Solo Female Travel through Cuba for 7 Days

Four days before my flight, I found myself with an unplanned solo female trip to Cuba. This was the first time I traveled all alone to a politically controversial and developing country which most Americans had very little knowledge of. I was one of the first Americans to go in 2015 after President Obama loosened the Cuban travel restrictions. Scared and excited, I was finally fulfilling my dream of visiting Cuba. With only my first night’s accommodation reserved, I boarded a plane to Havana…


El Malecon de la Habana Sunset
El Malecon de la Habana – Sunset

The elevator opened up to a locked door which began to beep urgently like a time-ticking bomb. I frantically rang the doorbell for someone to open up. Was the elevator going to drop to the ground? Eject me out? The door was finally opened by a Spanish-speaking man who seemed very distracted by more important matters than my presence. He barely met my gaze as he let go of the door and sauntered away. I wheeled my luggage into the living room of Casavana, where a rowdy and intimidating group of Spanish speaking individuals surrounded a luxurious glass dinner table. Were they the family that lives at this casa particular (typical Cuban homestay)?

Related: How to Travel to Cuba, Legally

The casa’s innkeeper, Emil, a blonde haired and blue-eyed Cuban who looked disoriented by the ruckus, gestured me in. As he guided me to my room, in his broken English, he offered me a welcome mojito and gestured me to sit down with him about any questions I might have.

A couple from Switzerland joined our table discussion. Emil enthusiastically suggested La Fabrica de Arte Cubano (FAC) as a night time excursion. Feeling internet-less, disconnected, and solo, I gushed that we should all go together. But the Swiss were jet-lagged and Emil had to finish his shift. Feeling sympathetic that I was a woman traveling alone, like most other Cuban men I would meet, he counter-offered to show me Havana the next day.

Currency Exchange Booths (Cadecas)

With my accommodation settled for the night, I made my way to the Hotel Presidente  a few blocks away to exchange Mexican pesos I’d converted in Cancun for Cuban currency. I was stopped in my tracks when the cashier told me she could not accept the Mexican pesos. Euros or Canadian money only she winced sympathetically. To make matters more difficult, it was Sunday and all the nearby cadecas (exchange houses) were closed. I took the 13% hit and relinquished some USD to keep me afloat until the next day.

My stomach grumbled. I clutched onto my newly exchanged Cuban bills as I hiked up to El Ilidio. I peered around the restaurant for a good spot to eat and read but instead found the Swiss couple waving me over like parents who’d found their lost child. After stuffing myself with every sea creature imaginable, I refused to go home with just me, myself and my mind, wide awake at 8:30 PM in Havana. That’s when I remembered Emil’s zealous encouragement to check out La Fabrica de Arte Cubano (La FAC).

Havana Nightlife – La Fabrica de Arte Cubano (FAC)

fabrica-de-arte-cubano at night

The cab dropped me off in front of what looked like an abandoned factory. I wasn’t sure if I’d made the right decision to venture out to this place alone. But as soon as I stepped foot inside La FAC, I realized it was one of the most awe-inspiring places I’d ever been to in the world for nightlife.

La FAC is a maze of 3+ floors with live theater, live music, multiple bars, food stands, dance floors, incredible art exhibitions, an outdoor terrace, and more, all simultaneously taking place throughout the building. I spent the night there seeing, doing, tasting, and absorbing all of it. The ecclectic visiual arts and intellectual stimulation through the performances was enchanting.


Streets of Vedado

In the scorching sun, I hiked uphill to the nearest Cadeca to exchange my Mexican pesos. It was particularly hard to stay tranquil and cool with the constant street harassment from men at every corner. I guess machismo wasn’t on the revolution’s agenda, I thought grimly.

Avenida 23 was crowded with long lines of Cubans and tourists waiting to reach the Cadeca and/or bank. After an hour of standing in a real life sauna, the teller asks for my passport which was back at Casavana. I swung around in despair, still holding on to a million pesos. It was almost noon, and I had yet to eat or explore much of the highly coveted Havana. I cursed the world as I waved down a collectivo taxi.

