In December of 1956, Fidel Castro, Che Guevara, and 80 other revolutionaries sailed a small yacht called Granma from Mexico to the shores of Cuba. Three years later, the corrupt miltary dictator Batista was ousted from power, which led to a 50 year period of rule under Fidel Castro until 2006, when he stepped down and relinquished power to his brother, Raul. The complicated and often contradictory nature of Cuban history, particularly in the last half of the twentieth century, has left it in what many believe to be a “time-warp,” with dilapitaded buildings running along the shorelines of Havana, and classic American cars rolling through its streets. Yet, Cuba is a vibrant country, filled with some of most open and welcoming people I have met on my travels.
Thanks to the recent easing of travel restrictions to Cuba, Americans can now travel there under 12 categories, one of which includes “people to people- educational activities” and one of which is “professional research”. With the introduction of direct flights from New York, I knew the time to go was now.
Along the Malecon in Havana
After a short flight from New York, we arrived in Havana in the afternoon, breezed through customs, and waited outside for our driver to pick us up. When visiting Cuba, you have two options for accomodations; expensive colonial era hotels, or Casa particulares. Over the last few years, the Cuban government has allowed people to engage in limited forms of free-enterprise such as renting out rooms in their houses, and opening up private restaurants. For around 20–50 dollars, you can stay with a Cuban family and get a cultural immersion experience that would not be available to you if you chose to stay in hotels. Before we had left for Cuba, I had arranged three houses for accomodations through Airbnb, although if you were to just show up, there are thousands of Casas in Havana alone; you would have no problem finding one. Actually, this wound up happening to us as the women I had arranged to stay with emailed me the night before we left to cancel, but arranged for us to stay with her friend, and sent a driver to the airport to pick us up.
As we drove through the outer, rundown barrios that mark the space between central Havana and the airport, with crystal clear, Caribbean skies over head, our driver was quite candid about US/Cuba relations. He told us that since the US and Cuba started to normalize relations, there hasn’t been that much of an increase in American tourism. He seemed frustrated that there still existed any limitations, and told us that if the US and Cuba were to completely normalize relations “everyone would benefit, except for five assholes” alluding to Marco Rubio and other Cuban-American US Senators.
Although I enjoyed our candid cab ride, I was excited when we finally arrived into Central Havana. All the cliches and stereotypes you hear about Havana; old cars, dilapidated buildings, etc, are true, but there is so much more to this aging beauty they call the “Jewel of the Caribbean”
After a little bit of a fiasco with our first Casa, we asked our driver if he could find us a place to stay closer to Havana Vieja; the old, cobblestoned streets of Havana that has been declared a Unesco World Heritage site. After many phone calls, he finally found us a room located right on Obispo, a main tourist thoroughfare in the older part of the city.
We were greeted on the street by Daisy, a Cuban Abuela whose daughter, Mary Diaz, rents out three rooms just up the stairs. With a perfect location and welcoming family, we threw down our bags and headed out to explore the busy streets of Old Havana. We made our way over to the Plaza de la Catedral first. Home of the Catedral de San Cristobal, the cobblestone plaza exudes all the old world charm of European colonialism.

After strolling around a bit, we decided to stop for lunch at one of the many cafes with outdoor seating. Trying to avoid an overpriced tourist trap, we opted for a restuarant a block off the plaza. While enjoying a simple meal of chicken and rice, washed down with a mojito, we were suddenly serenaded by one of the local bands that travel from restuarant to restuarant trying to make some cash. As Cuba has two currencies, one for the locals and one for the tourists, to be able to earn the CUC (which is a one to one conversion rate with the US dollar), is a great way for Cubans to make a little extra spending money. Through their food and healthcare are provided for, free-enterprise capitalism is a long ways off, but the recent opening up of restrictions has allowed some, particularly those in the tourism industry, to make a decent living.
From lunch, we found our way over to La Bodeguita del Medio, one of the handful of bars made famous by Ernest Hemingway, who spent the last few years of his life enjoying the many pleasantries of this Caribbean Jem. Allegedly, here is where Hemingway preferred his mojito, and La Floridita, another touristed bar on the Hemingway trail, is where he enjoyed his daiquiris. In fact, it is said that Mojitos were first invented here in 1942. Yet, Hemingway is not the only famous patron of La Bodeguita del Medio. Infamous Chillean president Salvador Allende also visitied, along with many other famous politicians, celebrities, and writers.
We hopped up to the bar and grabbed two bar stools, just as the slew of day-trippers had to get back to their cruises. Even if the overpriced mojito was not the best I’ve ever had, the atmosphere and history of the place is worth it, if you can get there when there aren’t hoards of Hemingway groupies waiting to get inside.



