.  We spent considerable time there exploring and shopping, and to really do the experience justice, I’ll feature Fusterlandia in a future blog post of its own. 

After Fusterlandia, we were driven back into a largely residential section of Havana to a paladar named Buenaventura, a lunch spot which apparently gets a lot of business from Old Car Tours guides.  Paladares are essentially family-run restaurants which are operated out of the home; therefore, the Cuban government permits them.  It was an outstanding choice, of course, and another experience best explored in a future blog post.

After a lengthy lunch which included many mojitos, our guides must have figured it was the perfect time to drive us through one of their city parks, which also happens to technically be a rain forest.  

All I know is there’s no way to adequately describe being escorted through greenery like this at a leisurely pace in the back of a 1950s Cadillac convertible.

Once we were through the park, we cruised back toward the Malecon to put us into position to cruise back toward downtown on Havana’s premier promenade, Paseo de Prado (aka Paseo de Marti).  As we cruised the Malecon in a different direction than before, we couldn’t help but notice the Hotel Nacional, which was the “it” place to stay in the city in the 1930s.  If you were wealthy, a celebrity, or had mob ties, chances are you hung out here.  And, from all appearances, it's still a fascinating destination all by itself.

If you love architecture, old buildings, and fantastic city views, the Prado is your boulevard.  It’s also roaring with activity.

Our drive down the boulevard ended with an excellent view of Havana’s El Capitolio, Cuba’s national capitol building.

But our tour of downtown wasn’t quite over yet.  Just a couple of blocks over from the Prado, we passed by Bar Floridita, made famous by Ernest Hemingway because he loved their daiquiris so much.  I was tempted to ask if we could stop, but the effects of the mojitos at lunch were still quite apparent.   

Just a couple blocks past Bar Floridita, we saw the original Bacardi Building.  Built in 1930, not only was it the headquarters for Bacardi rum until 1960, it was once Havana’s tallest building.  

Before we left downtown for our final stop on our tour, we stopped to reflect on our journey so far.

To get to our last stop required a memorable drive through an impressive tunnel under the Canal de Entrada between the harbor and the Atlantic Ocean.  While I was impressed by the tunnel. I think Punky kept her eyes closed. 

Once we reached the other side, however, the views of the city were pretty remarkable. 

We had reached Castillo De Los Tres Reyes Del Morro, built to protect the harbor and city from pirates, invaders and other scoundrels. 

It’s a beautiful place to walk around and feel the ocean air, and the structure itself is pretty amazing, considering how it was built into the surrounding rock and is more than 400 years old.

 

Jorge also though it was a perfect spot for a final photo opportunity with the city in the background. 

At the end of the day (literally), the personalized tour we had with Jorge and Rainier from the backseat of our convertible was priceless.  We met some great people from whom we learned so much about their culture and their great city.  It was everything travel should be – unforgettable memories that broaden your view of the world.  Anyone who visits Havana, Cuba, owes it to themselves to take this kind of tour.