Girl Meets Cuba For The First Time

On top of a roof overlooking Central Havana and the Malecón

Like many Americans, Cuba has long been on my bucket list before I even knew I had a bucket list. A once forbidden territory is now an open field. Below I will share some details of my trip and an overall thought of it.

I split the details of my experience and a tips list into 2 different pieces to make it easier on the eyes.

When our wheels touched down in the José Martí airport…there were a lot of emotions going around the cabin. For some, this will be their first time seeing their families in decades. For others, it was the excitement of setting foot in a once forbidden territory. This flight was the most exciting flight I’ve ever been on. The entire duration of the flight felt like a party. There was constant movement and chatter in the cabins. Some were drinking; some were dancing. That’s how I met some of the people I shared my trip with! A unique flight experience all in all — there was a collective energy of love and excitement that spread throughout the plane.

There were even some celebrities sitting up in first class. I’d like to think that Cuba is a great spot for any famous person to visit right now. For the most part, you won’t see many Cubans whipping out their phones to take photos or videos of world celebrities walking down the street. From my observation, they might not even be recognizable to the average Cuban.


Havana is split up into 3 neighborhoods: Vedado, Central Havana, Old Havana. Each neighborhood has its own rich history and I encourage you to stop and befriend a local that may give you more insight into each area. I stood in awe — admiring all of the dilapidated buildings I walked past in Havana and thinking about how much this city has gone through and continues to go through. Remnants of the 1990s (began in 1989) economic crisis can still be seen in the streets and buildings of Havana. I dedicated a day to explore each neighborhood.


Vedado is the old neighborhood of the upper class; pre-revolution. It’s less touristy with more of a local vibe. Anyone elderly who is still living in these homes used to be the elite — now, not so much. Yet, they have seen so much in their own country…from Fidel’s rise to power, the special period of Cuba, to then President Obama rolling through the streets of Havana. In a way, they are history.

Things I’d recommend visiting in Vedado:

  • Hotel Nacional de Cuba
  • Plaza de la Revolución
  • Fábrica de Arte Cubano
  • U.S. Embassy

Hotel Nacional de Cuba carries a lot of culture and history within it. It has a classic charm with a beautiful oceanfront view. Just walk through the lobby to get to the back garden. If you go further out you’ll be rewarded with an expansive view of the ocean — the street and the Malecón just a few feet away from you.

There are 2 preserved cannons from the Santa Clara Battery and a couple of bunker entrances of the 1962 Cuban Missile Crisis. Just imagine how it must have felt to be looking out to the ocean from there…as armed ships come towards you. Those cannons were built to defend this island once upon a time. I imagined Fidel Castro and his team conspiring down in those bunkers. This is definitely a place worth visiting. Don’t forget to bring in a bottle of rum and a cigar to fully enjoy the views and appreciate its history from one of the benches!

A bunker entrance and the Malecón behind me


The Plaza de Revolución played a significant role in Cuban history as it has hosted many political rallies and is the stage for many of Fidel Castro’s address to the Cuban people.


Fábrica de Arte Cubano was very cool! I’ve never visited anything like it. It’s a huge building with many levels to get lost in. From art to music to booze — you won’t be bored! I was surprised by the space. I’d be in one room and would feel completely isolated from the other levels. You’d forget that there were other attachments! Each level has its own purpose and theme and can stand alone by itself. And just when you think you covered all bases…you’ll be welcomed with a new room at the turn of a corner!

A piece of art in Fábrica de Arte Cubano

As you can imagine, this place gets packed on the weekends with a mix of locals and tourists. Very diverse. There’s a cover of 2 CUC per person to enter. You’ll be given a booze card once inside and that is your ticket to the alcohol. There is no cash handling inside except for at the entrance. You’ll get a stamp on your card every time you order something and it gets tallied at the entrance once you’re ready to leave. You will need that card to exit FAC; with or without stamps. If you lose your card then it is a flat 30 CUC fee to pay as you exit. They’ll check your bags for any sneaked-in alcohol! Although I was able to get a beer in by sheer luck ^.^

Try to arrive by 9PM to beat the line. Even with a queue it’ll move pretty quickly.


