A Girl's Guide to Drinking Alone is a blog created by Sammi Katz. I drink alone at bars, then review them for how awesome or awful they are for women to go to alone. Based in NYC.


By Kaitlyn Alkass, Guest Writer for A Girl's Guide to Drinking Alone

I was down in Orlando recently for my brother’s college graduation and the mugginess was glorious. This past winter was my first in New York and while it was nowhere near as frigid as the winter I survived in Bulgaria during my Fulbright year, it nearly broke me. I’ve spent most of my life complaining about the heat and humidity in Florida but now found myself desperately looking up affordable, tropical getaways. I found round-trip tickets from Orlando to Havana for $100. My passport was itching for a new stamp and it was too good a deal to refuse.

The United States’ relationship with Cuba is still complicated despite Obama’s past efforts to lessen hostility. Traveling to Cuba for recreational purposes is not legal, strictly speaking. However, it is evident in the city of Havana that the “Cuban thaw” has taken hold and doesn’t plan on leaving anytime soon. When I was there, I was in support of the Cuban people, meaning I did not give money to government-owned establishments. I instead supported privately owned restaurants and bars and stayed in people’s homes, otherwise known as “casas particulares,” rather than hotels. Traveling to Cuba as an American is like taking a step into the past. Vintage cars from the 60’s drive through Old Havana on their way to pick up tourists at Morro Castle. Teenagers sell internet cards in the park next to carts peddling authentic Cubano cigars. Going to a place that is often vilified in history books due to its ties to communism and the infamous missile crisis, it’s not a place I ever imagined I’d be able to visit in my lifetime. I’m grateful for the opportunity I had to experience the real Cuba, a lively and vibrant country with passionate and kind people.

While I was there with my boyfriend, I did have some alone time where I wandered and let the city take me where it wanted. I felt incredibly safe the entire time I was in Havana, even when I was out walking at 2 or 3 in the morning. Seeing so many solo female travelers in Havana contributed to this feeling of security, although I would say that urban areas tend to be more progressive than their rural counterparts. So, wanna do some good AND get a light buzz going? These are my 3 musts in Havana.


BAR #1: Sugar Bar, Mercaderes 315, Plaza Vieja, Habana Vieja

The Place: An upscale bar that is definitely made for tourists. Located in Plaza Vieja in Old Havana, I get a great view of the cathedral and main square. I also appreciate the A/C.

The Time: Monday, April 29th, around 9-9:30 PM.


The Vibe: Everything is cool and modern, all white and chrome. I feel bad for leaving sweat marks on their nice seats but appreciate the insta-worthy setting and their ornate cocktails. I can imagine Don Draper taking Megan here, but while he was still trying to seduce her. The prices are definitely inflated because it is a tourist-y destination. You’ll find higher prices in Old Havana in general; cruise ships dock here almost every night and thousands of people wearing white capri pants and Birkenstocks roam the streets. I invented a fanny pack rule: the more fanny packs there are, the more expensive the place. However, this means paying about 6 dollars for a mojito rather than 2 so I don’t mind.

The Bartender: A lovely gal who hands me an iPad with the menu on it even though there are menus on the table. I’m not sure what the iPad is for.

The Drank: A frozen mango margarita, piled high in a wide-rimmed glass and garnished with a delicate slice of watermelon. Delish. More smoothie than boozy which is kind of a let down. The alcohol seems to be watered down everywhere I go, or perhaps I am just unwittingly sweating it all out.

Was I Hit On?: No, everyone here is definitely with bae on their bae-cation or too busy taking pics of their drinks for the ‘gram. I see a guy holding a light reflector by a margarita as his girlfriend stands on her chair taking a bird’s eye view with a professional camera. I feel a minor wave of shame wash over me for my poor tagging skills and meager number of followers.

Should You Drink Here Alone?: By all means, treat yoself. Get a margarita the size of your face and sip it on the balcony.


BAR #2: La Vitrola, San Ignacio esq. Muralla, Habana Vieja

The Place: A campy 50’s Americana-themed bar with live music.

The Time: Thursday, May 2nd, 9:30-10PM.


The Vibe: Old time-y 1950’s Americana mixed in with casual portraits of Fidel Castro. It’s just across from Sugar Bar in Plaza Vieja and I want to see if the drinks here are a bit more generous, rum-wise. The place is like walking into an antique shop sans dust and moth balls. There are old record players, vintage Coca-cola ads, jukeboxes, and old-school telephones covering the walls.

The Bartender: A frustrated young man who is visibly annoyed when I don’t order an entree.

The Drank: A frozen mojito with a local Cuban beer on top, garnished with a piece of sugar cane, which I then gnaw on like the heathen that I am. The drink is bursting with mint and crushed ice and the beer adds some nice carbonation.

Was I Hit On?: Nah, this place is more family-oriented. It’s very loud and busy. Don Draper would never take a mistress here, but he might take Betty or Pete Campbell.

Should You Drink Here Alone?: There are better places to drink alone in Havana. But, if you’re in the mood to people-watch and enjoy some live music, Vitrola is your place.


