As I’m wandering around the 500 year old cobble stone streets at sunset, the air is warm, the sky is a mix of warm yellows and pinks, and the streets lined with apartments of every pastel hue are teaming with tourists and locals alike. I came to Old San Juan with one agenda: bar hop around the city to find the best bars in Old San Juan.
Along the way I stumbled upon cute shops, interesting food, and amazing historical sites. Old San Juan has so much energy! Keep reading for my list of best bars in Old San Juan (this list holds true even after multiple visits to Old San Juan!) and what not to miss while exploring this great city.
While staying in Old San Juan make sure to plan a few days in Culebra, an island off the east coast of Puerto Rico, you won’t want to miss top rated Flamenco Beach! Or maybe you’d like to see the many beaches and wild horses of Isla Vieques?
Heading to the West Coast of Puerto Rico? Read my 3 Day Itinerary to Rincon, Puerto Rico one of my all time favorite places in the world!
7 Best Bars in Old San Juan You Must Visit
Old San Juan is not a very large part of the city of San Juan, Puerto Rico. In fact, you can easily walk around Old San Juan’s cobble stoned streets, bar hop and sight see on foot. All of my favorite bars in Old San Juan are within a few minutes of each other if not right next door!
Legal Drinking Age in Puerto Rico: Eighteen
Can you Drink in the Street in Old San Juan?
Legally, drinking in the street in Puerto Rico with an open container is illegal. (unless, you are at a designated street festival – more on that later) So, while I am not going to encourage you to do anything illegal I will say – drinking on the street in Old San Juan is not uncommon.
1. Birra & Empanadas
Birra & Empanadas is a super small bar in Old San Juan with a great atmosphere and delicious Argentinian empanadas. Come here to pull up a stool and hang at the small bar, drink a cold one (rum and coke would be my pick!), watch music videos and don’t forget to try an empanada! (150 Calle De La Cruz)
2. El Batey
El Batey is the ultimate dive bar in Old San Juan!
There is graffiti plastered over every inch of wall and light fixtures hanging from the ceiling made from business cards. El Batey is a serious hole in the wall, but if you love that kind of thing (like we do) you have to check it out.
Again, we just ordered Rum and Coke’s to drink because they’re so simple but so, so good!
Only downside about El Batey was that almost every person inside enjoying the cheap cocktails was American and thus felt a little unauthentic. (99 Calle del Cristo)
3. La Taberna Lúpulo
La Taberna Lúpulo is an intimate beer hall with a large selection of craft beers on tap. Come and post up at the bar, put back a few and have some snacks off the bar menu. You can also sit at a table and order food.
La Taberna Lupulo is on Calle San Sebastián which has the highest concentration of bars in Old San Juan. This Old San Juan bar definitely has a lot of character! (151 Calle San Sebastián)
4. La Factoría
La Factoría is a cool, urban speakeasy. This was my favorite bar of the night and also one of the most famous bars in Old San Juan! It has even topped lists for best 50 bars in the world and is no doubt one of the best bars in Old San Juan.
You will undoubtedly notice the bar’s popularity from the street but there is no sign on the outside of the bar. Located on the corner of Calle San Sebastian and Calle San Jose, once inside La Factoría don’t be fooled and keep walking through the double doors next to the bar on the right side.
Beyond these doors lay four other bars within La Factoría that you can not see from the street. I decided to enjoy Cuba Libre’s in the salsa room (are you seeing a pattern yet?). Each of the bars inside La Factoría has a different vibe and its own identity from the next. (148 Calle San Sebastián)
5. La Cubanita
La Cubanita is a cozy little bar (and one of my favorites!) around the corner from busy Calle San Sebastian. The outside is very unassuming but once you are inside you will see the charm! It is like you’ve stepped back in time.
Pull up a bar stool at this traditional style Puerto Rican dive bar and order a delicious cocktail. The vibe at La Cubanita (owned by La Factoría) was awesome. (51 Calle San José)
Barrachina claims they are the inventor of the piña colada! There is an argument about who was the first person to invent the Piña Colada. Barrachina AND Caribe Hilton both claim to be the first one to make Puerto Rico’s national cocktail!
Barrachina is definitely worth a stop (because hey they might have invented the piña colada) but to be honest… the frozen piña colada came out of a machine and was not what I was expecting! I’ve definitely have had better (ahem Caribe Hilton) but Barrachina should still make it on your list of best bars in Old San Juan. (104 Calle Fortaleza)
Nono’s is a large bar with open windows to Calle San Sebastian. After we left the first time Brent and I bar hopped around Old San Juan Brent kept saying Nono’s is a No-No. To be blunt the cocktails weren’t good and we didn’t get a very welcoming vibe from Nono’s either.
