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Vacation in Puerto Rico: Why More Lesbian Vacations Should Happen Here


I mean we’re beautiful, the island is beautiful that’s a pretty good place to start in my opinion. I visited Puerto Rico for the first time this winter. As an American, specifically and American based on the east coast admitting that sounds almost ridiculous. That’s part of the problem, not enough Americans are considering a vacation in Puerto Rico! Sure, we’re going to the Caribbean in huge numbers but why aren’t more of us visiting Puerto Rico? 

When we look specifically at LGBTQ travel and lesbian vacations, Puerto Rico stands out even more as an outstanding choice. Many parts of the Caribbean are as well known for their homophobia as they are for their crystal clear waters. It is still illegal to be LGBT in 11 countries in the Caribbean. Many others still remain incredibly difficult for queer people to enjoy when off the big-name resorts. Puerto Rico has had marriage equality since 2015, employment protections, and is overall very LGBT friendly, especially in the city of San Juan. If you are looking to enjoy the incredible weather, blue water and white sand beaches of the Caribbean as a queer person start with Puerto Rico. 

Special thank you to the incredible folks at Discover Puerto Rico for putting this trip together and for being a leader in LGBT travel, especially for lesbian and queer women. Also a huge thank you to the ladies of  Once Upon a Journey, for always taking some of my favorite photos of myself. Traveling with other creative, talented, and passionate people made this trip even more unforgettable. 


Fun Facts About Puerto Rico

Puerto Rico is a US Territory

There are a  handful of reasons that make a vacation in Puerto Rico super convenient. Reason one, you don’t need to have a passport to visit as a US citizen. While I certainly encourage everyone to get a passport if you don’t have one and want to visit the Caribbean its $145 per person less to go to Puerto Rico than in other countries. 

The second reason, Puerto Rico operates on the US dollar. That means you don’t have to exchange any money or learn an exchange right to understand prices. Even though it is domestic travel I encourage you to set up a travel notice with your bank. 

Third, your cell phone will work here. When you’re in Puerto Rico your normal cell service applies. You won’t be forced to pay international data fees. 

Jungle Bar Photo by Once Upon a Journey


The drinking age in Puerto Rico is 18 rather than 21. 

Roughly 70% of the run in the US comes from Puerto Rico. Casa Bacardi is the largest rum distillery in the world. Yes, you can visit but more on that later. 

The Pina Colada was invented in Puerto Rico. Although there is quite some debate as to who the original creator was. 

Language in Puerto Rico

Spanish is the language the majority of Puerto Ricans speak. As a US Territory technically both Spanish and English are the official language. Many people understand English is a higher rate than they speak it so do not hesitate to ask questions.

Getting To Puerto Rico

There are tons of flights to Puerto Rico from all over the United States. With so many options of departure times and cities, your Puerto Rico vacation is more accessible than ever. The flight from New York City to San Juan is slightly over 4 hours and from Miami it’s 3hours. That means you spend less time in transit and more time kicking back with a cocktail. 

Where to Stay in San Juan 

The city of San Juan is relatively compact. If you stay in one area you’ll have little to no issues moving about to visit the attractions you’re most interested in. However to make deciding where to stay in San Juan I’m breaking down three awesome neighborhoods. Again, San Juan as a whole is an awesome lesbian vacation destination. These neighborhoods are just my favorite. 

Queer women in Old Town San Juan

Old San Juan 

Old San Juan is probably the image in your head of Puerto Rico. This part of the city is the cultural center. It’s where you’ll find beautiful colonial architecture and cobblestone streets. Staying in an Old San Juan hotel means much of what you’ll want to see is walkable. Both a pro and a con is that this area is set up for tourism. While there are restaurants, bars and shopping it has a bit less local vibe. 


Condado is a strip of land that separates the Condado Lagoon and the Atlantic Ocean. In many of the hotels here you’ll see water no matter which side of the building your room is on. It is the most centrally located of all the neighborhoods, just a short Uber ride from both Old San Juan and Santurce. The neighborhood is filled with luxury hotels, oceanfront restaurants, and some really great shopping. It’s a great option for any LGBTQ traveler because there’s a gay beach and some of the best gay bars in Puerto Rico are here. The downside here is that you’ll have to take more Ubers than in Old San Juan. 


