Finding the local watering holes

A peek at La Placita in San Juan on a Saturday night

From the quiet, residential looks of the streets, you might get the impression that you’ve wandered too far from the beaten path.

The narrow streets that barely fit one car but somehow fit two, take odd turns and pivots in the lane ahead. As you pass each home, you nod politely a the neighbors sitting out on their stoops, Medalla beers in hand, trying not to attract too much attention, as you keep on your way. Maybe you’re a bit further than you’d prefer from the beach and hotel-lined avenue where you’ve spent most of your time to date. But it’s good to push yourself a little outside your comfort zone, you remind yourself. That’s why we travel. Besides, the blue dot on your Google Maps tells you it’s still another three blocks to go, and yes, you do have to walk underneath the highway overpass to get there.

This might be the point when you might think twice about continuing on. You may feel the teensiest of bristles on the back of your neck as your inner voice asks, “Is this okay? Are you? Shouldn’t we go back?”

This is one of those times when you should ignore that voice.

That’s not to say it’s wrong — it’s just doing its job, of course. But sometimes (and particularly when traveling somewhere new), I’ve found that my voice has two types of inner flags. There’s: “Whoa, watch out! This is different!” and then there’s: “Uh oh…This feels downright dangerous.”

The former is okay; that’s how we grow and learn. And it’s only natural for our internal, running monologue to freeze up a bit when we encounter a situation or environment that’s foreign to us. Pushing through this concern is how we grow and learn and build empathy with new people and places. But the latter — that’s the scary stuff. Most of the time, when you hear that voice, you probably do want to listen.

Of course that’s the tricky part about traveling; finding your way in with limited time and local know-how and pushing just at the edges of your own comfort zone to find it.

If you do manage to quell that inner voice and push on to your destination — an unmarked restaurant named Jose Enrique that a friend of yours told you about — the payoff will be great. You just may have the best meal of your trip, sit at the bar alone, and befriend the person next to you who randomly shares a bit more in common with you than you would have thought.

And that’s how you’ll get introduced to La Placita — the local watering hole just around the corner, where Puerto Ricans promenade all night long, listen to live music, enjoy tostones outside, and smoke oaky cigars in the streets.

I was lucky enough to be toured around this magical corner of San Juan three years ago, on my last solo adventure here. Now, three years later, I came back, this time with my husband and a few friends. It felt like letting everyone in on a little, local secret.

The best part about La Placita is that it feels like an in-the-know-only oasis, just blocks from the main drag of hotels, bars, and restaurants along the beach. Yes, you do have to trust the system enough to wander there to begin with. But once you do, you’ll feel closer to the community than any other moment of your trip.

My favorite way to experience a new place is to stay there long enough to be able to see it from a local’s point of view — to be a part of their excitement, their frustrations, and their tedium. This is often easier said than done (particularly on short trips), but if I can get a few pointers in the right direction from people who live in the area, I always try.

It’s a rare treat to glimpse a typical day from the vantage point of someone else completely unlike yourself. So if you do manage to stumble upon a local watering hole, be sure to thank whoever introduced you to that place. Just be sure to pay it forward the next time you meet a wayward traveler in your neighborhood.

GM @USV, alum of @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store