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How to Navigate Havana, Cuba as an American Citizen

After a year on sabbatical working as an independent consultant, Edyta found a new position with an approaching start date.

PRO TIP: It is highly recommended that someone starting a new job seek out adventure and go on a trip before hunkering down in a new work environment. You will genuinely enjoy this trip without worrying about the work you left behind, and will be happy and fresh for your new job.

So, naturally I started researching cheap flights for a 5 to 7 day trip.  I found flights to Singapore, Columbia, and Peru for under $400. However, each of these destinations seemed to be experiencing monsoon season at the exact same time.  Not really the best scenario for short getaway before starting a new job. Then I stumbled upon a deal to Havana, Cuba. Weather would be in the mid 80’s for our entire stay, and the $303 USD round trip between Buffalo and Havana was a last minute steal.

I didn’t know this at the time of booking, but the reason this round trip from Buffalo to Havana was incredibly cheap was the result of nefarious political trickery. You see, even though we were travelling with Canadian passports, anyone flying from the U.S. to Cuba must purchase a travel visa prior to boarding the plane, which in our case was at our layover in New Jersey. The visa cost $75 USD per person, plus a $20 administration fee that is purchased from an independent contractor at the airport gate in NJ. So the real rate was actually $400 USD.

PRO TIP: When travelling to Cuba on a tourist visa, you need to pick 1 of 12 permitted reasons for entering the country. The easiest to fulfill is the “Support for the Cuban People” reason.  If you choose this option, all you need to do is stay at a Cuban residence, in this instance, by booking your stay through Airbnb.

I booked us on a 3 night, 4 day holiday (just in case we ran into weather on the way back) and we booked it 5 days prior to leaving. Cuba is very limited in terms of hotel rooms, so booking last minute was a little risky. Prior to booking our flight I took a quick peek on Airbnb to check on availability, and there appeared to be a wide range of options still available.

STAY:  Since this was a last minute booking, my Airbnb necessities were more simplified than usual.  I needed a central location for walking, an English speaking host, and a balcony (for cigar smoking and general street gazing). We ended up booking Balcones Gizé – owned and operated by Gizelle and Pedro, a brother and sister team. Their place offered extras for a fee that included transportation to and from the airport, home cooked breakfast from the next door neighbor, and private transportation around the city.

PRO TIP: Take advantage of the breakfast if your host offers-it was the biggest serving for the price during our entire trip. The tourist restaurants around town do not have good breakfast options and they can be overpriced. Our neighbor cooked us the meal and brought it to us.

Pedro was a spectacular host, providing us with many helpful tips and recommendations, including securing me some Cohiba cigars and guiding us through a trip to the beach.

Havana, Cuba
Balcones Gizé-Airbnb-Havana, Cuba
My Airbnb Havana Patio

The apartment is located in the heart of Habana Vieja (Old Havana) right next door to the Plaza de Vieja (Old Square).

THE AIRPORT:  Be forewarned José Martí International Airport can be a little bit harrowing.  Security will search your bag thoroughly- they have a “thing” for metal. I have never seen such a sensitive metal detector anywhere on earth. Once they find an item made of metal they will confiscate it. So, it was during this part of the journey where I said goodbye to my cigar cutter.  I’m surprised they let us keep our wedding rings.

Oddly enough, tampons freaked them out too.  A man searching my bag held one up at me like a weapon and sternly asked “Que es esto?” which thanks to my six years of Spanish in High School and College I understood to mean “What is this?”.  Answering him was going to be a problem for I never learned how to say ”It’s only a tampon“ in Spanish. “Um, hmmm es el tampon, la tampoon, la feminine producto.”  A woman security agent finally intervened – whispered something to him, and I was free.  

Or at least I thought I was free. Little did I realize that security was just phase one of the landing process to Cuba. Once through security you are met by stern faced women wearing stark white old fashioned nurse’s uniforms complete with a nurse’s cap standing behind a giant raised platform scouring the crowd for any signs of illness or infection.  Did I mention that their “dais of judgement“ practically blocked the exit doors to freedom, forcing you to get as close to them as possible before side stepping past them to reach the Caribbean sun.

My advice for carry-on luggage travelers is this:

  1. No metal ever (obvi).
  2. Learn how to say tampon in Spanish.
  3. Hold in all sneezes, coughs and avoid wiping your nose at all cost until you reach the fresh air.

MOJITOS:  After about a 50 minute to an hour drive to Old Havana (those classic cars really can’t drive all that fast), drop off your bags at the Airbnb and walk directly to La Bodeguita Del Medio – a famous tourist destination thanks to the writers and personalities which have patronized it: Salvador Allende, the poet Pablo Neruda, the artist Josignacio and many others. La Bodeguita lays claim to being the birthplace of the Mojito cocktail, prepared in the bar since its opening in 1942, although this claim has been disputed.