This is the newest of the San Juan neighborhoods on this list. The area is trendy, with art galleries, murals, and boujee coffee shops. I think it’s fair to say this is San Juan’s hipster neighborhood. The nightlife options are seemingly endless. My favorite part is a mix of locals and tourists. You’ll hear music pumping and see people flowing from bar to bar dancing in the streets. Because Santurce is more local and a bit of a newer destination there are fewer accommodations to choose from. If this is the right neighborhood for you I’d recommend checking Airbnb

Old San Juan Hotels 

Hotel El Convento 

You won’t find many hotels with a history as interesting as Hotel El Convento. Yes, you guessed in before becoming a luxury hotel, the building was, in fact, a 16th-century convent. This Old San Juan hotel is right in the heart of everything. If you’re the type of person that likes to wander aimlessly through the city streets this it the perfect location. They also have a beautiful courtyard. If you don’t stay here definitely plan to stop by and enjoy lunch in the courtyard. 

La Terraza Hotel

The one and two-bedroom suites at  La Terraza de San Juan give you a little extra space to stretch out. The individually styled rooms are located in two Spanish-Colonial Style buildings. Again, located in the heart of Old San Juan you have great access to some of San Juans’ best restaurants, bars, and attractions. If you just want a chill day, take advantage of the plunge pool and stunning rooftop patio. 

Caribe Hilton

I’ve found that when it comes to LGBT hotels you can almost never go wrong with Hilton. The Caribe Hilton is a wonderful choice for any queer traveler visiting San Juan. This oceanfront spot went through a total renovation that was completed in 2019. There are six restaurants and bars on-site, one of them even claims to have invented the pina colada

Gallery Inn

Consistently considered one of the best hotels in San Juan The Gallery Inn provides ocean views that simply can’t be beaten. This boutique hotel is set up on a hill in a Spanish Colonial-style building. Everything about the Gallery Inn is oozing with personality and charm. One of the coolest parts is the panoramic city view at night. 

Condado Hotels 

La Concha 

If you’re looking for “the” gay San Juan hotel, look no further than La Concha. You can always expect to see other queer people during your stay. Much of that has to do with its location directly next door to the most popular gay beach in San Juan. The beautiful infinity pool and poolside bar make for the perfect place to relax. They also offer free bike rentals so make sure to take advantage of that. 

Serafina Beach Hotel 

The Serafina Beach Hotel is bright, airy and modern. The rooms have floor to ceiling windows letting you take advantage of the incredible ocean views. The stunning infinity pool is a great place to take a dip or get a tan. They also have a beautiful restaurant that makes some great cocktails. This is a great option for LGBTQ travelers because its close to the gay beach and LGBTQ nightlife. 

Condado hotel room

Atlantic Beach Hotel

Another great beachfront Condado hotel option is the Atlantic Beach Hotel. The vibe is chill and laid back the kind of place just inviting you to kick back and relax. There are a bunch of good food and nightlife options within walking distance so you can skip the Uber. 

AC Hotel by Marriott

The AC Hotel by Marriott is within a short walking distance to much of San Juan’s LGBT Nightlife. The rooms are big and comfortable to come back to after a night out. The rooftop pool and bar is a really cool switch up from many other hotels in the area. 

Things to Do in San Juan Puerto Rico

Puerto Rico is approximately the size of Connecticut making it totally possible to see multiple cities in a week’s stay. It is easy to rent a car from the familiar rental car companies and explore all over. While places like Culebra and Rincon have their own stories to tell I’ll be continuing to focus on all the incredible things to do in San Juan. 

Old San Juan Things to do

Old San Juan is the kind of place you take your camera in and out of the bag a hundred times before stringing it around your neck and embracing the tourist look. There are just too many beautiful nooks and crannies begging to be photographed. The Spanish Colonial architecture and splashed with colors of the Caribbean make Old San Juan absolutely stunning. Simply wandering through the cobblestone streets popping into shops and restaurants is enough to keep you happy for days on end. 

