Exploring San Juan, Puerto Rico

Brightly painted 16th and 17th century buildings loom over narrow cobblestone streets in the second-oldest European-established capital city in the Americas.  If in Europe all roads lead to Rome, in Viejo San Juan, all streets seem to end in the massive walls of old forts like El Morro, San Cristóbal, and  La Fortaleza.

Main Sights San Juan

But there’s more to the Puerto Rican capital’s old town than palm trees, Spanish fortresses and dangerously aggressive sunshine; you just have to keep your eyes open to find it. Wedged between the shops selling made-in-china souvenirs and assorted tourist traps, there are authentic restaurants serving traditional fare, unique accommodations and boutiques specializing in arts, crafts and accessories made on the island.

Authentic Eats

For the most part, food out is reasonably priced. But not all restaurants are created equal. The Old Town is crowded with tourist traps offering mediocre fare at inflated prices, but there are still plenty of good places to eat without leaving the area. One of my favorites, Café Puerto Rico offers authentic local cuisine, generous portions and well-priced lunch specials, but there’s always a wait at normal feeding times (12-2 and 6pm onwards). Be sure to try island specialties like shrimp soup (asopao de camarones, mofongo, and tostones. If you can plan ahead, you’re better off making a reservation. The conch salad at Mojitos is also quite good, even if the restaurant itself is dingy and poorly lit. For amazing fried chicken and fish, and tasty Caribbean classics in a hole-in-the-wall setting (plastic chairs, no AC, cash-only), try Fatty’s.

Unique Accommodations


At the end of the day, your hotel is home for the duration of your trip. Keep your downtime interesting by staying somewhere with more personality than your average Marriott or Sheraton. Beyond well-appointed rooms and fully equipped kitchens available for foodies and families, La Terraza Hotel San Juan has something I look for everywhere: a feeling of home. Staff are friendly and helpful, and the common spaces are clean and welcoming, with lots of charming details like mosaiced floors and hand-painted walls.

Charming Boutiques


Skip souvenir shops crowded with t-shirts and trinkets made in the P.R.C. You don’t really need an “I heart San Juan” t-shirt, not even for the gym, do you? Instead, search out boutiques specializing in arts, crafts and designs made in Puerto Rico. At Everything but Match, shop brightly colored original art, as well as clothing, toys and accessories from 26 Puerto Rican designers. Find hand-painted souvenirs at Mi Pequeño San Juan. For more jewelry and paintings made in San Juan and elsewhere on the island, another good choice, despite its rather uninspiring name, is Puerto Rican Arts & Crafts.

Bonus: Tips for first-timers

Beyond seeking out the hidden gems described above, here’s some expert advice for your time in the Puerto Rican capital.

1. Wear sunscreen. It doesn’t matter if you’re swarthier than a pirate, and never burn. The sun here is intense, and you don’t want permanent sun damage, or worse, a week of vacation photos featuring you and two of your best friends as reverse raccoons, slather up.

2. Buy a coconut from a street vendor. It’s an easy meal replacement. Drink the refreshing coconut water, then revisit your friendly vendor, and ask him pretty-please to slice it open for you so you can eat the coconut inside.

3. Fly a kite in the field in front of El Morro Fortress. It may be a super-touristy thing to do, but locals love it too, and there’s a reason why—it’s fun, and the views are hard to beat.


4. Embrace carbs for the duration of your trip. Give yourself cart blanche to enjoy plantains in all their variations, boiled cassava, rum cocktails and plenty of rice—you’ll be much happier.

5. Spend some time wandering—it’s free and you’ll find surprises around every corner. Art students lounge in plazas, drawing statues, fountains and each other. Locals leave out water and kibble in aluminum pie tins for stray cats near Ponce De Leon’s Casa Blanca. Saints pray and angels sing above street numbers on brightly colored colonial buildings. In front of El Morro, yellow school buses blare salsa and reggaeton as children in pale blue uniforms elbow their way on board. Murals and street art pay homage to Puerto Rican culture and local heroes like Ricardo Alegría.


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