La Bodeguita Del Medio – Havana, Cuba
La Bodeguita Del Medio – Havana, Cuba

Regardless, it was the first (and best!) Mojito I had while in Havana. They also sold the cheapest one off cigars I could finds. Pick up a couple, light one up, sit back and enjoy the live music. Watch the dancing crowd spill into the streets as you sip on your sweet rum concoction and puff on your purely Cuban hand rolled tobacco delight.

EATS:  La Taberna del Pescador -Calle San Ignacio, No. 260 e/ Amargura y Lamparilla, Old Habana, Cuba. Open everyday 12:30 p.m. – 00:30 a.m. Average price $8-$14 CUC. Go for the lobster, its only $15 USD and is amazing. To be honest, I pretty much stuck to lobster for dinner every night during my stay. It was readily available to tourists and it was relatively inexpensive and prepared perfectly. This place was our favorite, hands down.

El Cocinero – Calle 26 # 57 e/11 y 13 Vedado La Habana, Cuba
Phone:(+53)58420160,(+53)7 8322355 info@elcocinerocuba.com Open Monday-Sunday 12:00 p.m. to 12:00 a.m. About a 20 minute drive from Old Havana. One of the finest restaurants in Havana sits within an old brick factory. Modern and tasty. Reservations recommended. The restaurant is located next door to a hot sport for young Cubans and tourists alike La Fábrica de Arte Cubano.

E Cocinero – Havana, Cuba

La Fábrica de Arte Cubano – Calle 26, La Habana, Cuba. Open Thursday-Sunday 8:00 p.m.- 3:00 a.m. An art gallery and club, Fábrica’s gallery and stage were established inside of a former cooking oil factory, and has since gained notoriety as one of Havana’s premier nightclubs and art galleries. It is an interesting and eclectic vibe and worth a visit, you may even stumble upon a live performance.

La Fábrica de Arte Cubano – Havana, Cuba

SMOKES:  Cigars are everywhere – which is a blessing and a curse.  If you purchase a cigar and smoke it on the street, you will be bombarded by Cubans trying to sell you more Cohibas by the box.  If you are walking down the street and not smoking a cigar, you will be bombarded by Cubans trying to sell you Cohibas by the box.  Like I said, a blessing and a curse.  You need to formulate your version of “NO” prior to entering the city of cigars.  Don’t worry, they understand no, just be polite and firm.

If you are going to purchase cigars from an individual, I would suggest procuring them from your Airbnb host – they have the best deals and they are seeking a good review so they won’t rip you off. Literally every person on the island knows someone who works in the cigar industry – most will only sell you an entire box. Otherwise, hit up these cigar destinations in Havana Vieja.

Fábrica de Tabaco Partagas – Industria #520 e/ Dragones y Barcelona, Centro Habana, Cuba. No longer a working factory but you can still purchase cigars, rum and gifts in this old and beautiful building. Stop by for a fantastic photo. Open M-F 9:00 a.m.-2:30 p.m. A little overpriced. They also do tours of the factory – Tour Fee $10 (Tickets must be purchased from a hotel; check the bigger hotels).

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Partagas Factory – Havana, Cuba

Modern Partagas Cigar Factory- San Carlos y Penalver, La Habana, Cuba. The working factory moved to this location from the Old Partagas building recently; stop by for a tour. Open Monday-Friday 9:00 a.m.-1:00 p.m Tour Fee $10 (Tickets must be purchased from a hotel; check the bigger hotels.)

Romeo y Julieta/H.Uppman Factory – Padre Varela e/ Desague y Penalver, Centro Habana, Cuba. Open Monday-Friday 9:00 a.m. – 1:00 p.m Yet another place in Central Habana to get your Cuban cigar fix.

THINGS TO DO BY FOOT: Transportation is scarce in Cuba. The buses are free for Cubans, but they are always bursting at the seams. Cars are even more scarce, and shared by multiple families. Renting one can be expensive. They are straight up gas guzzlers without catalytic converters, so be prepared to inhale some fumes on the ride. They are also barely reliable. Bipedal transportation is the way to go in Havana (as are most destinations in the world). Here are some of our suggested stops for your journey to Habana Vieje (Old Havana):

Plaza de Armas, Limited by Obispo, O’Reilly, Cuba & Baratillo, Habana Vieja, Cuba – The city’s oldest plaza is surrounded by restaurants and numerous book stands. Little parquets and fountains line the area.

Plaza de La Catedral, La Habana, Cuba – The last of the main squares to be completed; this is one of the most beautiful. Sit, sip on a café con leche, and people watch. Great place for photos.