History in Old San Juan

For very good reason el Morro and Castillo de Cristobal are two of the most popular attractions on the island. Two massive and stunning military fortresses designed to protect the city. They are both incredibly rich in history. While completely stunning to see from land try getting out on the water for a completely new perspective on their size. 

Old San Juan Puerto Rico

Take a walk along Paseo de la Princesa on the Southern side of Old San Juan. Along the walk, you’ll see historical statues, beautiful gardens, and handcraft kiosks. Especially on the weekends, there is a really fun mix of locals and visitors. 

There are also a ton of phenomenal museums in Old San Juan. Some of the best include the Museum of the Americas, National Gallery, and San Juan Museum. For a full detailed list of museums in Old San Juan check here

Best San Juan Beaches

It is a well-known fact that the beaches in Puerto Rico are world-class. They are known for the incredible white sands and bright blue waters. A vacation in Puerto Rico just isn’t complete without some time on the beach. While there are no beaches located in Old San Juan there are many incredible spots in other parts of the city. I listed some of my favorites but keep in mind Puerto Rico has 248 official beaches. 

San Juan beaches

Isla Verde Beach

For a peaceful and exceptionally clean beach option visit Isla Verde Beach. This San Juan beach gives you plenty of room to spread out even on a busy day. It’s a great spot for swimming and even surfing. If you’re looking for a little adrenaline rush look into renting some jet skis. 

Escambron Beach

Looking for some good snorkeling, look no further than Escambron Beach. By all accounts, this is one of the best beaches in all of San Juan. Big palm trees overhead make this beach visually impressive while also offering some much-needed shade. Escambron Beach is within walking distance to the historic Bateria El Escambron and Third Millenium Park (tons of good food). 

Playa Ocean Park

Without a doubt, the most popular of the San Juan beaches are Playa Ocean Park. This beach is perfect for pretty much everyone. There are times when it gets busy with tourists but there is distinctly fun energy found here. The sands are white, the water is super blue leaving you feeling like you’re living in a postcard. Try to grab a couple of empanadas from the local vendors. They are super delicious. 

Condado Beach

For me, this is absolutely a case of best for last. Condado Beach is the gay beach in San Juan. It is located directly in front of the Atlantic Beach hotel. The beach itself is easily accessible and you can rent umbrellas and sun loungers once you’re there. 

queer women walking on the gay beach in Puerto Rico

As a gender non conforming person trips to the beach can be stressful. For me, most of that stress comes from often being perceived as male. Obviously, once I am in a swimsuit it quickly becomes clear that is not the case. At times that moment is met with wandering eyes other times with anti LGBT slurs.  While I found Puerto Rico to be incredibly welcoming to LGBT people being on the gay beach gave me additional peace of mind. I knew I could splash in the waves with my friends without worrying. As mainstream acceptance continues to grow more and more queer spaces like our lesbian bars disappear. This is just another example of why queer spaces are so important. 

androgynous woman in the ocean behind a big wave
Once Upon a Journey

Try Puerto Rican Coffee

When you think of Puerto Rico chances are your mind instantly transports you to one of two places Old San Juan or a pretty beach. Both of those images are correct but what you might not know is the middle is quite mountainous. The interior of the island is filled with mountains and a thick rainforest also known as perfect growing conditions for coffee beans. Puerto Rican coffee is known to be a touch sweet and really smooth. 

There are three great ways to experience Puerto Rician coffee during your visit. The first is to visit a coffee plantation directly. During your visit, you’ll get a better understanding of the history, process and of course a taste. The second is to buy some coffee and make it for yourself. These are the best Brands of Puerto Rican coffee to look for. Not only is it nice to sip on in the mornings it’s the perfect souvenir for you or someone back home. 

The third option and probably my favorite are to sip your way through as many coffee shops as possible. These San Juan coffee shops know how to handle the beans perfectly and will undoubtedly deliver a great cup. The most common way to enjoy Puerto Rican coffee is to order a cortadito or cafe con leche. Below are a few of the best coffee shops in San Juan. 