On our second trip to Old San Juan, we decided to try Nono’s AGAIN! This time it was definitely better and more welcoming BUT our cocktails were straight rum. I’m not sure if the bartender was trying to hook us up or kill us (joking! sort of).
Come to Nono’s for a STIFF cocktail and a true dive bar experience when you are visiting all of the best bars in Old San Juan, Puerto Rico.
Visiting Old San Juan during San Sebastian Festival
Fiestas de la Calle San Sebastián (San Sebastian Street Festival) is Puerto Rico’s largest festival and concludes the holiday season in Puerto Rico (the longest in the world!). The festival is a multi-day affair with live music and concerts, parades, dancing in the street, local artisans and art and lots of partying.
Brent and I went to SanSe (what the locals call the festival) in 2023 and had the best time walking around Old San Juan, ducking into bars for drinks, watching impromptu dances in the streets, listening to live music in squares and eating from street vendors.
Expect a lot of people and large crowds for the San Sebastian festival. We heard people comparing the festival to Mardi Gras in New Orleans, Louisiana. Calle San Sebastian is especially crowded at this time of year with loads of people partying in the street.
SanSe Festival typically happens on the third weekend every January and runs from Thursday to Sunday.
Exploring Old San Juan
If you are up for it, all of Old San Juan is discoverable on foot. I believe this is the best way to explore any new city and discover what makes it tick. Walk down side streets and stumble into a small cafe or bar you wouldn’t have found anywhere on the internet. For a full list of things to do in Old San Juan you’ll want to read this guide here.
Head to Calle Fortaleza the most famous street in Old San Juan. The old cobble stoned street is lined with beautifully panted pastel colored buildings. At the end of the street you will see the Governor’s mansion. This is a great spot for a photo op and in the surrounding neighborhood there are lots of shops and restaurants to enjoy.
San Juan Bautista Cathedral & Puerta De San Juan
While walking around Old San Juan, don’t forget to walk past the San Juan Bautista Cathedral. This beautiful cathedral is in the center of Old San Juan on Calle de Cristo and is definitely worth walking by or walking into! If walking near the harbor don’t miss Puerta De San Juan. The gate was constructed in 1635 and served as the main entry into the walled city during the Spanish colonial era.
Must Read: The 17 Best Things to do in Old San Juan
Castillo San Felipe del Morro
Castillo San Felipe del Morro, the historic fort of San Juan is a must. El Morro (for short) is set on top of a cliff overlooking the Atlantic ocean at the entrance to San Juan Bay and dates back to 1589. The fort was constructed to keep the Spanish colonial port safe from enemies.
Over the centuries the fort was added to and became much bigger than the original plans. Today the site is a National Park, a World Heritage Site and preserved as a museum. Come here to learn a bit about San Juan and Puerto Rican history. The views alone are worth the visit.
Castillo San Cristóbal is another fort not far from Castillo San Felipe del Morro. We ran out of time and weren’t able to get here. If you loved El Morro, definitely check out Castillo San Crisóbal as well.
Try a Mallorca
You must try a mallorca while visiting San Juan! A mallorca is a traditional sweet bread with powdered sugar sprinkled on top. You can eat it alone, with butter and jam or I had a ham, egg and cheese on a mallorca at the counter of a traditional Old San Juan diner called Cafeteria Mallorca. You can sit down and enjoy a meal or you can buy pastries out of the front window.
While wandering the streets, I stumbled upon the cutest boutique called Muns Jewelry. They have lovely dainty gold plated and silver jewelry and a selection of awesome vintage clothing in the back! @munsjewelry
- Be adventurous! Don’t rely on Yelp or Trip Advisor. Our favorite places we found were by wandering around the streets.
- Talk to locals. We found a lot of valuable information and tops by talking to our Uber drivers.
- San Juan is a really quick and easy flight from the US. You can find good deals on flights. Plus Puerto Rico is also close enough for a long weekend trip!
- If you want to stay in Old San Juan, book an Airbnb – there are a lot of great options for all price ranges.
- If you prefer a hotel, try to find one near Isla Verde or Condado. This is the nicest beach in San Juan and only a quick cab ride into Old San Juan.
Headed to Puerto Rico? Don’t forget to include the island of Culebra and/or the surf town of Rincon in your vacation plans!
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