Old San Juan

Stroll through Old San Juan’s cobbled streets and see the city through fresh eyes. (Photo: Alamy)

Puerto Rico

5 Things to Do in Old San Juan Beyond the Castillo

Visiting Puerto Rico? One experience all travelers to the island should have is exploring Old San Juan, a historic district dating to 1509, when Spanish settlers arrived.

The most popular attraction in the area is undoubtedly Castillo San Cristóbal, a fort completed in 1783 by the Spanish to protect the city. And while you should certainly visit the site, it’s important to explore beyond to experience the other wonderful things Old San Juan has to offer.

1. Wander with Open Eyes

One thing that makes historic Old San Juan so charming is its array of pastel-colored Spanish colonial architecture paired with peaceful squares. It’s the second-oldest city in the Americas, and a stroll up and down its cobbled streets offers a window into the island’s past — and present.

Blending with well-preserved history is the slower pace of island life, so don’t feel guilty for grabbing a Señor Paleta ice cream (don’t miss the Strawberry Cheesecake!) and just enjoying the sun.

The main squares are Plaza de San Jose, where you’ll see a statue of Juan Ponce de León; the bustling Plaza De Armas, with murals and sometimes live performers; Plaza Colon, which honors Christopher Columbus; and the waterfront Plaza Dársenas.

2. Get Creative

Old San Juan has no shortage of arts-focused offerings, like Galeria Botello. If you’re really looking for inspiration, Poet’s Passage is half café, half poetry gallery, with inspiring plaques covering every shelf and wall. On Tuesdays at 7 p.m., they host open-mic poetry nights in a chill, sofa-filled space.

3. Imbibe

Wandering Old San Juan, you won’t need a plan for drinks; almost every two feet you’ll find another bar — many with outdoor seating — offering inexpensive cocktails and two-for-one glasses of sangria.

If you’re looking for a special imbibing experience, however, you’ll want to have a plan. For beer drinkers, La Taberna Lúpulo is craft-beer heaven. Inside you’ll find locals and visitors beating the heat and sipping their Bell’s and Victory beers for hours, though you may want to opt for one of the quirky beer cocktails.

Tip: The Perla Punch is amazing, blending fruit juices, lemon and coconut rums, and ale. Another cocktail spot, the unpretentious, speakeasy-like La Factoria, is where creative libations and live music meet.

4. Eat Local

old san juan
Eat like a local at Deaverdura. (Photo: Jessie Festa)

With so many great restaurants — both local and international — it’s hard to decide where to eat. Because Old San Juan is so tied to history and culture, it’s smart to opt for a truly local meal.

At Deaverdura, you’ll listen to Latin music in a lively, lime-green-splashed space. The bar is lined with coconuts, a perfect meal accompaniment. There’s no paper menu; instead your server will recite the offerings — fried chicken, pork chops, fresh catch, roast pork, pasteles — and each includes beans, rice, an optional plate of fried plantains (tostones) and a selection of homemade sauces.

5. Get to Know Artisanal San Juan

Wherever you travel, you should aim to go local and support the community you’re in. Luckily, Old San Juan offers a number of ways to do this. For unique, affordable souvenirs, try The Artisan Corner Everything, from the wine-laced candles to the pineapple coffee to the handmade soaps, is made by Puerto Rican artisans.

Another suggestion: Café Cuatro Sombras. Here you can order from the counter or coffee lab, or sit in the rustic café or on the back patio with its climbing vines. No matter what ambience you seek, your cup will be filled with 100% Puerto Rican coffee.

Say goodbye to cheap keychains: You can even buy a bag to bring home for a local souvenir.

Marriott International recently invited a group of travel bloggers to visit Puerto Rico to capture some of the island’s remarkable sights. The #PuertoRicoNoFilter campaign encourages bloggers to produce unedited photographs of Puerto Rico’s natural beauty, because Puerto Rico is so picturesque it requires no filter…

Jessie Festa from Jessie on a Journey took on the challenge and also managed to explore some of San Juan’s historic must-dos.