The security guards of the Casavana sweetly advised me: “Don’t worry dear, you will resolve this”. The typical Cuban perspective on life. To “resolver.” But it oddly calmed me. Trying to recompose myself from melting, I bumped into Emil. As we moved my luggage into their neighbor’s home who had space to accommodate, he explained he is a web developer and had some questions about a business project he was setting up in the tourism sector. I invited him to tell me all about it during my hike back to the Cadeca for a fourth attempt at exchanging pesos.

El Vedado Avenida Presidente
El Vedado, La Habana, Cuba – Avenida Presidente aka Calle G

My skin sizzled in the sun as I tried adapting to my new environment while paying attention to Emil, who seemed to get better looking as I was turning into a crimson burnt puddle of skin and sweat. Finally, we got to the Cadeca with no line! The day was brightening up and since I was walking with a man, I wasn’t getting street harassed anymore.

I swung the Cadeca door open but was halted by someone standing in the dark entrance. The electricity was out. They were closing down for the day.

As we hiked up to the next CadecaI could feel my face burning from the intense heat. But half an hour later, I came out triumphantly holding a thick wad of Cuban currency. Finally. Things in Cuba work very slowly, I began to realize.

We sat down outside where I tried to pry some political perspective out of Emil but like most young Cubans, he sternly expressed his apathy for politics so I dropped the subject.

We parted ways at the elevator but before heading upstairs he boastfully chirped: “I’d like to invite you somewhere, I don’t know where yet but I’ll think about it.”

Central Havana and Old Havana

My first visit to a privately-owned (aka not owned by the government) Cuban restaurant was the famous La Guarida. It’s an almost overly hyped-up restaurant in Havana where celebrities such as Conan O’Brien and Beyonce have visited.

Afterwards, I hopped into a cab, and by cab I mean someone’s car with a driver loitering outside the restaurant, and took off to the Old Havana. I began to do this often, at first cautiously but by the end of the trip, completely comfortably. It’s the way to get around in Cuba, and it felt incredibly safe. “Aquí hay control,” my airport cabbie confidently said to me my first day. Here, there is control.

I got out at the Plaza Cathedral and sauntered past several crumbling old buildings which reminded me of Sicily. Unkept and decaying. As it began to pour I hopped into one of the many bicitaxis.

I visited an artisanal market called Almacenes San Jose which was OK, a lot of the products seemed mass produced and unoriginal. The bicitaxi driver asked about my life, with some casual flirting as would happen from nearly every Cuban man.

Booking a Tour to Vinales

Touring Havana by foot

In the quest to find a tour to Vinales, I ended up accidentally touring a lot of Havana by foot. The search eventually led me to the Capitolio building in a touristy but gorgeous area. I ate, drank, wandered and gazed at the beautiful 50’s cars.

After booking a $60 trip to Vinales with Cubacan (located in a Hotel Inglaterra), I wandered some more and accidentally bumped into the historic La Floridita! Hemingway’s bar. It was bustling with salsa and adorned with all sorts of homages to Hemingway. I ordered his famous daiquiri and listened to the live salsa as I munched on plantain chips. I wanted to purr with merriment like a satisfied cat. After over a decade of yearning to touch Cuba, I was finally here; absorbing the country, it’s history and music. I was excited for how much more there was left to see and do. And excited to be getting a first-hand look at some of the people and their way of living.

Local Havana Nightlife – Submarino Amarillo 

Submarino Amarillo Habana Havana NightlifeSubmarino AmarilloSubmarino Amarillo

Beatlemania is still very much alive in Cuba. Submarino Amarillo was a sweet spot for listening to live Latin rock music played by young Cuban bands. I don’t believe I saw another tourist here but there were two cover charges. Tourist and Local. Walking in with Emil, I passed for a local and paid the smaller fee!


Guayabita Factory Tour – Viñales, Cuba

Guayabita Factory in Vinales Cuba

It was not a long drive to Viñales, maybe two hours. The crowded group tour of a factory that produced a liquor called guayabita felt pretty rushed. The employees barely looked at us as they worked away in unison. I contemplated walking away to see the town and take photos but I got as far as half a block north and the street harassment from men was unbearable and kind of intimidating so I turned back around.