The US Embassy in Havana is especially significant as it holds many historical and cultural implications. It is definitely worth a trip to check out even if you don’t plan on going inside or couldn’t get an appointment for a briefing. Stand in front of the Embassy and soak it all in. Imagine all that it has gone through in history: U.S. diplomatic mission pre-revolution, the lowering of the U.S. flag in 1961, to creating the Interests Sections Agreement and having Switzerland represent us in the embassy, to reestablishing diplomatic relations in 2015 and raising our flag once again after 54 years. It really is quite amazing. There is a photo hanging inside the embassy lobby, alongside a copy of the constitution, that shows the three Marines (Larry C. Morris, Mike East, and Jim Tracy) lowering the American flag. I never felt more patriotic.

Fun fact: the same Marines presented the flag to be raised by the Marines assigned to the post in 2015.

The 1 hour briefing in the embassy is very informative and I highly recommend anyone visiting Havana to make an appointment. Cuba is changing rapidly. A good example of this is how the restrictions for U.S. citizens visiting in January 2017 has changed in April 2017 — a mere 4 months. Things move quickly in the background. It’s becoming more and more lax to travel to Cuba as an American citizen — but there are still requirements to meet!

There are 3 goals that Cuba is trying to achieve all at once: holding a single party government, economic growth, and economic equality. Our presenter personally believes that their goals are ambitious and will not work. He used China as an example — they achieved the first 2 but still have an enormous gap between the rich and the poor.

You can inquire about the 1 hour briefing by emailing

Unfortunately, I wasn’t able to fully explore Vedado because of time and the weather. The day we dedicated to Vedado was full of intense rain — I’m talking cats and dogs! We thought it was a good idea to explore Vedado before heading to dinner and FAC. Yes, even in pouring rain. In the name of adventure and “we’re in Cuba so fuck it” spirit, we trotted through knee deep puddles and (at least I did) welcomed a pouring shower onto my clothes.

The broken and unmaintained infrastructure of Havana resulted in a poor irrigation system that left blocks completely flooded. We couldn’t even see the sidewalk at some points and had to traverse murky water to get to the only piece of land we could see: the middle of the road. It was definitely a little sketchy walking in water that deep as you don’t know what you could be stepping in. Some of the sidewalks are uneven and broken that you could be stepping into a hole and risk twisting your ankle — something that would’ve definitely happened to me. But don’t worry, if you get hurt in Cuba you’ll have travel insurance (mandatory) and healthcare is free in the country!

The city’s infrastructure wasn’t the only thing that was shoddy — my rain gear was too! Monique and I were prepared with our rain shells and plastic ponchos (she more so than me with her Teva sandals and dress while I wore jeans and sneakers thinking how bad could it be…) but due to perhaps a poor poncho design and a more likely user error, water leaked in from the neck of my poncho and inside to my zipped up rain shell. Don’t ask me how this happened. I still can’t figure it out. I was 90% soaked when we arrived to dinner. However, I had a lot of fun walking in the rain! It wasn’t hot rain either — quite cool actually. Cool enough for me to wear pants and sneakers.

Why me


You’ll learn very quickly that Havana is a super walkable city. We barely used a cab to get around. Your chevro-legs are the best mode of transportation to truly get a feel of Havana! Central Havana is a gem and our casa particular was right in the middle of it. I had loads of fun navigating through the alleyways of our quaint little neighborhood! The Malecón was in front of our casa and I welcomed the ocean breeze through our windows every morning. Make sure to find the Callejon de Hamel alleyway! It’s an iconic street full of interesting street art and showcases a pure Afro-Cuban culture.

Dilapidated buildings in Central Havana


This the spot most tourists flock to — and with good reason! It is the city-center and embodies all of Havana’s history; new and old. A significant landmark to visit and a great place to get lost in as everything is close to one another.