Plaza de La Catedral – Havana, Cuba

Palacio de la Artesania Casa Del Habano, Empedrado y San Ignacio, Habana Vieja, Cuba – A glorified gift shop, but surprisingly a great place to enjoy free music, get a cigar smoking lesson, grab a bite to eat, and sip on a cold mojito. While we were meandering we noticed a tour group walk into this courtyard – this is clearly a hidden gem that tour guides bring their groups for the “authentic” Cuban feel. You can buy cigars, coffee, rum and various Cuban souvenirs here (we finally found decent postcards and stamps here). Open Daily 10:00 a.m.-7:00 p.m.

Maximo Gomez Monument, La Habana, Cuba – Situated on the edge of the waters (Straights of Florida/Gulf of Mexico); take in the lovely view as you look north towards Key West.

Maximo Gomez Monument – Havana, Cuba

Museum of the Revolution, Refugio #1 e/ Avenida de las Misiones y Zulueta, Habana Vieja, Cuba – Open Daily 10:00 a.m.-5:00 p.m. The entrance fee is 5 CUC. This is a must see attraction in Old Havana. It is housed in the former Presidential Palace, where all Cuban presidents worked, from Mario García Menocal to Fulgencio Batista. It became the Museum of the Revolution during the years following the Cuban Revolution. There are many pictures and artifacts through the museum chronically the revolution. You can even spot bullet holes in the wall of the former palace, which were made during the attack of the presidential palace in 1957.

Museum of the Revolution – Havana, Cuba

Memorial Granma, La Habana, Cuba – Next door to the Museum of the Revolution, across Colon, you will find an open-air memorial displaying many real life armored vehicles. Here you will also find the boat that Fidel Castro used to transport fighters from Mexico to Cuba during the revolution. (Entrance is part of the Museum of the Revolution entrance fee). Open Daily 10:00 a.m.-5:00 p.m.

Memorial Granma – Havana, Cuba

Sevilla Hotel, 55 Trocadero, La Habana, Cuba – Stop in for a snack or a mojito in the sun filled Spanish style courtyard located right off the hotel lobby, but stay for the live band.  The hotel has a very good exchange rate if you are looking to change money, and they also sell wifi cards. While you are there, ask if they sell tickets to the Cigar Factory tours.

Cuban Cars – Havana-Cuba

Bar Floridita, Obispo, La Habana, Cuba – If you are in need of some shade and something to sip on, dip into Bar Floridita.  One of Hemingway’s favorite hangouts – they are known for their daiquiris and fish. Don’t stay too long as El Capitolio awaits.

Habana Vieja – Old Havana, Cuba

El Capitolio, Prado, e/ San José y Dragones, Habana Vieja, Cuba – El Capitolio, or the National Capitol Building in Havana, Cuba, held the government of Cuba from 1929 until the Cuban Revolution in 1959. The current government of Cuba has been slowly restoring the building to be used once again as the home of Cuba’s National Assembly.

El Capitolio – Havana, Cuba

THE BEACH:  You cannot go to Cuba and not have a beach day. Only a short 20-30 minute drive from Havana, we recommend Playa Tarará. This beach is easily accessible to tourists via a the Transtur, an air-conditioned tourist bus. Pick up the T-3 Bus Route (Bus to Tarará) at Parque Central (across the street from the Capitol). The sign for the bus is located on a pole. You need cash in order to pay for the ticket. It will cost you $10 CUC for a one-day pass that is good for a round-trip to and from Tarará. Ask the tour person on the bus when the last bus of the day leaves and how often they stop at the Tarará drop off.

Get off at the Ciudad Tarará/Playa stop #3. The bus will drop you off directly in front of Casa Club. You can buy an all day eat/drink pass which allows you use of the facilities as well. We opted to pay for a few drinks and snacks at the club. We spent most of our time at an almost entirely secluded beach since it was the off-season.

THE END OF A JOURNEY: I thoroughly enjoyed roaming the streets of Old Havana as music oozed through the cracks of crumbling buildings trapped in a constant state of the past. The people of Cuba will be the thing I remember the most – the country’s officials should see them as their biggest asset – as they are always smiling, singing and dancing; seemingly ready to party at a moments notice. Our brief but enjoyable time in this tropical island fraught with memories of a revolution long past with the ever-present knowing of an inevitable high-tech future on the horizon was memorable and lasting. I would go back to Cuba in a heartbeat for the cigars, the beach, and el béisbol, the only thing I regret not witnessing on our trip to the past. I overheard an American calling home on his cellphone in the airport as we were getting ready to catch our plane. The excitement in his voice as he described the crowd at the game made me green with envy.


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