Tobacco Farm – Vinales, Cuba

Our next stop was a tobacco farm where we huddled into a barn together to learn about tobacco production. I found it too cluttered inside, so I wandered around the farm. It was a beautiful, bright sunny day. Everything from the grass, to the quaint mountainous background, glistened in sun-toasted pale green hues. I bought a cigar for $1 that I would later find out was the crappiest cigar in the world, worth 1 cent in Cuba. Whoops.

El Mural de la Prehistoria, Vinales, Cuba


Towards the end of our tour, we ate at one of the tastiest restaurants in Cuba, overlooking a small mountain with dinosaur murals. I never knew the name of the restaurant, as I was too distracted at the sight of the first American I’d seen in days. He was a beautiful, bright baby-blue eyed fluent Spanish speaker living in Colombia. Cuba seemed to attract travelers of amazing caliber. Travelers interested in culture and history. I was elated to share our Cuban adventure stories in the alleged presence of dinosaur bones, delicious food, and live music.

Caves & Mogotes – Vinales, Cuba

Mogotes de Vinales Cuba
Mogotes de Vinales Cuba

The next excursion was also rushed. We rode on a canoe ride through dark caves.

Lastly, before heading back to Havana, we stopped at a lookout point to see mountains (mogotes). Again it was not a bad sight, but it felt all felt rushed.

Vinales, we will meet again someday. Properly.

Rainy Night Alone in Havana

I returned to Havana during a downpour of rain. I trudged through two feet of flood back to my new casa and found the owner anxiously holding onto his TV remote. “I’ve been waiting for you” he turned to me, eerily.

Oops. I’d forgotten to pay him and I was leaving the next morning. After handing him some cash, he informed there were no other guests or innkeepers in this enormous 9 bedroom apartment and then left. Just me, sleeping there alone during a storm. I checked my phone, no internet. No roaming. Just a large house with lots of doors and empty bedrooms that made loud creaking sounds. In bed, I began to wonder if I could get robbed or hurt by some Cuban criminal mafia-like group that targets lone travelers.

Cuba was safer than anywhere else I’ve been in the world. But it was still a foreign country I was not fully familiar with and there was NO way to communicate with anyone in the case of an emergency.

It was a completely new and unfamiliar feeling of isolation and disconnection from the world. I’d never felt this before in my entire life. I’d been gifted with an absolutely foreign sensation and I wanted to give it back. With the intense downpour outside, there was nowhere to go. Ironically, I fell asleep listening to The Martian, an audiobook about a man stranded alone on Mars.


I’d never woken up so grateful to see the morning sun in full sight. I was relieved to hear city noises through my closed window. Havana was back up and running again with people to see and places to be! I excitedly packed my bags and got ready. As I swung my bedroom door open, I was halted in my steps by a hot, stifling gust of humidity. I saw the casa owner on the balcony hanging clothes to dry with his shirt pulled above his panza (big belly). This is common in Cuba, shirtless men with their panzas hanging out in public. It would get so hot at times that, I too, often wished I could let my little panza out to breathe.

He drove me in his 1970’s, Russian-made hatchback. A luxury in Cuba, easily worth about $15,000+ USD there. I subtly searched for a seat belt, in case there wasn’t one it wouldn’t be an insulting expectation, and there wasn’t. I’d soon learn to stop searching for seat belts in Cuba.

Negotiating a ride from Havana to Trinidad

I cracked my knuckles and stretched my neck as we pulled up to the bus station. Game time. We approached the group of guys offering long distance car rides. One said he would drive me for $50 to Trinidad.  That’s how I knew my target price was at most $25. I countered his rate, by pointing out that the Viazul bus was $25. He countered by pointing out that Viazul could take twice the time. I countered by offering to find other travelers so he’d make more and I’d pay less. We agreed.

Feeling like a racist, I searched around for gringo-looking folks and found a blonde-haired girl with a giant backpack. Bingo. She was going to Cienfuegos, 1 hour from Trinidad. Double bingo. Another dude (#2) approached, “I’ll take you and her for $30 each!” I went back to see if the guy #1 would do it for less, he said $25 each. I went back to give the good news to Catalan girl but just then the other guy ran behind me saying “Ok $25! And I’m licensed, and I have AC!” Then a crowd began to form, including my casa owner who advised that I go with guy #2 who’s from Trinidad, while others said it is honorable to go with the #1. “We want to leave now!” demanded the feisty Catalan girl with a piece of jewelry on her front tooth. The Trinidad local obliged.

