For quite some time Garret had been itching for a chance to go explore one of the more difficult places for Americans…Cuba. Long a sore subject since the JFK Administration, travel restrictions and diplomatic relations are recently on their way to becoming normalized between the US and Cuba. Even cruise ships are part of the equation, with the first American one docking in Havana the week before we got there. Therefore we knew the time was now to see Havana before the American “invasion”, as one Cuban put it to us, inevitably occurs. By no means the relaxing, on the beach inclusive vacation often found in the Caribbean, it was instead an incredibly educational, eye-opening, and appreciative time spent meeting dozens of wonderful Cubans, observing the venerable and oftentimes crumbling architecture and infrastructure, and quite simply observing first-hand a country few Americans have since the days of Hemingway.

Friday May 6th 

Getting There

At the time of publishing there are no direct flights from America to Cuba except for chartered, pricier flights (commercial flights are expected in fall of 2016).  Instead we opted to fly a red eye to Mexico City using Delta miles, with a connecting flight to Havana.  To travel to Cuba an American has to have their ducks in a row; your visit must qualify under one of 12 US government-approved categories.  When you book flights into Cuba, reserve accommodations, board the flight, etc. you must state which category you fit into.

The Havana airport is comparable to one of the smaller regional airports in the US.  Simple but gets the job done.  The biggest piece of advice here – head straight to the currency exchange on the outside part of the airport, next to the car rental stations. Cash is king (almost all debit/credit cards are not accepted), and everyone arriving in the country had to exchange cash to get a taxi into Havana.  We waited for over an hour in line just to exchange money, and on top of that there is the 10% fee for changing USD, Euro, and British pounds.  The Cuban Convertible Peso (“CUC”) is fixed with a 1:1 ratio on the American dollar, but keep in mind the 10% fee.  Two things we would point out: first, if you can get a taxi to take American dollars for your fare, this could be a better use of your time as there are many places to exchange money in Havana (we also exchanged at the Saratoga Hotel). Second, upon checking into our return flight at the end of the trip we saw a currency exchange near the check-in counter.  You might want to check out that currency exchange counter if the line near arrivals is long.  After finally exchanging our money, we split the 30 minutes taxi ride into Havana with some fellow Americans for $40 CUC total including tip after negotiating with the cabbie.

Cuba | Documentation Required

Definitely have your documents in order for this trip.

Havana | Currency Exchange at Airport

Our first experience of “Cuba time”, waiting over an hour to exchange our money.


We opted for an AirBnB as our place of residence while in Havana, although “homestays” are also a popular way to go.  The apartment we rented was a prime location for exploring Old and Central Havana and was large (two bedrooms) with a full kitchen and great AC.  Bonuses included a balcony overlooking Capitolio Nacional and Fuenta de la India, one of the key roundabouts in the city, which provided for fun car watching and also great Cuban neighbors.  The neighbors welcomed us when we arrived and invited us into their apartment until Juan Carlos, the building manager, arrived to let us into our apartment.  Only one member of the multi-generation family spoke English (Anthony), and Garret could somewhat speak Spanish, but their hospitality made up for any language barrier.  They offered us vodka and coffee while we waited and shared stories of other family who lived in Miami (we later realized this is a fact that many Cubans are proud of and love to share – family in America, especially in Miami).

Havana | AirBnB Bedroom

Clean bedroom + AC over the bed.

Havana | AirBnB Side Porch

Side-patio on the master bedroom.

Havana | AirBnB Balcony

Balcony overlooking Fuenta de la India.

Havana | AirBnB by Fuente de la India

Can you spot Emily standing on our balcony?

Havana | View from AirBnB

We spent part of each night on the balcony, watching the [Cuban] world go by.

Old Havana

After leaving our bags at our apartment we left the building and headed into Old Havana.  Armed with Lonely Planet’s book on Cuba, we walked around wide-eyed as we soaked up the first few streets of Old Havana.  We grabbed a late lunch at a local restaurant, where the manager greeted us after our meal and asked how we liked the restaurant.  When we shared that we were from New York, he grinned and said, “It is true, the American invasion is coming!”  We chuckled and agreed that yes, indeed it is, we are here trying to beat the first wave.