There are a lot of things you could visit in Old Havana. Here a few to start your day:

  • Museo Nacional de Bellas Artes de La Habana (think MoMa)
  • Museo de la Revolución (across from Bellas Artes — be ready to be blown with propaganda)
  • Plaza de Armas (once a place for refuge in case of an attack on the city is now a book fair during the day)
  • Plaza de la Catedral
  • El Capitolio (resembles the Capital building in D.C. — check out this area at night!)
  • Hotel Ambos Mundos (grab a drink and relax on this rooftop bar/check out room 511 where Hemingway stayed)
It’s lit


“Havana is the capital of Cuba and the largest city on the island. It can be hot and humid; dirty and broken. It is a mix of old and new; ugly and beautiful. It is a perfect canvas to showcase a fascinating and unpretentious culture, in a vibrant, historic atmosphere.” — Mario Rizzi

Whether or not you choose to visit the things above, the best advice I can give you is to literally get lost in the city. Admire it. Breathe it. Embrace it. There are hidden charms all around the city if you are willing to stop and let it captivate you.


I highly recommend visiting Viñales, a countryside town west of Havana. It’s only a 2.5 hour drive, totally doable! I liked this town better than Havana; only because I have a great love and passion for the outdoors. One day was not enough for me and I shall be back for a one week stay!

Lunch at El Paraiso farm — Ernesto to the right!

Forget about booking a tour company. Ask your host/hotel to reserve a private driver/guide for your party. It should be much cheaper and you can reserve the day before. I have the contact of my driver Ernesto, who was such a sweet man and made sure we did everything we wanted, but he only speaks Spanish. Make sure your host/hotel communicates clearly to Ernesto what your itinerary is if you don’t have any Spanish speakers in your party. Downloading the Spanish offline language from Google translate can help as well as having your itinerary printed out in Spanish. Below is a list of things I did and Ernesto has already traded contacts with these establishments for future trips. You should be set with him if you decide to go with this itinerary! You don’t have to do all of it as well but if you do, plan to leave at 7am sharp.

  • Ernestos cell: +53 5 475–7252. He has an emerald green Chrysler ’54 that can seat 6, including himself
  • Los Jazmines lookout of Viñales Valley
  • Lunch at El Paraiso (make sure to make reservations in advance!!) — a beautiful organic farm with a breathtaking view of the Valley. There are 2 places with the same name — make sure you get the right one!
  • Tour of a tobacco farm
  • Tour of a tobacco sorting house
  • A 1, 2, or 3 hour horseback riding tour of the Valley
  • A 1–2 hour walking tour of another section of the Valley
  • Rock climbing: contact! This definitely made my trip. The area we climbed in was so beautiful and amazing. There are only 5 certified rock climbing instructors in Cuba — Yandry is one of them and will take good care of you! 
    Note* If you are a climber and have some gear you don’t mind parting with…please bring it and donate it to Yandry and their rock climbing circle. This is how any rock climber in Cuba gets their gear. We are a community that takes care of one another~ All items that are donated are put in a communal pile for all the instructors to share. As you can imagine, quality gear is not prevalent in the country. Everything they have was donated by foreigners. They are in need of ropes and bolts.
Yandry the man!
Walking towards the limestone walls to climb!

It isn’t news that Cuba is undergoing a rapid change as the U.S. continues to work on improving relations with their island neighbor.

Cuba is currently going through 4 transitions: economic, political, generational, and technological. I was happy to hear that the LGBQT community is alive and running with growing support as well. I was wondering if such a community existed as I observed and people watched.

“Mommy, what will the black man want?”

The economy is growing as tourism sees an all-time high; but not growing fast enough for its people. You will still find a hustler on every block trying to find a way to supplement their income. Change may be moving in the background but daily life in Cuba is still very much slow and unaltered.

The generation that will replace the people of Castro’s era are developing a new ideology. I don’t think it’s a surprise that this age group consists of people in their 20s and 30s. I wasn’t sure if I should label them as the millennial generation as a millennials characteristics vary by region, social and economic conditions and is mostly referred to in western countries. But one thing is for sure — they’re thinking outside their box.