BAR #3: La Floridita Bar, Obispo 557 Esquina a Monserrate, Habana Vieja

The Place: Hemingway’s old hang out and supposedly where he invented the mojito. Why not visit the bar an alcoholic misogynist frequented? The guy’s mom wanted twin girls so badly that she dressed him and his sister in identical clothing and called him Ernestine. I also really love The Sun Also Rises, so I guess I’ll cut the man a break.

The Time: Thursday, May 2nd, 11-11:30PM.


The Vibe: It’s about a twenty minute walk from the main plaza in Old Havana, a hodgepodge of residences and high-end clothing stores. The wending side streets and people standing in their doorways makes me feel like I’m wandering through a small city in Europe. I finally walk inside Hemingway’s place/tourist grotto. This place is absolutely packed. It feels like one of the fancy restaurants Don Draper might have taken his side chicks to for a sexy lunch meeting. There are crystal chandeliers and red faux leather seats with little white cocktail tables. In the corner of the bar sits a bronze Hemingway looking very drunk and happy. Behind his statue is a framed black and white photograph of him posing with Fidel Castro. They also have live music, pretty standard for almost every bar and restaurant in Havana which I absolutely love. The ad hoc band sings popular tunes such as “Guajira Guantanamera” and encourages customers to dance.

The Bartender: A very frazzled Cuban woman. I don’t know how she keeps track of everyone’s tab but she deserves a gold medal.

The Drank: The drank is disheartening. It’s a very sad daiquiri served in a small martini glass. It’s refreshing, like drinking a melted sno-cone, but the interior design of the bar had heightened my expectations. The traditional daiquiri in Cuba is blended ice, rum, and lime. It’s delicious, but again, I wish it had a bit more booze in it. (Do I have a problem?) One thing I notice is tourists carrying their own cups for their drinks at all times. The drinking water in Cuba is not potable, and wary travelers don’t want to risk consuming ice that was made from tap water rather than bottled. I think this is pretty stupid because a daiquiri here is blended ice, but hey, whatever helps you sleep at night. I’m personally uncomfortable with this; I find it insulting.

Was I Hit On?: No, I chat with another American named Connie who looks like she definitely voted for Romney and probably lied about voting for Clinton. She’s nice enough but I become nervous when she exhibits a proclivity toward radical conservative values. My boyfriend then joins us and informs me that he’s made friends with a judge from upstate New York and they exchanged email addresses. It’s precious.

Should You Drink Here Alone?: Absolutely. Just be careful of the shady cab drivers outside, they hike up their prices due to the location.

In short, the drinks are not the main event at these bars. Instead, it’s all about the atmosphere: the music, the dancing, the culture. While the libations were not as boozy as I would have liked, the energy at each venue was absolutely contagious. I can’t hold a rhythm to save my life but I deeply enjoyed watching pro salsa dancers cut through the dance floor like butter, making it look so easy. (It’s not. Put this Baby in a corner or you’ll lose your job, Patrick Swayze.) If you visit Havana, taking advantage of the nightlife is an absolute must. The live music, the decadent voices that can be heard even over the loudest of bar crowds, and the overall nocturnal joviality here is unlike anything I’ve ever experienced. I’ve never walked out of a nightclub before and thought, “Wow, that was so wholesome and heartwarming.”

As a woman, I felt fairly safe, although I did hear from several people that Cuban men take catcalling to new heights. I met a girl from Holland who said she’d received three marriage proposals over the course of two days and that she was very annoyed by all of the unwanted attention. While this could happen anywhere, it’s always important to stay vigilant and be aware of your surroundings.

My top tip for any kind of travel to Cuba is this: make sure you have more cash than you think you need. American credit cards don’t work in Cuba, not even your American Express deluxe ultra-yas-kween black card. I’ve heard horror stories of Americans who had to sell their shoes because they ran out of money and couldn’t use their debit cards to take out cash to exchange! I luckily did not have to resort to that but our flight was delayed at the airport and I didn’t have any money for snacks so I succumbed to a major episode of hangrage. (Hangry but with more rage) As we departed seven hours behind schedule, I sat munching on my 11th bag of those weird purple and orange JetBlue potato chips, wishing I had a melted sno-cone in a martini glass to wash it all down. I’ll never forget the experiences I had in Cuba, and I hope to return soon.

***Editor’s Note*** As of Tuesday June 4, 2019, the Trump administration has imposed new travel restrictions to Cuba, banning the way most Americans typically get to the island. Treasury Secretary Steve Mnuchin said the ban is a response to Cuba’s “destabilizing role in the Western Hemisphere,” but the ban will likely harm the travel industry and the Cuban people, not the country’s government.

Kaitlyn Alkass is a stand-up comedian, writer, explorer and feminist from Orlando. She recently moved to New York City where she lives with her boyfriend in Astoria. She has a Bachelors in English Literature from a liberal arts college, and a minor (major) obsession with Pembroke Welsh Corgis. She lived in Bulgaria for a year teaching English to aggressive teenagers with a penchant for insults and while backpacking through Southeast Asia, she accidentally taught an entire class of Thai children the word “fuck.” Rabies-free since 2017.