Old Havana was quite shocking, a mix of beauty and disrepair.  The old buildings are beautiful but crumbling, the sidewalks a constant tripping hazard, people all along the streets opening their front doors to sell coffee, bread, or other simple foods/goods out of what appeared to be their living room.  There are no storefronts in the terms that Americans think of them: no signs, advertising, corporate feeling at all, which was refreshing but also a result of private business restrictions in Cuba.  It was while walking through Old Havana and looking in through the doors of homes that we had our first of many reflections on all of the thing Americans have long taken for granted: modern infrastructure, building codes, carpeting, curtains, Wi-Fi, etc.

Havana | Capitolio

The beautiful Capitolio Nacional, based on the US Capital, will once again receive the Cuban Parliament when restoration is complete.

Havana | Exploring Old Havana

Down the streets of Old Havana.

Havana | Streets of Cuba

Small hints of Cuba.

Havana | Old Havana Business

People try to sell numerous items from their doorstep.

Havana | Old Havana

A common site in Old Havana.


Graffiti of Ernesto “Che” Guevara.

Havana | Old Havana - Iglesia y Monasterio de San Francisco de Asís in the Plaza de SanFrancisco de Asís.

Iglesia y Monasterio de San Francisco de Asís in the Plaza de SanFrancisco de Asís.


We knew one evening should be spent at the La Cabaña fortress to witness the 9pm cannon firing. As this takes place across the Canal de Entrada it is not feasible to walk there, but is a quick 5-10 minute drive. The firing includes a reenactment of traditional Cuban soldiers and is an interesting sight. We would recommend arriving early it was very crowded and the reenactment started about a quarter till nine.

We grabbed a late dinner and drinks at the Paris Café, taking in a local band performing in the café. While departing the café we encountered a group of 20-30 young adults huddled together on the street, hunched over their electronics. We had had zero luck finding Wi-Fi during the day (and didn’t have high hopes), so this came as a surprise. After a few minutes of unsuccessful attempts to access, we were approached by a young man with a small bag selling Wi-Fi cards (essentially a prepaid phone card) for $4 CUC an hour. We were skeptical at first, but when he offered to help us connect we decided it was worth the gamble. The card ended up working and we were thankful to finally connect with the rest of the world, letting our families know we were alive and well, and posting our first Instagram of course! The hotspots are found in/around hotels.

Havana | 9pm Cannon Ceremony
La Cabaña cannon-firing ceremony.

Havana | Internet Card

The internet, this year starting to become more available to the Cuban people.

Saturday May 7th

One piece of advice we had read about and were told multiple times was never to buy cigars from people on the street. These cigars will usually rejects from the factory line. Saturday morning, on our walk to find breakfast, one friendly Cuban started talking to us as we examined a map of the city. He offered directions, asked where we were staying, told us Cuba was fine as is and didn’t need capitalism, then proceeded telling us how today was a big day in Havana, the one day of the year Cuban people could sell cigars out of their house. He went on and on about how big of a day this one day a year was and we were here for it. Not that we didn’t believe him, but we weren’t interested in cigars right then and therefore went on our way. A block or two later a woman said hello from behind us and told us she had seen us near the hotel where we were staying. She also started telling us what a big day it was in Havana as it was the one day of the year the Cubans could sell cigars from their homes. We quickly realized we were getting scammed by her and the very friendly Cuban man, had a laugh and told her we were still not interested.

Los Clasicos

One other piece of advice we had read about but truly didn’t hit home until we were in Cuba – there are hundreds, probably thousands, of classic cars in Havana as a result of the embargo. These cars, or los claiscos, serve both as a way to show the tourists around the city and used by Cubans as an ordinary means of getting around. The coupes tended to be used by locals and tourists, convertibles were almost exclusively saved for tourists wanting a ride, either guided or just for fun, around the city. Garret of course loved it, always starting at the cars and as a result constantly being asked if we needed a ride. Not to worry, we patronized plenty of them during our time there.

Havana | Los Clasicos

Convertible row in Parque Central.