Don’t get it twisted — they think it’s great that the older folks fought in the revolution for the better of their country. But now they’re asking,”what has this really done for me now, in the present?” They haven’t grown up as personally invested in the revolution. They grew up in a society that is always taking one step forward and two steps back. I found it very interesting that the revolution was fought and won by the ideals of the youth, to now having it questioned by the youth of today. The country was built on the dreams of young people and, ironically, is now discouraging the dreams of its young people.

I think this sheds light on how powerful the force of a generational mindset can be…no matter where you live. Cuba’s youth is able to share similar cultural experiences with the rest of the world despite the fact that Cuba has not been modernized or westernized. I think this is a highly significant factor given its history. For the most part, everyone is completely unplugged from the modern world yet still able to adopt cultural trends that has influenced their thought process and opened their think tanks. So really, they’re not that unplugged and is still in the loop with trends like Adidas, Drake, Nicki Minaj, The Weeknd, and many more artists and brands.

I befriended a gentlemen who shared with me that he wanted to open up his own business — an agency or gym of the sort. But he knew he could never really call it his own (he didn’t explicitly say it like that though). “His” business would’ve been heavily regulated and would have to follow strict state rules. Everything in Cuba is shared and communal; the country always comes first. So how do you become your own person and make something out of yourself when you were raised in a state that was all about itself? Where do you draw the line between you and your country? Individualism is uncommon in a communist society. But I think that questioning your world is the first step in building towards that. I told him one of the best advices I ever got from a college professor was to question everything; even his class.

A promise of the revolution was free and equal access to health, education, housing, food, and so on. The country will take care of its people and in return, asks for the same. They will take care of you as long as you believe in their revolutionary ideals. There is no room for the individual. Whereas, in the U.S., the individual is celebrated and promoted. But we don’t have the perks that Cuba has: free education, health, food, housing, etc. What an interesting dichotomy.

There’s also no incentive to work hard as you are limited to state jobs — further discouraging the dreams and drive of the Cuban people. I always assumed that people my age, no matter where they lived, had an innate drive to work hard towards their dreams, goals, and passions. I felt that this was a universally collective thought that has been pushed within my generation.

An alternative to working for the state is in the private sector. You can operate your own business in the private sector but it is technically still controlled by the state. And either way, everyone makes the same amount of money. It doesn’t matter if you worked 80 hours a week — you will get taxed higher to get the same payout as the person working 40 hours a week (sounds familiar?). That is why there is a “black market” for supplemental income. This is why you see hustlers on every corner in Havana.

It’s common to see branded items sold for a cheap price on the streets. Although, you don’t really know if they’re real or not. Where did those items come from, you ask? It was probably a part of an inventory that “got lost.” Our embassy presenter said it’s common to see a “potato that fell off the cart” situation in the black market. The man who pushes a cart of potatoes for a living could have “lost” some while transporting them. Then, voila! You see those organic potatoes sold on the streets. I’ve had hotel employees come up to us and try to sell us boxes of cigars for a cheaper price — as we are standing in front of the cigar shop of their hotel! This is the black market. This is their grind.

Overall, I had such a great time in Cuba and learned a great deal about its history and culture that got the gears in my head turning. I find the U.S.-Cuba relations fascinating as change is unfolding right before my eyes. We are all a part of history and I encourage you to take advantage of that! I’m really intrigued to see how the path Cuba will forge itself in the coming years will develop into.

Note: Please don’t go around asking locals what they think of their government or state. Be very careful on how you bring these topics up, if you ever do. Remember, Cuba is still very much a Marxist-Leninist one-party republic. We can leave Cuba but Cubans can’t. Be sensitive to this topic and realize that Cubans free access to the U.S. (wet feet, dry feet) is gone. I was fortunate enough to have built a relationship with someone and slowly introduced the topic after feeling his personality out and vice versa. And most of the information I talked about above are formed thoughts as a result of the U.S. Embassy briefing .