I had wanted to visit Cuba since the summer of 2005 when my friend Natalie and I were drinking mojitos at a Latin bar along the Mediterranean in Glyfada, Athens, Greece and she was telling me what a fabulous place it was. Americans have always gone to Cuba – just in roundabout and secret ways. I was willing to do that, too – but was excited to be able to join a week-long tour of Havana with Friendly Planet. Sean and I both felt that the time to go was now (or maybe even a year or so ago) before the cruise ships started really pouring in and flooding Havana’s limited infrastructure and restaurants with tourists. While we want to see more of the country, we felt that Havana was changing the fastest and wanted to get a glimpse of history in the making with our first (but not last) trip to this mysterious island.

The flight from Miami was only 40 minutes. As my mother-in-law says of such short flights – “here drink this! We’re landing!” 🙂 Me, being the sap I am and in awe of this tiny country’s resilience, history and completely different economy and government, cried during landing. But hey – American Airlines leaving a U.S. airport and landing in Cuba is definitely a piece of history and one I found made me emotional.

We had absolutely zero issues entering the country. I was beyond surprised as was our entire group. On the drive in from the airport, we passed by small villages and countryside. I spotted writing along a wall that said “Socialismo o Muerte” – Socialism or Death – and wondered if people had written that or if it was done by the government as a form of propaganda. Writings like that were pretty common, as I came to see.

Our first stop was Plaza de la Revolucion and I was again pretty overcome by the history of all that I was seeing and the wonder I felt at actually being there.

“Until victory always” – Che Guevarra

And all the cars! These historic and classic cars were filling the area, serving as taxis to bring in sightseers.

Next up was lunch in what we were told was one of the first “paladares” in Havana. Paladares are privately-owned restaurants and were called such from a Brazilian Soap Opera popular in Cuba that had “Paladar” as the name of a chain of restaurants. Pretty cool how it caught on.

Sean and I didn’t have high expectations for the food and were aware it was going to be more of a “this is what we have” situation but we were pleasantly surprised by this lunch (which was by far our best one). I had a lovely piece of grilled red snapper that was incredibly fresh, and the black beans and rice were incredible. 

After lunch we went to Colon Cemetery, a 140-acre monstrosity in Havana. I have a book of photos of Cuba from the air and this cemetery is beyond huge. It’s over-the-top. And the government keeps it pristine, in accordance with some crazy law from back in the late ’50s/early 60s when fleeing Cubans thought the Revolucion would not last and they could come back home and eventually die and be buried here. A complete waste of resources in a country under embargo, if you ask me. But hey, to each their own. And it was still pretty cool to see and learn about.

Our “casa” – or private, boutique hotel, was located in Central Havana (Centro Habana to locals) and the neighborhood was as I expected – worn down by time and neglect but still showing off a deep soul of beauty, culture and history. The streets were being torn up to replace piping, etc. which, although tough for cars to travel on, was ultimately good for the infrastructure. 

The casa reminded me quite of bit of the traditional Andalusian hotel we stayed at in Granada, Spain last year with lots of beautiful dark wood, unique rooms and open courtyards. The accommodation was MUCH nicer than I was expecting. While older, everything was pristinely clean and had tons of character – and air conditioning! Sean and I had upgraded to a suite and had a large room with a balcony facing the main street, gorgeous stained-glass windows above the tall doors and a soaring ceiling with wood beams.

View from our balcony, with the Malecon (the city’s incredible seafront esplanade) on the horizon.

After a short nap (we had to get up at 5am for our flight!), we wandered out to the Malecon to take in the sea views on one side and line of buildings on the other as we explored the area. We passed by little stores selling eggs and other ration food items – in Cuba the goal of rations is for no one to starve and so for about 50 cents, families get a minimal supply of rice, beans, eggs and chicken. It’s not a lot but it’s a fascinating concept to me and I loved learning about it – and learning the varying opinions other Cubans have about it.

We found a local supermarket and went in to explore. We had been told that there isn’t a lot of choice and that many Cubans rely on money and items brought in from family in the US and other nearby countries. The store reflected that. About 1/3 of it was housewares and toys haphazardly strewn about, another 1/3 was pantry items like pasta, rice, canned goods, and another 1/3 was drinks – water, juice and alcohol. Havana Club rum was so cheap I couldn’t help but hear George Orwell’s descriptions of “Victory Gin” ring through my head. The meat counter had one lone log of bologna. 

We bought some water and rum, then headed back to the casa to change our clothes for our “welcome dinner” and enjoy a mojito in the lobby with our group before heading out.

The restaurant was in Vedado, a slightly more upscale neighborhood on the western side of Havana that is known for its nightlife and beautiful houses. We had a nice meal of a Cuban take on paella and I was again loving the fresh seafood – along with the mojitos. 😉

After dinner, Sean and I decided we wanted to explore more so the bus dropped us off at the stunning and historic Hotel Nacional de Cuba, also in Vedado, and our tour guides gave us directions to a nearby jazz club that started later.

The hotel was amazing – the grounds were lush, there were two different bands playing and the inside was truly like being in a bygone era. So romantic, classy and haunting all at the same time. 

We eventually stumbled onto a bar tucked away called “Churchill’s Bar” and ordered daiquiris from the bartender, along with our first cigar of the trip – a Cohiba!

The jazz club cost us 10 CUCs (Convertible pesos – about $11) and included two drinks. Pretty great deal. It was in the basement of an old building and we grabbed a small table at the front. The music, atmosphere, service and people-watching were all fantastic. What a great first night in Havana!