Havana | Garret & el Clasico

The cars were in various shapes, some looking ready for a car show.

Havana | Calle de los clasicos

Common site on the streets of Havana.

Havana | Classic Car Row

Attracting crowds, including the double-decker tour bus.

Havana | Purple Clasico

The cars tend to crowd around the hotels and parks.

Havana | Parque de la Central

Need a ride?

Havana | El Clasico Oranje

All metal, all shine.

Havana | All of the colorful classic cars

Different day, more convertibles to choose from.

Old Havana

After breakfast we made our way to the Centro Cultural Antiguos Almacenes de Deposito San José, a large market on the south edge of Old Havana. We ended up stumbling upon an incredibly authentic market. Not only did the market sell tons of fresh fruit and vegetables, but it also sold tons of raw meat. Slabs of chicken, pork, liver, whole pig heads, etc. sitting on cardboard or other makeshift trays, ready to be weighed on a simple, old fashioned scale and taken home for dinner. Walking through the market, and being literally the only tourists, we took picture after picture and received many friendly smiles from the Cuban workers as they laughed at our reactions. It is amazing the regulation (or lack thereof) that you experience in different cultures.

We eventually got to Centro Cultural market but it was not as authentic as we had thought, especially after encountering the first market. There were a large amount of paintings available for sale, and after purchasing a few small ones didn’t stay much longer.

Soon we were hungry for lunch and decided we would enjoy a meal in the open Plaza Vieja. There were two cafes with excellent live music we were trying to decide between when we noticed a café, Don Eduardo Alegre, on the second floor balcony overlooking the plaza. We opted for this and enjoyed sangria, rice and pork, hearing the music waft through the plaza while people wandered by. The meal was slightly pricier (still very cheap by New York standards) but the balcony well worth it. This restaurant also had one of the nicest restrooms we experienced in Havana. By this we mean, most restrooms are not free and also most toilets do not have seats. So finding a free, clean bathroom and a toilet with a seat was quite exciting.

Havana | Fruit Market

Only locals in this market (besides us).

Havana | Meat Market

Step right up!

Havana | Meat market

Not sure how much the pig head costs.

Havana | Old Havana Royals Fan

The Royals, truly World Champs.


Centro Cultural Antiguos Almacenes de Deposito San José.


Lots of art at Centro Cultural.

Havana | Don Eduardo Alegre

Don Eduardo Alegre on the second floor.

Havana | Old Havana - Plaza Vierja

Excellent view of Plaza Vieja from Don Eduardo Alegre.

Museum de Revolution

Our afternoon was spent at the Museum de Revolution, the former Presidential Palace before the revolution in the late 1950s. To get there we walked along the “Prado”, a boulevard similar to Las Ramblas in Barcelona. It was active, with lots of street vendors, children and classic cars zooming by. The museum/former palace was beautiful, while the content of the museum rather simple (and very propagandized as expected). It provided a lot of artifacts and information (most presented in both Spanish and English) about early Cuban history but mostly focusing on the people involved in the revolution. The museum also has an outdoor area which included some planes, jeeps, and most famously the yacht Granma, used by the Castros for the trip from Mexico to Cuba to start the revolution. Remarkably, they barely touch on the Cuban Missile Crisis, seeming to shrug it off as “the so-called October Crisis”.

Havana | Walking Along "Prado"

The shady Prado, between Old Havana and Central Havana.

Havana | Museum of the Revolution

The museum, guarded by a tank Castro himself supposedly used in the Bay of Pigs.

Havana | Museum of the Revolution Bullet Holes

Bullet holes from the revolution on the staircase.

Havana | Museum of the Revolution Dome

Beautiful interior of the dome in the museum/palace.

Havana |Museum of the Revolution

SAM missile and the engine of a U2 spy plane shot down over Cuba.

Old Havana

After the museum we explored more around Old Havana, including the Plaza de Cathedral, the private business Helad’oro for an afternoon snack, and La Bodeguita del Medio, who claims to have first invented the Mojito in the 1940s.


Friendly people and tasty ice cream at Helad’oro.

Havana | Old Havana San Cristóbal de la Habana

San Cristóbal de la Habana.