Puerto Rican coffee shop

Gusto’s Coffee Company

Gusto’s Coffee Company is serving up in house-roasted beans. They have a great espresso-based menu for you to relax and enjoy. If you’re with a group I encourage everyone to try something different. 

Hacienda San Pedro 

The beautiful Hacienda San Pedro is located in the heart of the arts district. They are serving coffee straight from the farm in the Jayuya Mountains. One of my favorite things is that after you have a cup you can buy a bag of coffee to take home. 

Cafe Cola’o

Cafe Cola’o is located right in Old San Juan so drop a pin for when you’re out wandering and need a midday to pick me up. Some of the best baristas in the city work here so get ready for some latte art made Instagram stories. It is tiny inside so finding a table can be tricky if you hit it when it’s busy. Everythings locally grown and delicious so even a to-go cup makes it worth the stop. 

Cafe Dan Ruiz 

More locally roasted beans, hopefully you’re catching on to the theme here. Cafe Dan Ruiz has great coffee and some really delicious breakfast options. The vibe is super chill and the prices are great. The roasting facility is on-site so the first thing you’ll notice is that incredible coffee smell. 

Explore Santurce

Santurce is San Juan’s coolest neighborhood. The first thing that catches your eye is the murals. Practically everywhere you turn in here there are murals to check out and of course, take photos of. You can take a tour of the murals but I recommend just wandering and seeing them on your own. There is something special about turning the corner to find one of these massive, vibrant murals. Before you even ask, yes, Santurce is safe. The neighborhood is a bit more local and has a bit more grit than what you’ll see in Old San Juan. In the same way that Brooklyn has more grit than Midtown. In my opinion a good thing. 

Santurce is trendy and artsy. With great restaurants, coffee shops and art galleries sprinkled throughout. When the sun goes down the nightlife gets rolling. The parties often spill into the streets everyone happily dancing with a drink in hand. The vibe in Santurce is just different, in a good way. I’d recommend blocking off a whole day to spend here

Visit the Bacardi Factory Tour

Over 70% of the rum in the US comes from Puerto Rico. It’s not surprising that Casa Bacardi is the largest rum distillery in the world. I am by no means a rum connoisseur. The truth is I drink very occasionally. I say this because as a non-drinker I still had an amazing experience at the Bacardi Factory. Even if you’re thinking “rum isn’t my thing” I encourage you to give it a try. 

queer women on the Bacardi Tour

The Bacardi Factory offers multiple tour options. Each of various lengths, focal points and of course prices. The Historical Tour, of course, talks about the history of the family-owned business and the distilling process. The Rum Tasting tour gives you the opportunity to taste six of the premium rums. If you’re curious to learn about rum on a deeper level this is the tour for you.  The last tour offered at the Bacardi Factory is the Mixology Class. In the mixology class, you get the full bartender set up and learn to make three classic drinks. I did the combination of the Historical Tour and Mixology class which ended up being perfect. I can’t recommend the mixology class enough. While I probably won’t get hired as a bartender for any upcoming events I had so much fun. Make sure you have a little something to eat before getting there. The Historical tour comes with a welcome drink and the Mixology class gives you three airplane bottles of rum per person. 

Taste Puerto Rican Food

Eating is an integral part of understanding a new culture. Puerto Rican food is no different at all. The blend of ingredients and cooking techniques begins to tell the story of the island’s history. You’ll have ingredients like yucca that are indigenous to the island, the Spanish brought olives and cod. When Puerto Rico became a hub of slave trade African spices and cooking techniques were introduced. Puerto Rican food is bold, it’s vibrant and incredibly flavourful. There is a full food guide on its way but for now, here are a few Puerto Rican foods you have to try. 

fried Puerto Rican food


Tostones are thinly sliced and fried plantains. They’re easy to find and can be dipped in all sorts of things from ketchup to garlic aioli. You’ll typically get them as a side dish. Cafe El Punto makes some great ones but honestly, they’re pretty easy to find. 


