Spend a day exploring Old San Juan in Puerto Rico

By: Lauren Hill

October 28, 2015

With around 500 years of intriguing history, Puerto Rico’s capital San Juan is a fascinating place to visit, and where better to see it for yourself than the old walled city. Spend a day exploring Old San Juan’s cobbled streets and soak up its distinct culture, from heritage that dates back to the 16th century, to the arts, music and food of today. We take a look at the best things to do around this pocket of Puerto Rican culture.

Surely the best way to discover the charm of Old San Juan is to navigate its cobblestone streets on foot, while stumbling across plazas. As the second oldest European-founded city in the Americas, this Caribbean harbour town displays its fascinating past through its 16th and 17th century colourful colonial architecture and ancient stone forts that look out to sea.

Exploring Old San Juan | El Morro Explore the historic sites of Old San Juan, including El Morro © iStock / eddtoro

Castillo San Felipe del Morro, more widely known as El Morro, is one of the largest forts to have been built by the Spanish in the Caribbean, situated high up on a promontory overlooking San Juan Bay. The fort Castillo San Cristobal is at the eastern gate of the walls that surround Old San Juan, and close to El Morro, on San Sebastién Street, sits La Casa Blanca, a preserved 16th century house and one of the oldest buildings on the island, with gardens to get lost in.


With so much history, the old town has a number of museums to spend some time in. Just across from El Morro, the Ballaja Barracks Building – constructed by the Spanish military with housing, stables and dungeons – is now the setting for a number of cultural venues, with a music school and dance school, as well as a museum.


Art galleries are dotted throughout the old town, too. Cruz Street is home to Obra Galeria, which exhibits work by contemporary painters and sculptors, while Galeria Exodo on Cristo Street focuses on the work of Caribbean artists. On San Francisco Street you’ll find Siena Art Gallery, which along with its collection of paintings, includes Puerto Rican arts and crafts.

Exploring Old San Juan | Old San Juan Look out to sea from the walls of Old San Juan © iStock / Sean Pavone

Take a break from exploring the maze of streets by calling into one of the old town’s top cafes. Caficultura overlooks Plaza Colon and is a well-known favourite for its artisanal coffee. Cuatro Sombras is another one to head to for coffee gourmands, as the owners take pride in serving up farm-to-cup coffee, with its own roaster and coffee tasting sessions.


Before you leave, don’t forget to pick up some souvenirs. For plenty of choice, take a walk along Fortaleza Street, which is lined with shops selling items such as carved wooden figurines, Puerto Rican coffee and handmade jewellery.


By now you’ve probably worked up quite the appetite. Luckily the old town has no shortage of inviting eateries, and in a city that’s known for its nightlife, there’s an abundance of bars, too. To try local Puerto Rican culinary specialities, as well as to find more international offerings, stay on Fortaleza Street. As well as a hub for souvenir shops, the street is famous for its abundance of restaurants, among which you’ll find some of the city’s best.

Exploring Old San Juan | The Parrot Club Settle in for a drink and a bite to eat at The Parrot Club © Flickr / cogito ergo imago

The Parrot Club restaurant and bar is one to take note of for its live Latin jazz and salsa, “˜nuevo Latino’ cuisine and cocktails, which can be savoured in the palm-filled courtyard. Carli’s Fine Bistro & Piano is also well known for its live jazz, owned and operated by jazz musician Carli Muoz. This refined restaurant and bar tempts passers-by in for glamorous cocktails and Caribbean tapas. Of course, you can’t leave Puerto Rico without having first danced in its salsa bars. There’s plenty of live salsa music to enjoy in Old San Juan, but perhaps the best known salsa venue is Nuyorican Café, which has regular live music performances.


If you’re in town at the right time of year, experience the Puerto Rican love of both music and food during the Old San Juan SoFo Culinary Fest. Around South Fortaleza and its surrounding streets, restaurants take part in this five-day event by setting up their own street food stalls, while live Puerto Rican music is performed across eight stages. After immersing yourself in the island’s vibrant festival spirit, you know you can return home having experienced Old San Juan at its best.

Exploring Old San Juan | Old San Juan Walk between the coloured houses of Old San Juan © iStock / shakzu

Booking a trip to San Juan? Our codeshare arrangement with Delta makes it simple for you to travel all over North America, bringing Puerto Rico within easy reach.

Where would you recommend to visitors exploring Old San Juan? Let us know in the comments section below.


Header image: Walk along the cobbled streets of Old San Juan © Flickr / Tiago 

Written by Lauren Hill


Lauren Hill

Between living in Japan, Singapore and London, Lauren has spent the past few years working as an editor, sub-editor and travel and lifestyle writer, with a focus on luxury and adventure travel. She is currently based in London, exploring the city’s eating and drinking scene and seeking out its outdoor green spaces.

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