Bienvenido a Viejo San Juan

How could you not love a city that looks like this?

Early morning in the streets of Old San Juan (photo credit: canuckrunningamuck)

Homes in soft neutral tones in Old San Juan (photo credit: canuckrunningamuck)

Old San Juan was our first destination in Puerto Rico, the perfect introduction (or in my case, reintroduction) to the island. This historic district is crisscrossed by cobbled streets lined with Spanish colonial buildings in vibrant pastel hues. It is, naturally, a must-see for anyone who visits, but especially for those who love architecture, photography, or a killer backdrop for Instagram fashion shoots.

Old San Juan is filled with photo opportunities (photo credit: canuckrunningamuck)
Seek shade under the beautiful old trees (photo credit: canuckrunningamuck)

The imposing Spanish Fort of San Felipe Del Morro looms over the city on its western side. It commands views of both San Juan and the harbour, and it is the perfect starting point to develop an understanding of Puerto Rico’s colonial history. There is a small entrance fee for the fort, but this helps to support ongoing restoration projects. (It is free to wander the expanse of grass and the portion of the wall in front of it.) It takes about half a day to do the whole fort, and is best done in the morning before it gets too crowded.

View of El Morro at night (photo credit: canuckrunningamuck)

From El Morro’s walls near the main entrance, you can peer down onto Santa Maria Magdalena de Pazzis Cemetery, situated between the fort and La Perla, San Juan’s colourful but not-exactly-visitor-friendly slum. If you have time to wander through the cemetery, you’ll encounter graves of some of Puerto Rico’s most prominent figures.

Santa Maria Magdalena de Pazzis Cemetery, as seen from the walls of El Morro, with San Cristobal tower in the background (photo credit: canuckrunningamuck)

After that, wind your way down the blue cobblestone streets, towards El Paseo De La Princesa. This sweeping promenade follows the curve of the fort’s walls, right along the water. The old trees have huge swaying branches, providing blessed relief from the sun; look up, and you might even catch sight of an elusive Puerto Rican parrot. As you might imagine, these birds are found only on this island.

El Paseo de la Princesa (photo credit: canuckrunningamuck)

The Paseo also takes you by the old gateway to San Juan, once the only way into and out of the city on the water’s side. Informative placards posted at intervals along the walkway provide history in small bits. And you might just catch some local iguanas sunning themselves on the rocks.

The view of El Morro from El Paseo de la Princesa (photo credit: canuckrunningamuck)

Truly, the best way to experience Old San Juan is with your own two feet. We strolled down side alleys, climbed narrow staircases, popped into a cafe to get out of the heat and cool down with a passion fruit and papaya smoothie. (Pina coladas are also an appropriate option.)


Street view from Old San Juan (photo credit: canuckrunningamuck)
Old San Juan is famous for its blue cobblestones (photo credit: canuckrunningamuck)

Museo de las Americas is an architecturally intriguing building a few steps away from El Morro. An art museum by day, it transforms at night into a beautifully illuminated courtyard with a restaurant or two to stop in. Bonus: if you sit outside the Cinema Bar, you are treated to views of the fort lit up in all its glory.

The museo’s courtyard, illuminated at night (photo credit: canuckrunningamuck)
El Morro by night (photo credit: canuckrunningamuck)

There is plenty to see outside of Old San Juan, too. It is a quick ride by car to the districts of Condado and Santurce, both of which have their own unique, and distinctly separate, character.

Condado’s beach (photo credit: canuckrunningamuck)

Condado is vibrant, full of upscale bars, restaurants, and shops. Its sweeping beachfront is perfect for a pre- or post-meal stroll, and there are a number of quirky boutiques and cafes to poke your head into. Our favourite was SOBAO, a bakery with an industrial aesthetic and plenty of plants hanging in its airy space. (Ask a local, and they’ll tell you there’s also a “secret” restaurant in the back of the building, accessible through what looks like a freezer door.) But there’s no need to limit yourself to a tried and tested place. You have your pick of cuisines on Ashford Avenue, the main thoroughfare that runs through Condado.

The interior of SOBAO (photo credit: canuckrunningamuck)

Santurce, a walkable distance from Condado, is cool in its own, completely different, way. Having once carried a less-than-savoury reputation, parts of Santurce are now transforming into a uncommon, hidden find. There is amazing street art, a communal book exchange, a hopping breakfast place (Pinky’s), and a barbershop-turned-bar (fittingly named El Bar Bero), to begin with. Santurce’s character is grittier and less glamorous than Condado’s, but its brassy energy is contagious.


El Bar Bero, a barbershop-turned-bar (photo credit: canuckrunningamuck)

If you want nightlife that’s a little different from the tourist experience, La Placita in Santurce is the place to go. It’s a burgeoning hot spot for locals, where the market square transforms at night into a maze of bars and restaurants. There is always music, always dancing, and the party goes all night. Revelers often spill out from the clubs into the streets; be prepared for rowdy crowds and live music. Even better, grab a mojito and join in!

Even if partying isn’t your thing, La Placita is worth visiting, if only to sample some local cuisine. Cocina Abierta serves up delectable traditional food, with savoury Puerto Rican favourites like carne guisado and mofongo, fresh, locally-caught fish, and hearty classics with a twist. Their menu is seasonal and changes regularly, ensuring there’s always something new to try.

San Juan is gorgeous at sunrise or sunset. It offers a tantalizing taste of Puerto Rico’s beauty, and left us longing to see more of la isla del encanto!


Street views of Old San Juan (photo credit: canuckrunningamuck)

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