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What’s New in Old San Juan

View from El Morro. Photo Deborah Gaines.

By Deborah Gaines

Like most of us, I have a travel bucket list. I crave exotic destinations, electrifying experiences, and adventures I’ll never forget.

But after three years of pandemic restrictions, I’ve lost my appetite for discomfort. I’m not willing to take the kind of risks that once invigorated me, at least for now.

Enter Puerto Rico. This United States territory shares citizenship (no passport required), currency, and electrical frequency with the mainland. You won’t need a travel plan for your cellphone or an international ATM card.

Yet the island’s beauty and history are as compelling as the most far-flung countries on my bucket list.

Let’s start with Viejo (Old) San Juan. Since we only had a few days, we flew nonstop from Newark (choose from Delta, JetBlue, Spirit, or United) and took a twenty-minute Uber ride ($25) to the heart of the historic district. From here, everything was walkable, including museums and attractions, restaurants, and a peaceful local beach.


The lobby of El Convento. Photo Deborah Gaines.

Where to Stay

For the price of a four-star hotel room in nearby Condado, we stayed at a spacious, two-bedroom Airbnb on Calle Sol. Other options in the historic district include the charming Decanter Hotel (rooms start at $270, less in the off-season), across the street from the Catedral de San Juan Bautista, and the similarly priced Hotel Palacio Provincial, whose small rooftop infinity pool offers views of the historic harbor. (A third boutique hotel, El Convento, has a leafy courtyard where you can enjoy lunch or dinner but may be noisy at night.) A short taxi ride away, the Olive Boutique Hotel is a special-occasion splurge, with views of the Condado Lagoon and spacious suites starting at around $400/night in the winter season.


Paseo del Morro. Photo Deborah Gaines.

VSJ in a Day 

If you’re docking in San Juan during a cruise, or stopping by on your way to a beach resort, here are three attractions you won’t want to miss:

Paseo del Morro. This mile-long, pedestrian pathway starts at the City Gate, the last remaining vestige of the Spanish Colonial era, and winds along the harbor for nearly a mile to the Castillo San Felipe del Morro. (You can also access it from the Paseo de la Princesa, very close to the cruise port.) Every step offers million-dollar views of the soaring fortifications to your right, and the sapphire-blue sea to your left.


La Fortaleza. Photo Deborah Gaines.

The paved walkway dead-ends beneath the famous fort, but if you have the energy, climb the steep staircase and follow a smaller path for an astonishing view of the Atlantic Ocean and Old San Juan Cemetery. 

Colonial Architecture. The compact historic district boasts more than 400 restored Colonial-style buildings in a rainbow of bright colors, so wandering is a must. And don’t forget to look down: the streets are paved with silver-blue cobblestones, called adoquines, made from the waste created by iron smelting and transported to the New World as ballast in the holds of 18th century ships. Stop by the oldest cathedral in the United States, San Juan Batista, and pay $2 to wander around inside. Or tour the governor’s residence, La Fortaleza, weekdays from 9 to 3. 


Pastries at Spiga. Photo Deborah Gaines.


Boricua cuisine. Maybe it was the rum (try the Trigo Reserva Gran Añejo or the newer Ron Coquí) or the local beer, Medalla, but I do not recall a single bad meal from my time in Viejo San Juan. Mornings began with coffee and fresh-baked pastries from Spiga, downtown near the cruise port, while lunch featured mofongo (mashed plantains) with pork crackling, pernil (roast pork) or garlic-drenched seafood, and amarillos (sweet plantains). Don’t miss the sampler platter at hole-in-the-wall Deaverdura on Calle Sol—there’s a reason the line snakes around the block. If you can’t wait, San Germain Cafe offers sandwiches and wraps in a refined setting across the street.


Playa Pena. Photo Deborah Gaines.

Time to Relax

While it’s possible to sample the city’s charm in a few hours, Viejo San Juan improves on longer acquaintance. Late afternoon was my favorite time, as the sun grew more forgiving and the crowds dispersed.

Each day, we walked past the Castillo San Cristóbal to the small beach at Playa Peña, across the street from the Capitol Building, where we could wave to departing cruise ships as we floated in the warm water. Our evenings began at Carli’s with live jazz and “the world’s best mojito” (or pretty darn close), and ended at La Verguenza, a rooftop bar with a DJ on weekends and stunning harbor views.


Carli’s Mojito. Photo Deborah Gaines.


Other standouts included the Farmer’s Market in the courtyard of the Museo de San Juan (Saturdays from 8 a.m. to noon), where I discovered kombucha made from local fruit; lunch on the patio at El Convento; and craft cocktails at La Factoria, one of the “World’s 50 Best Bars.” We also enjoyed shopping at the Poet’s Passage, as well as the stores along Calle Fortaleza, and scored some outstanding coffee to take home at the Supermax on Calle de la Cruz.

Best of all, I returned after five mostly unstructured days feeling rested and relaxed—as though I’d been on vacation. As I sip my mug of strong, fragrant Draco Rosa or Cafe Loreno, I’m already plotting my return.


Deborah Gaines is an author and travel writer whose work appears in Huffington Post, Salon, and American Lawyer, among others. Follow her on Instagram @deborahgaineswriter

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