At this point in the day, and what has become a custom for our first day arriving in other countries, we were starting to get a little sloshed. With no real agenda, other than a list of Hemingway sites I wanted to check off, we strolled the streets of Havana Viega, hopping in and out of bars. Along the way, we noticed that many places were being cleaned up or restored, likely to make it more presentable to the increasing tourism boom that has ensued in the last 10 years.

After strolling around a bit, we walked over to the Plaza de Armas, before stumbling upon the Hotel Ambos Mundas, also known as “the Hemingway Hotel” because he famoulsly penned parts of For Whom the Bell Tolls here on the 5th floor. Feeding my Hemingway obsession, we saddled up to the piano bar in the lobby first, though it wasn’t very interesting or fun. We soon realized however, that one could ride the iron-gated elevator up to the top floor for one of the best views of the city, and oh yeah, there’s a bar up there as well.

After another drink, this time a Cuba Libre, we strolled around some more, taking in the classic American cars and rundown buildings, eventually finding our way over to the Malecon, undoubtedly my favorite place in Havana.


A sea-wall turned pedestrian stroll, the Malecon runs along the Northern part of Havana, with old, faded and worn classical buildings on one side, and Miami just to the North. As we strolled along, with the sun-setting in the distance, 1957 Chevys cruising down the highway, and waves crashing up against the wall, we came across many Cubans fishing, laughing, playing music, and just, simply, enjoyng life.


- Sunset along the Malecon
The next day we made our way to the Cathedral of Saint Francis for Palm Sunday. When we had asked around the previous day if anyone knew what time mass was, most people had no idea, and clearly had no intention of attending either. For a country that endured over 400 years of Spanish control, this seemed a bit odd. It was Castro’s revolution however, which diminished the Catholic Church in Cuba, railing against any form of organized religion. Not knowing what time to be there, we headed towards the church and were met outside by the priest and a group of parishioners holding their palms in prayer. When they were done, the priest walked over, put his arm on my shoulder and welcomed us inside for mass.

In the afternoon, we made our way to the Museum of the Revolution, housed in the former Presidential Palace where Batista lived before Fidel and the rebels ousted him in 1959. As a history teacher, this place was fascinating, with several exhibits that really struck out, such as the typewriter that Castro penned his famous “History will Absolve Me” speech on, and life-size effigies of Che Guevara and Camilo Cienfuegos hiding out in the Sierra Maestro mountains. Not to mention the bullet holes in the building. For those of you who are not familiar with the history, here is the run down. During the 1950s, General Batista was a corrupt military dictator backed by the US government and with ties to the American Mafia, who was making a killing in Havana. On July 26th, 1953 a group of rebels under the leadership of Fidel Castro, stormed the Presidential Palace (the musuem today), only to have Batista sneak out the back door. Many of the rebels were killed or imprisoned, with Castro earning a name for himself as a result. In 1955, in an effort to appease his critics, Batista granted amnesty to political prisoners, and Castro was released from prison. Fearing he would be assasinated, Castro fled to Mexico where he met “Che” Ernesto Guevara; an Argentinian doctor who was committed to freeing Latin America from European and American imperialism. In 1956, Castro, his brother Raul (now the leader of Cuba) and Che sailed the Granma yacht to the shores of Cuba to begin what we now call the Communist Revolution in Cuba. The “landing” was a disaster however, with only 15 rebels surviving and having to flee into the Sierra Maestro mountains, where they survived and fought for another two years until January 1st, 1959, when Batista, seeing the writing on the wall, fled Cuba for the Dominican Republic.



Perhaps the most intersting thing we came across however came at the end of the exhibit, where there is the “Hall of Cretons”, a wall with 4 characatures of Batista, Reagan, Bush Senior, and “W”. Clearly, the foreign policies of these three US presidents has served as useful propaganda for the Castro regime.

From the museum, we headed down towards the Malecon to walk towards Central Havana so we could catch the African drummers at “Salvador Alley”. Unfortunately, we arrived after it ended. Realizing our money was depreciating faster than we had expected, we approached two Americans crossing the street and asked them if they wanted to split a cab with us to the Plaza of the Revolucion, but they were not going in that direction. In one of those weird quirks of travel, we would meet them again in another city where we shared a Casa with them and, eventually, split a cab ride to Trinidad. The Plaza of the Revolution, though interesting because of its revolutionary connection, is a rather depressing, Soviet style, open plaza with Che’s face planted on the Ministry of the Interior Building overlooking it. Recently, they have added Cienfuegos’ face as well.


Underwhelmed by the plaza, we hired another cab to take us back to Old Havana, which happened to drop us off at La Floridita, perhaps the most famous of all the Hemingway bars. Hemingway famously said “Mi mojito en La Bodeguita del Medio, mi daiquiri en la Floridita”. The bar, fully aware of the draw of Hemingway to tourists, has this quote on the sign outside, as well as a plaque inside. Although it was crowded, we managed to find two seats at the bar, conveniently right next to the life-size Hemingway statue that tourists (myself included) pour in just to snap their picture with.