We sped off to Trinidad in a car without an odometer. I can only assume we were going over 100 miles per hour based on the deafening winds blowing into the car. A fabulous four-hour drive. And since cars are a luxury in Cuba, the roads were nearly empty.

Discovering Trinidad

Famished and sweaty, I quickly dropped my things off at my Airbnb. I rushed into the nearest restaurant where the waiter took my massive order. I waited 45 minutes for my food, before finally asking him “How much longer?” and he responded “How much longer for what? Did you order something?” Damnit, Cuba!

I could feel myself getting skinnier as I stormed out and hiked over to La Ceiba‘s.  The food here came quickly and the rooftop view was gorgeous, but I found myself constantly fighting off dozens of flies.

Trinidad–one of my favorite cities in the world–is a historical, colorful, musical, and magical cobble-stoned city… engulfed in flies.

La Ceiba - Trinidad - Cuba - Lobster - Sea Roach!

Balancing/hiking over the cobblestones, I found a beautiful park with wifi in front of the Iberostar Grand Hotel. That’s when I saw an email from Emil asking to meet up before I left. My time was too limited to plan anything for Havana, so I welcomed him to join me in Trinidad and logged off.

I found a tavern called Taberna La Canchanchara. It was here I discovered what is now my favorite cocktail in the world: La Canchanchara. Three simple ingredients: rum, lime, club soda, and honey at the bottom with a wooden stirrer. It was fresh.

La Canchanchara - Trinidad, Cuba

Nightlife in Trinidad

Still a little nervous about going out by myself at night in a foreign country, I braved my anxiety, got dressed and hobbled up and over the cobblestones to La Botija. It had great prices and nice music, but I got there too late to find a seat

Next, I tried La Trova only to find a far much older crowd and still no empty seats.

Finally, I settled at La Casa de Musica perched at the top of some dark steps and ordered a beer. It became one of the most memorable nights of my solo time in Cuba. Admiring the gorgeous night scene of Trinidad from above the top of the steps, I swayed to the music. Below the steps, I saw a couple of brave souls showing off their salsa skills next to the stage. As I scanned the steps, I noticed several solo travelers just like me. I did not feel alone. I felt buoyant.

Casa de Musica Trinidad Cuba Nightlife
Casa de Musica Trinidad, Cuba – Amazing Nightlife

I noticed the occasional jinetero (Cuban guy or girl who looks for tourists to date), one of which I had to angrily shoo away. It became increasingly crowded as more tourists and locals alike began to fill the steps. Two women (Shirley and Janice) sat next to me. They were both traveling solo but met recently in Cuba. Another solo traveler (Daniel) from Israel introduced himself along with his friend (Bernardo), the jinetero I angrily waved away earlier. Bernardo and Daniel tried to show me salsa in a futile but much-appreciated attempt.

After getting a huge pizza pie folded into plastic bags, we all agreed to meet up the next day for a trip to the beach.

DAY 5 – Trinidad

I read an email response from Emil saying he’d be happy to join me in Trinidad. I’d been in Cuba for less than 4 days and was making friends both locally and internationally. Is this was traveling solo was always like?

Around Trinidad: Nature, hikes, waterfalls

At the main plaza, all I had to do was make eye contact with a Cuban man and he would offer me a taxi ride. I whimsically asked to be taken to a waterfall with horses (there are many such as the beautiful Topes de Collantes). The taxi driver drove me to Parque El Cubano. There were no horses here, but he said the waterfall was about 20 minutes away.

The hiking trail was completely empty. It was so quiet I could hear a dog barking at an ambiguous distance followed suddenly by a rattle in the bushes. I picked up a rock and swung around wide-eyed. What happens if a snake bit me and I had no way of calling for help without a phone? I stomped back to the entrance.

In some exaggerated distress, the type that usually only a woman can pull off (a gift and a curse), I demanded better directions or someone to come with me. Just then, a group of Americans on a people-to-people tour were entering the park. The ticket booth representative waved me off and told me to join them, and I shamelessly tagged along.