Trying to explain mofongo is tricky especially if you’ve never had a plantain. For starters, mofongo is a heavy dish. It is made using green plantains that are fried and then mashed. Once they are mashed a variety of broth, spices and flavors are added. The most typical include salt, garlic, and olive oil, of course, this is when many people get creative. That mixture is pressed in a tight ball and served with roasted meat and broth. Check out El Jibarito in Old San Juan to dry a delicious mofongo. 


Whole roasted pig is an essential part of events in Puerto Rico. Taking a prized position at the table for all big celebratory events. The best way to taste it is to get out of the city. Take a bus or uber and visit Ruta del Lechon or Pork Highway. It’s exactly what you think an entire road lined on both sides with open-air restaurants. Enjoy your Lechon and all sorts of incredible sauces and sides. 

Arroz Con Gandules 

The national dish of Puerto Rico has to make it on the list. You can find Arroz con gandules all over the island. It’s made with white rice, pigeon peas, capers, olives, tomato sauce, and sofrito. The sofrito is made of cilantro, onions, peppers, this is the foundation of flavor in the dish. It’s worth a try even if you aren’t much of a cilantro fan. 


Adventure with El Yunque Tours 

Puerto Rico is home to the only tropical rainforest in the national park system, El Yunque. While there are plenty of things to do in San Juan I encourage you to escape into the jungle even if only for a half-day. There are tons one El Yunque tours to choose from. Some of the highlights include waterfall treks, ziplining and riding ATVs. 

queer people dressed in helmets to zipline

While I was there I visited Rainforest Zipline Park. The zipline track was beautiful and the guides were incredibly helpful. It was so much fun to hear them encouraging the more nervous members of our travel party. A park is a great option for someone who is doing a zipline for the first time. The first few lines are pretty tame eventually building up to a couple longer and faster. 

person on a zipline

After a morning spent on the ziplines getting the adrenaline pumping, we decided to keep it going at  Carabali Rainforest Adventure Park. They offer ATV and horseback riding tours through the jungle. It’s important to note that you do need to show your driver’s license in order to drive the ATVs. I am terrified to drive anything so luckily I was able to hop hop on the back with my friend Alysse from Ready to Stare. Our guide for the hour-long ride was awesome. He even graciously offered to play photographer while we took all sorts of group shots. Plus he scooped up some passion fruit along the way for us to try. 


Gay Bars in Puerto Rico

There are undoubtedly more gay bars in Puerto Rico than in many much bigger US cities. Like pretty much everywhere in the world these gay bars welcome all shades of the LGBTQ rainbow however it is a much more male leaning crowd. You can find lesbians sprinkled about more so attending specific parties than specific bars. Here are a few of the best places to check out. 

Lesbian Bars in Puerto Rico

Flavor, A Pedir De Boca, El Cojo, and La Esquina de Polo are a cluster of bars located side by side a bit further south in San Juan. The crowd is young, queer and local. We danced, sipped the local beer Medalla enjoyed flowing from bar to bar. The crowd seemed to be very similar in each but it’s worth checking them all out. The other great resource for queenright life is Jhoni Jackson. When we visited she was in the process of opening a new queer bar and host a ton of parties. Check her out on Instagram for more information on what might be happening during your visit.

Oasis Tapas & Lounge

Oasis is a really cool and welcoming local bar. It’s a great place to stop in for a few drinks during their happy hour. They have a whole bunch of two for one special so it’s a perfect place to start the night. 

Circo Bar

Ciro Bar is the most popular and crowded of all the gay bars in Puerto Rico. Circo Bar has really popular drag shows featuring some of the most popular queens in Puerto Rico. Keep in mind you’re in Latin America and bar nights start late. Don’t plan on showing up to this Santurce hot spot before 12-1. 

El Bar Bero

If you’re into great drinks, think about a stop at El Bar Bero. My favorite part is that the decor makes you feel like you are in a barbershop which happens to be one of my very favorite places

lesbians under a rainbow arch in San Juan




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