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Best Bars in Old San Juan, Puerto Rico

Old San Juan

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.  Keep reading for my list of best bars in 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! If you’re headed to the west coast of Puerto Rico, read my 72 Hour Itinerary to Rincon, Puerto Rico one of my all time favorite places!

6 Best Bars in Old San Juan

Birra & Empanadas

Birra & Empanadas is a small bar with great atmosphere and delicious Argentinian empanadas. Come here to hang, drink a cold one, and don’t forget to try an empanada. (150 Calle De La Cruz)

El Batey

El Batey is a great dive bar! There is graffiti plastered over every inch of wall and light fixtures hanging from the ceiling made from business cards. A serious hole in the wall, but if you love that kind of thing (like we do) you have to check it out.  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)

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.  This place definitely has a lot of character! (151 Calle San Sebastián)

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. 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.  Each of the bars inside La Factoría has a different vibe and its own identity from the next. (148 Calle San Sebastián)

La Cubanita

La Cubanita is a cozy little bar around the corner from busy Calle San Sebastian.  Pull up a bar stool at this traditional style Puerto Rican dive bar and order drinks and food. The vibe here was awesome. (owned by La Factoría) (51 Calle San José)


Barrachina claims they are the inventor of the piña colada. Definitely worth a stop (because hey they 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 but Barrachina should still make it on your list of best bars in Old San Juan. (104 Calle Fortaleza)

piña colada sitting on top of bar at Barracina with little umbrella on top - best Old San Juan bars
Barrachina the inventor of the piña colada | best Old San Juan bars

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. Keep reading to find out what to do while in Old San Juan

Calle Fortaleza

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.

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.

Muns Jewelry

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. 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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  • Charlie Hostettler

    Are you familiar with a roof top bar on Forteleza street in old town San Juan with a great view of the harbor? I was there and found you needed a reservation to get on the elevator and did not get in due to time. I cannot recall the name and would love to make a reservation as I am again going back to San Juan on another Cruise. Thanks

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