Twilight in Old San Juan


By Alexander Britell

OLD SAN JUAN — “Take me to Fortaleza.”

“No, take me to El Convento,” I tell the driver instead.

With rum in the future, I figure it’s better to start higher up in the hills of Old San Juan.

Rum is always better downhill.

“Here’s OK,” I tell him, getting out in front of Ostra Cosa on the San Sebastián Strip, home to, most famously, El Patio de Sam, the onetime hangout of San Juan sojourners like Hunter S. Thompson.


It’s known as a burger joint but it also serves some of the city’s best mofongo and some of its best chicharrones. Okay, so some of the best everything. But that’s true of most places that last 70 years.


San Juan is a different city than most in the Caribbean. It’s a place for walking, a place that gets more interesting by night, not more quiet. And San Juan at dark is a different place than it is by day.

In the morning, it’s a colorful jewel box of a city, great for tourist snapshots and hidden cafés, vibrant and smiling.


Just after twilight, when the sun dims, you can hear your own footsteps on the cobblestones, and new lights emerge out of the doorways. You see the locals watching you out of their second floor windows, and then a family opens their front door to sell tres leches to passers by as they watch TV.

Under the yellow lamps, the watering holes emerge and you hear the domino games begin.


Rum is always better downhill.”


Many streets are empty, just me and my footsteps, but many are bustling, the couples out on the town and the mainlanders who stayed around, everyone exploring.

It’s on the early side, so the tapas place is quiet. So is El Patio de Sam.


So I keep walking until I find La Mala Vida, a Mexican tavern. How can I not try a place called that.

It’s getting crowded, and I order a Barrilito and watch the people come in. (Yes, I like Barrilito, but if you want to taste real Puerto Rican rum you drink this.)

It’s a bit ironic that a 500-year-old city is one of he most energetic places in a region full of mostly 30-something countries.

The more I walk the more I find another old building revivified, serving tapas or Italian food or pastelitos or a contemporary Mexican cantina.


There’s a beat here. The people on the streets walk to a metronome, knowing the right rhythm to start their night.

That’s before the hours fade and the beat turns to jazz.


Above: espresso at Cuatro Sombras

In an old place, restoration and renewal give off heat and light. And you feel it as you walk.

And that’s the only way you know a city. Feeling it with your steps.

On empty streets it’s just the two of us, Old San Juan and I, in constant conversation.


I step and step and she tells me to turn. I walk on the left and then something tells me to cross, or when it seems someone else wants to chime in.

A man and a woman are closing their apartment door and getting ready for dinner. There’s a loud radio in a small bar with the Medalla Light sign.

There are the old San Juaneros on the benches in the plaza, remembering earlier nights and staring at the brightly-lit walls of the student center.

I walk and walk, down the hills and back up again.


The bars begin to fill up, and there’s more music.

I walk past Da House, the onetime artists’ collective that’s now a Posada, or boutique hotel.

It’s on the second floor of a building that houses the Nuyorican Cafe.

“Live music at the Nuyorican Cafe!” The promoter shouts, behind the just-laid ropes.


I’m hungry, though, and I keep walking.

I descend to the flat part of the city, and stop for an espresso at Cuatro Sombras, a high-quality cafe serving Puerto Rico’s famous coffee. (The Pope used to drink it, in nicer cups).

Then I pick a place at random, and find Inarú, an artisan Puerto Rican restaurant in a deep building with high ceilings.

There’s a seat at the bar, I order rum, a sampler and mofongo with churrasco. Because it’s hard not to order mofongo when you’re here.


The meal is good. Simple.

So I leave and explore more.

I walk up Fortaleza, past the cigar lounges, past the street musicians, stopping to check out Rick’s Café, downstairs at the Casablanca Hotel. There are those high ceilings and it does feel a bit like Morocco.


Calle Fortaleza is getting more crowded, the sidewalks a little narrower.

I spot a cab, then another. San Juan is just waking up.

And then I start walking again.