After sipping a daiquiri, which although overpriced, was quite good, we freshened up back at the Casa then headed back into Central Havana to have a drink at the Hotel Nacional, a famous hotel that served for a convenient meeting place for the mafia during the 1950s. Perched upon a hill overlooking the Malecon, the outside terrace bar in the back is supposed to be a great place to catch the sunset with a mojito. We wouldn’t’ know however, because it was here where we realized that we (and I mean me) didn’t bring enough US cash with us for the week. Banking (no pun intended) on being able to use our American Credit cards at fancy resturants and hotels (like this one), we went into a bit of a panic when they said it was not possible to use them anywhere. We opted to forego the $7 mojito and tried to find a bank or ATM or internet that might be able to help us. We were told by a friendly Cuban trying to help us that the ATM in the Hotel Libre (the former Hilton) would be able to work with our banks, but this did not pan out. Finally, I turned on my mobile service and called my credit card asking them how to get a cash advance in Cuba, to which the women confidently explained I just needed to bring my passport to a Westrn Union. Not caring a bit about fees and percentages, and feeling a bit confident we would be able to get money the next day (it was late at this point), we decided we would be okay and if worse came to worse, we would just have to stick to a budget.
We walked down by the Malecon again, only this time we came across a memorial to the sinking of the USS Maine, the catalyst for the US involvement in the Spanish American War. Apparently, the memorial used to have an eagle on top of it, but this was knocked off by rebels during the revolution. A brief history: In the 11th hour of the Cuban’s struggle for independence from Spain, the US decided to intervene on their behalf, largely due to this incident. The USS Maine, sittiting in Havana’s harbor in 1898 mysteriously exploded, giving America the ammunition it needed to join the war. At the time, many in the US believed it was the Spanish who blew up the ship, although some historians contend it was the Cubans themselves, trying to bring the US into the war. One other theory suggests that it was an explosion from within the ship that caused it. To this day, the Spanish government officially denies its involvement in the incident. Whatever the truth is, the sinking of the Maine officially began a bumpy relationship between the US and Cuba, that still exists to this day.



We eventually found a hip (and cheap) restaurant in the Vedado neighborhood for dinner where we met a friendly Swiss who was traveling alone and joined us for conversation. He asked us if we wanted to get icecream with him at Copelia’s; a government-run ice cream place that also serves as an outdoor park where Cubans can socialize freely with one another. With the conversation dragging over ice-chipped, watery vanilla icecream, we decided to grab a beer down the road. La Rampa, a street that connects the Vedado section of Havana with the Malecon, is filled with bars and music clubs, catering to tourists and locals alike. We found a table at Sofia’s and enjoyed some local Cuban music over a beer. As we were heading out of the city early the next day, we wished our Swiss friend safe travels and called it a night.

The next day, our Casa host, Mary, arranged a car to drive us 4 hours to Cienfuegos, a beautiful city along the south shore of Cuba, known for its architecture and beautiful bay. When our driver arrived to pick us up that morning, we walked out to his 1961 Plymouth that was going to drive us straight across Cuba, diesel fumes and all. Along the way, we asked our driver, Coco, if we could stop off at Play Giron which sits along the shore where the botched Bay of Pigs invasion took place. Here, there is a little museum that celebrates the fact that the Cubans were able to fend off the CIA trained Cuban expats from America. With Kennedy refusing to offer full support for the invasion, the Cubans who returned to their mother country hoping to remove Castro from power were left like sitting ducks along the shore. The incident proved to be a blemish on Kennedy’s foreign policy record, and a source of contention between the US and Cuba for years to come.



- Bay of Pigs
- Billboard Propaganda
After we explored the small museum, we went for a quick swim in the water where Michelle, trying to return to the shoreline, fell over a submerged rock, declaring it “the worst amphibian landing since 1961.”
Around 2:30, we headed back to meet Coco so we could arrive in Cienfuegos with enough time for him to make it back to Havana before nightfall. We pulled into the city a little before 5pm and found our Casa along one of the main, pedestrian only thoroughfares in the city. We bidded Coco farewell, and walked up to meet our hosts, Midaiyms and Guillermo; two of the most welcoming people we met in Cuba. Proudly boasting of the nation’s longest Paseo, Cienfuegos suprisingly delighted us with its quiant architecture and impressive sunsets along the bay.


The Communist Revolution in Cuba was meant to transform the country from a colonized victim of American capitalist imperialism to a socialist utopia where everyone was equal and cared for. The realities of this idealistic vision 60 years later are played out in the streets of Havana everyday, but we had yet to explore how the Revolution affected the rest of the country. In my next post, I will explore our brief, but pleasant stay in Cienfuegos, the Unesco world heritage site of Trinidad, and then back to Havana where we bid farewell to rum, cigars, and most importantly, our new found Cuban family.