Havana | Menu in Old Havana

The new private restaurants are springing up all around Old Havana.

Havana | Wooden Bricks in Plaza de Armas

Wooden bricks in the Plaza de Armas to quiet the sounds of horses.

Havana | La Bodeguita del Medio

Disputes of whether or not Hemingway frequented this establishment.

Havana | Mojito's with Hemingway

Where the mojito originated? We may never know, and don’t spend too much time worrying about it.


Research we did before traveling to Havana recommended walking along the Malecon sea drive to soak in the sunset. We did just this and also enjoyed the view of the lighthouse and forts across the channel. By chance we took a break from walking and right then spotted our friends from the airport having dinner at the private restaurant El Presidente.

We also drove the 8km long Malecon several times during our trip and enjoyed viewing both the sea (devoid of any boats, very uncharacteristic for a harbor) as well as the beautiful yet crumbling buildings that line the road.

Havana | Biking up "Prado"

Biking up Prado.

Havana | Macelón Lighthouse

The Castillo del Morro at sunset, opposite the Malecón.

Havana | El Presidente

Fun having a bite to eat with Matt and Newton, our airport taxi buddies!

Havana | Torreón de la Chorrera

Dinner and live music at the very local Torreón de la Chorrera.

Havana | Macelón Sunset in Convertible

A sunset on the Macelón.

When we arrived back to our apartment that night we sat on the balcony and were very excited to see the portable water truck arrive at the building and hook into the building water supply. It was our second day in the city and we were yet to experience running water in the apartment, other than the kitchen sink. This was extremely frustrating until we saw the excitement on the residents’ faces as the water truck replenished the building water supply. We quickly realized how two+ days without a shower was unacceptable to us fortunate Americans, however this was everyday life for the Cubans. Even though the water had arrived, we did not get running water in the apartment for another day.

Sunday May 8th

Playa de Este

We decided to head out of Havana and see some of the countryside for one day of our visit.  The nearby beach region of Playa de Este grabbed our attention because of the beaches and the fact it was less than a 30 minute drive away.  We hailed a ride for $20 CUC for the drive there and were on our way. 

We enjoyed the day in the sun, Garret engaged with some Cuban teenagers in a friendly game of soccer while Emily became best friends with a young girl celebrating her siete cumpleaños. The young girl and her family did not speak English and our Spanish is extremely limited so the friendship blossomed over shared snacks and the girl speaking quickly in Spanish and Emily responding, “lo siento, no entiendo”.

After a few hours we were ready to head back to Havana and found a ride back to our apartment for another $20 CUC. We were in desperate need of a shower at this point and when we arrived home we magically had running water. The quickest and most inconsistent temperature, yet most appreciated showers were quickly enjoyed.

That evening we enjoyed a dinner at Meson de la Flota in Old Havana before venturing to the “chocolate museum” which was more of a dessert restaurant than a museum but it served up delicious chocolate and did have some artifacts to browse through. We enjoyed a night cap at La Familia (fun third floor open air seating) before calling it a night.


On the highway from Havana to Playa de Este.

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The main hotel in the La Playa de Este area we explored.

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Across the bridge to la playa.

Cuba | Playa de Este Futbol

Garret having way too much fun interacting with these Cubans.

Cuba | Playa de Este Coconut and Rum

Fresh Coconut.

Cuba | Playa de Este Futbol

Garret lost possession almost immediately after the picture.

Havana | Scaffolding Greenery

On the fourth or fifth time walking by we finally noticed the vines had grown on the scaffolding.

Havana | Colorful Old Havana

Parts of Old Havana are restored and colorful.

Havana | Dinner at Meson de la Flota

Dinner outside at the private restaurant Meson de la Flota, topped off with a flamenco show.


Someone really enjoyed the chocolate museum.

Havana | Old Havana Entertainment

The solo accordion player, on the streets of Old Havana.

Havana | La Familia

Ended the night at private restaurant La Familia.

