Strolling Old San Juan’s Colorful Streets

Some of the most pleasurable parts of visiting a new place are free—as I learned while rambling among the vibrantly painted apartments and churches in Puerto Rico’s historic downtown area of Old San Juan. My entertainment during my two-day solo stay there was soaking up the atmosphere in Old San Juan, founded by Spanish colonists in 1521.

The streets of Old San Juan are a riot of Caribbean color. ©Laurel Kallenbach

The streets of Old San Juan are a riot of Caribbean color. ©Laurel Kallenbach

The architecture is a spicy mix of old-world Spanish and Caribbean tropical hues. When I got tired of walking, I stopped into some authentic local eateries to sample the flavors of the island too.

Yellow window, Old San Juan ©Laurel Kallenbach

Old San Juan ©Laurel Kallenbach

Old San Juan is probably Puerto Rico’s most-visited spot, and rightfully so, with its colonial, cobblestone streets lined by a rainbow of apartments with balconies and bougainvillea. Add in palm trees, fragrant food cooking at wonderful restaurants, and sweeping views of the Atlantic, and you’ll fall in love.

I did.

On my two days in Old San Juan, I wandered among the quieter boulevards and simply drank in the colors. Except for the cars parked all along the streets, it’s easy to imagine how the town looked in the 16th and 17th centuries, back when it was a Spanish colony.

Old San Juan has shops, of course. I dropped into a few local artisan shops during the quiet hours, early morning and late afternoon when the cruise ships weren’t in port.

The inner courtyard of private home. ©Laurel Kallenbach

The inner courtyard of private home. ©Laurel Kallenbach

There are also satisfying restaurants, including modest spots where locals grab breakfast or lunch. At Café Manolin, an Old San Juan institution that serves creole-style food, I had fried eggs and beans with tortillas while I watched the old-style orange juice machine mash up oranges and spit out fresh juice. It tasted heavenly.

For high-end dining, there are many possibilities in the old town. One evening I enjoyed an early dinner at the snazzy Hotel El Convento tapas bar, where I sat on the patio overlooking the courtyard. Contentedly, I sipped a Bacardi Mojito and savored slices of Manchego cheese drizzled with truffle honey served with fresh-baked bread.

Mostly though, I wandered Old San Juan until my feet were sore or I got too hot in the Caribbean sun. That’s when I knew it was time to return to my “home” during my stay: the Casablanca Hotel. There I could nurse a margarita or cold Puerto Rican cerveza—the Old Harbor Taina brews are lovely—and watch one of my favorite movies of all time projected on the wall of the bar. Or, I walked up the stairs for a siesta in my room, which was small but comfy with a Moroccan flair.

I never got tired of taking photos of the brilliant architecture. ©Laurel Kallenbach

I never got tired of taking photos of the brilliant architecture. ©Laurel Kallenbach

The concierge at the Casablanca steered me to the best restaurants, and he humored me by letting me practice my Spanish. (For the record, most puertorriqueños speak fluent English.) This U.S. territory uses the American dollar. And I did a double-take one day when I bumped into the mailman wearing the traditional U.S. mail uniform—with shorts of course!

In addition, the Castillo San Cristóbal fortress and the Castillo San Felipe del Morro  are part of the U.S. National Park Service, where interpreters in those Smoky Bear hats give you guided tours of the old fort walls overlooking the azure ocean.

Mostly I loved Old San Juan’s small details, like iron knockers, glimpses into courtyards of apartment buildings, and colorful shutters. Nearly every apartment number was painted on glazed tiles.

Pink lantern, Old San Juan ©Laurel Kallenbach

Pink lantern, Old San Juan ©Laurel Kallenbach

One morning, after breakfast, I was crossing a plaza and saw a skinny, feral cat dash out of nowhere and grab a pigeon from a flock pecking at the cobblestones. I was shocked; domesticated cats back home are rarely that fast, but clearly this cat was hunting for his breakfast!

A few hours later, I noticed a grumpy Persian perched inside the window of a posh apartment. He gazed out at the street with a pout that reminded me of a grounded teenager.

No, pampered puss, you have an easy life in your house, I thought. The streets of Old San Juan are lovely for us tourists, but they would be hard for a cat like you.

Brass knocker on a door ©Laurel Kallenbach

Brass knocker on a door ©Laurel Kallenbach

On and on I strolled the quiet streets of colonial San Juan, enjoying the arched entryways, elegant shuttered windows, and ornate iron grillwork—an art form brought to the New World by the Spanish.

Viva Viejo San Juan—viva Old San Juan!

Laurel Kallenbach, freelance writer and editor

Read more about my travels in Puerto Rico: