Rich History & Incredible Nightlife of Old San Juan, Puerto Rico

Advisor - Jackie Garraffa
Curated By

Jackie Garraffa

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  • USA

  • Puerto Rico

  • San Juan

  • Arts & Culture

  • Beaches

  • Boutique Travel

  • Domestic Travel

  • Food & Wine

  • International Travel

  • Foodie

  • Relaxation

  • Sightseeing

Advisor - Rich History & Incredible Nightlife of Old San Juan, Puerto Rico
Curator’s statement

There is no place quite like Old San Juan. Watching the sunset over the water from the Castillo San Felipe del Morro is a dream. San Juan is a city rich in history, architecture and of course, incredible eats. Old San Juan — just a few blocks away from its commercialized neighbors, Condado and Isla Verde — and its historic center, is known for pastel hued houses that line its cobblestone streets featuring fun bars, boutique shopping, and a plethora of Caribbean-fusion restaurants. It is on these streets that internationally-ranked Reggaeton is born, where salsa and merengue are danced at all times of the night, where mofongo (plantain mash) smells fill the alleyways, and life is lived a little bit more intensely.

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Where to stay in Old San Juan, Puerto Rico

Hotel El Convento

Long-time favorite in Old San Juan, with a traditional look and access to a sister beach club.

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  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Condado Vanderbilt Hotel

Art Deco beauty with a mix of heritage and modern rooms, most with Atlantic Ocean views.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

La Terraza Hotel San Juan

Hillside boutique hotel in the heart of Old San Juan.

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Things to do in Old San Juan, Puerto Rico

Rich History & Incredible Nightlife of Old San Juan, Puerto Rico - Things to do


No trip to Old San Juan is complete without learning about its rich history. From naval battles, old prison cells, pirate attacks, the world's most narrow apartment, and cobblestones that are made from the broken pottery, there is a whole world in the small city of San Juan. A visit to the Castillo San Felipe del Morro and the fort offer swoon-worthy views of the Caribbean Sea. 

Puerto Rico also has a rich history rooted in both Afro-Caribbean and Indigenous culture, and there are plenty of opportunities to learn more, such as through the Taína route.


The nightlife scene in San Juan, Puerto Rico is a story of its own. Bar-hopping on a Thursday night is a must in Old San Juan, and it's not the college stereotype; it's a serious task to identify and taste-test all the cocktails in town. Specifically, Old San Juan is home to the piña colada, and is also one of the best places for amazing fresh mojitos and sangria. However, visiting the local cocktail bars will provide much more than just a party with amazing drinks – San Juan nightlife has history, art, amazing tapas and are run by friendly locals or boricuas.

The famous La Factoria is a speakeasy and an absolute must (no sign on the door, you have to know where to find it!), La Barrachina for the original piña colada (don't forget to try the mofongo as well!), and Marilyn's Place for the best mojitos, and an unforgettable local experience.

Many bars and dance clubs are on Calle San Sebastian, so take a paseo down the street to experience the best of Old San Juan after dark.

Places to eat & drink in Old San Juan, Puerto Rico

Rich History & Incredible Nightlife of Old San Juan, Puerto Rico - Places to eat & drink

Old San Juan is home to some of the best Puerto Rican and Caribbean fusion cuisine - foodies will love it! Authentic Puerto Rican eats and delicious seafood is everywhere you look, but Old San Juan is also home to great Italian, Mexican and Asian-fusion restaurants. From local eats to Michelin-starred restaurants and everything in between, take a tour of the fantastic Puerto Rican Cuisine. There is something for everyone.

Cafe Berlin: A must-visit local eats and wonderful cocktails destination, it is also a perfect spot for brunch if you are looking for authentic Puerto Rican food with a twist! The restaurant features a unique and inventive menu that has tons of vegetarian and vegan options. (Try the vegan mofongo, dulce de leche pancakes and the tamarind mimosas!)

Ajo Del País: Dine with the locals at this authentic joint.

Chocobar Cortes: The best restaurant, coffee shop and chocolate museum in one! The fresh butter, chocolate coffees and cocktails are inventive and absolutely delicious.

La Casita De Rones: To get away from the nightclubs, try this historic rum bar that has inventive cocktails and doubles as a souvenir shop.  

Triana Tapas and Flamenco: A unique spot with great food and live music every evening. As the name hails, there is a flamenco show every Thursday through Sunday, where guests dance with the performers.

Mercado La Carreta: Premier brunch spot for traditional fare with a Latin twist. Stop by for a latte too!

La Factoria: Named one of the best bars in the world and site of the famous “Despacito” music video, this is a must when visiting Old San Juan. The bar is made up of several rooms with dance floors and djs playing different genres of music. Each bar space has its own flare, but they all make absolutely delicious craft cocktails.

El Batey: If legendary dive bar, vintage jukebox, poker-faced bartenders and graffiti on the walls from the 60s excites you, then El Batey is easily the best nightlife option for you.

La Placita de Santurce: Historically, this was two-tiered market square locals shopped for fresh produce, but today it has numerous iconic restaurants and street vendors, making it buzzing late-nighthangout spot.

Need to Know

Old San Juan is a charming port town, which also happens to host quite a few cruises. I advise that you book some must-visit destinations ahead of time. And while the town is crowded, you can plan a day trip to escape to the El Yunque rainforest or weekend excursions to the Culebra or Vieques islands for kayaking.

Advisor - Jackie Garraffa

Travel Advisor

Jackie Garraffa

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