Monday May 9th

We started the morning being guided around Havana by Michael, a really interesting Cuban who studied in India, worked in IT previously, and had excellent English. He showed us the variety of architecture styles used throughout the city.  The day was full of stops where we learned about the site’s architecture style and/or the significance to the Cuban people; these included the Christ of Havana statue, Simon Bolivar, Plaza de la Revolucion, and Parque Lenin.

After a full day of absorbing the different architecture, areas, cigars (interesting article on their current status here) and history of Havana, we had dinner on the Malecón watching the sunset over the water. For our final act in Cuba we sat on our balcony once again, one final absorption of this unique country.

Havana | Architectural Tour - Overlooking city

Overlooking Old Havana and the Macelón.

Havana | Architectural Tour - Statue of Jesus Christ

Christ of Havana statue, cleaned up before Pope Francis’ visit in late 2015.

Havana | Architecture Tour - Ave Simón Bolívar

These were given a fresh coat of paint in advance of Pope Francis.

Havana | Architecture Tour - Cuba Colonial

One of the many beautiful but crumbling buildings on Av Simón Bolívar.

Havana | Bacardi

The Bacardi headquarters (before the revolution).

Havana | Architecture Tour - Che

Che proclaiming “Until everlasting victory, always” at the Plaza de la Revolutión.

Havana | Architectural Tour - Monumento a José Martí

Overlooking Plaza de la Revolutión is the Monumento a José Martí.

Havana | Architecture Tour - "You're Doing Fine, Fidel"

Camilo Cienfuegos saying “You’re doing fine, Fidel” at the Plaza de la Revolución.

Havana | Architecture Tour - Parque Almendares

Endless green in the Parque Almendares.

Havana | Havana Super Tour Architecture Tour

Michael, our wonderful architecture guide.

Havana | D'Lirios Dessert

The dessert was on fire.


A Cuban cigar factory, currently undergoing restoration.

Havana | Riding in a Convertible

No one said you can’t stereotypically ride in style.

Havana | U.S. Embassy

Formerly the US Special Interests Building, now once again the US Embassy.

Havana | Opposite of Capitolio

Brightly-faced buildings opposite the Capitolio.

Havana | Ride with Alejandro in convertible

Got a ride from Alejandro, who showed us a vidoe of his CNN interview and pictures of giving Ludacris a ride while he was here filming Fast & Furious.

Havana | Sunset on the Macelón

Final sunset on the Macelón.

Tuesday May 10th

Our flight departed around 6am so the night before we asked a bell hop at the Saratoga Hotel (we made numerous friends with the hotel workers, including Marcelo, a very kind and helping manager) what time they would recommend we leave for the airport and if there would be taxis available that early.  The bell hop recommend leaving at 4am and brought his friend over who was a taxi driver for the hotel, saying he would be glad to take us.  Sure enough when we walked out of our apartment slightly after 4am the taxi was waiting for us.  We would recommend coordinately a taxi ahead of time if you are heading somewhere this early, as the streets are quite dead at 4am.

(De)parting words of advice:

  • Money…Only cash. When you’re out, you’re out!
  • Don’t drink from the tap, bottled water only.
  • Internet cards (~$4/hr)are hard to come by, buy more than one.
  • Budget a little more than you think, it can add up and without as much structure (we got one receipt the whole trip) and the occasional lost in translation (be specific a ride is for total and not per person).
  • A lot of museums and such closed on Mondays.
  • Bring your walking shoes.  We walked over 37 miles during our 5 day trip to Havana and Mexico City.

Havana | Los Clasicos Cuba

Clasico Cuba.

8 thoughts on “Cuba

  1. This is great! Really good info for my upcoming visit in December.
    Do you remember which guided tour you took? Was it the general one or the art deco one?

    1. Hi Ryane, truly sorry we didn’t catch this until January. We did the general Architecture one, it featured some art deco as well. You can’t go wrong either way. I hope you enjoyed it, let us know!

  2. I have enjoyed reading your posts about all of your travels. Cuba was especially interesting and I’ve determined that I need to wait until running water is more prevalent! 🙂

    1. Thanks for reading, we greatly appreciate it! While the running water was definitely a challenge, it was worth getting there now to see how Cuba truly is at the moment. You can always stay at the hotels as another option! Cheers.

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