Everyone on this tour was a solo traveler with an interesting story. “While he was being trained to point a gun at me from Havana, I was being trained to point a gun at him from Florida,” recounted a 60-something-year-old of his conversations with an ex-military Cuban.

Ninety minutes later, we finally reached the waterfall. It was tiresome but well worth it. A gorgeous natural swimming pool led to a waterfall with a cave behind it. It was paradise.


Playa Ancon

I got back to the city center just in time to meet everyone (Cuban, Isreali, British, and Bolivian friends from the night before) for our beach excursion. Playa Ancon reminded me of baby blue cotton candy. It became another memorable part of my trip.

For $4 I got a plate of fresh fish, rice, and lettuce with a priceless view.  We were picked up and dropped off in a beautiful 1950’s car. I wandered back to my casa particular and just as I was getting lost, I bumped into Emil. Was Cuba the Matrix? How was everything working out so well?

Nightlife in Trinidad

At night, we all met up at Taberna La Botija, where I bumped into the Swiss couple from Havana! Yep, Cuba was the Matrix. Then our new Brazilian friend from the Playa Ancon and his roommate joined us, too. Our table began to grow bigger and bigger. I arrived in Cuba alone, and four days later I was in the company of fascinating people from all over the world: Cuba, Bolivia, India, Brazil, Poland, Switzerland, and England.

La Botija - Cigars - Cuban - Trinidad - Cuba

At the end of the night, we ventured off to find La Cueva– an underground club in a cave so hot that even the limestone was sweating.

DAY 6 – Trinidad & La Lisa

Savoring the Last Bits of Trinidad


I felt more and more relaxed the longer I stayed in Cuba, especially on this gray and cloudy day. The Iglesia and Convento de San Francisco (pictured above) is a church museum that turned out to have one of the best views of Trinidad.

From Trinidad to the Local Outskirts of Havana

At the train station, I engaged in the usual haggling for a ride. This time, I slept for most of the drive, occasionally waking up whenever the rainfall became particularly loud.

We arrived at Emil’s hometown of La Lisa late at night. La Lisa reminded me of a barrio in Santo Domingo, but calmer, safer and without the tigueraje. I was grateful to experience a snippet of how Cubans in the outskirts of Havana lived:

  • The water only arrived on certain days, so there were large bottles and tanks of water stored throughout the house and its backyard.
  • Just like DR, sometimes the electricity would come and go.
  • There were roaches so big, I could actually hear them as they crawled away.
  • I felt something crunchy underneath my feet, only to see I’d accidentally been stepping on a cluster of snails surrounding rice that was put out to feed the cats.
  • Mosquitos flew around the house as comfortable household members.
  • The walls had holes where pieces of the house seemed to be crumbling out of.
  • Cats and dogs paid each other visits in each other’s homes.

I was no longer in a romanticized part of Cuba. But I knew this was still more comfortable than how many Cubans (or people in other developing countries) live. That night, even in my sleep I was swatting the bugs in my dreams.

Day 7 – La Lisa & Havana Airport

Local taste of Cuba Before Saying Hasta Luego…

The next morning I woke up encased in my perfectly-fitted mosquito net with a fan blowing down on me almost violently.  The towns outside of Havana were quieter and cozier. What did people do for fun? I wondered. Everything was in CUP, the national currency. La Lisa had maybe two restaurants in the entire town which illustrated the lack tourism and disposable income.

A family friend and her newborn were visiting. It reminded me of how Dominican family members tend to drop by unannounced to pass the time. What else would you do without disposable income nor the World Wide Web? You talk to people in person, genuinely enjoy their company, and look forward to hearing about their personal updates. Without a cell phone or constant internet connection, I noticed an improvement in the quality of my conversations. Without Facebook photos or online messaging to form an initial basis of who people were, I savored each bit of dialogue to get to know them better.

We knocked down lemons from their backyard tree while sipping on delicious Cuban coffee. In Cuba, coffee is consumed differently. Like in DR, you drink tiny strong cups of coffee throughout the day. It was black, smooth, strong, and sweet. We finished a nice family meal just in time for my cab ride to the airport in a 1950’s Ford.

In a daze, I wandered through airport immigration. I made new, beautiful, and interesting friends and had experienced one of the most uniquely fascinating countries in the world.

My solo trip was barely that. Thanks, Cuba.


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