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Traveling to San Juan in 2019: What I Learned

January 29, 2019

My name is Sam, and I’m ViaHero’s Senior Content Manager. Two weeks ago, I spent 3 days exploring San Juan. That’s 14 months since Hurricane Maria, if you’re counting. These were my takeaways.

*Note: The opinions expressed in this article are solely those of the author, and do not necessarily represent the opinions of ViaHero LLC.

I thought I could wing it. I thought wrong.

I work for a company that literally plans trips to Puerto Rico, so I know how dumb this sounds—but I didn’t actually prep for my trip. Pride, stupidity, smug laziness (cough), call it what you will. The point is, I’ve been knee-deep in research on Puerto Rican tourism for the past three months, so I thought I could just wing it. I was wrong.

Ok, ok—in my defense, I’d only bought my tickets a couple days before my trip, and I didn’t want to beg one of our Heroes to make me a super-expedited guidebook and itinerary. I thought I’d be fine with a (shudder) Lonely Planet and (double shudder) TripAdvisor.

Honestly, I’m glad I had the Lonely Planet. I used it to make sure I didn’t miss any major sites when I was exploring Old San Juan, though it didn’t give me much in the way of non-touristy restaurants or things to see. 

TripAdvisor was a bit more hit-and-miss. On my last day in town, I used it to try and find a good beach for bodysurfing. I ended up at a beach where speedo-clad elderly gentlemen go to swim laps and do Tai Chi. Not too many waves, as you might imagine. So, you know. TripAdvisor.

Sam ViaHero San Juan Travel...
Me, San Juan, an $8 selfie stick.

Anyway, I got super lucky—my Airbnb host (shoutout Casey) gave me a ton of recommendations that turned out to be fantastic. Plus, I got a lot of great advice from locals I met in passing. Some highlights:

  • A ‘50s-style diner hidden away in the most touristy part of Old San Juan, jammed with elderly Puerto Ricans, serving the best mofongo/Puerto Rican comfort food I’ve ever had.
  • A fantastically scummy dive bar where San Juan’s hipster elite gather to shoot rum, drink cheap beer, and play pool (Benicio del Toro was apparently there the night before I was).
  • A cafe called “Empanadas and Birra” (best empanadas I’ve ever had) that’s not even on Google Maps. Que exclusivo.

Ironically, getting local recommendations for travelers is the entire point of the company I work for, which makes me even more of a dumb-dumb for trying to wing my trip. At one point I got dangerously close to eating an $18 hamburger at a place that claims to have invented the piña colada (spoiler: they did not invent the piña colada). My heart cried a single tear. I opted for questionable street meat instead.  

Old San Juan is full of tourists… but weirdly, they all seem to be Puerto Rican

Old San Juan, which is essentially just a gorgeous and perfectly-preserved colonial village (I’ve got a lot to say about that in a second) is packed with tourists. The weird thing? They all seem to be Puerto Rican.

The couples walking down the street looking through guidebooks? Speaking Spanish. The families taking selfies in front of monuments? Chatting in Spanish. The groups of 20- and 30-somethings bar-hopping in über-fashionable getups? Drunkenly crying in… you guessed it. Spanish.

Obviously, I assumed they were Spanish-speakers from other parts of the world. But the Sanjuaneros I chatted with (shoutout Pablo—if you’re reading this, you were 100% right about Piñones) told me otherwise. Apparently, Old San Juan is just the place to be. During the day, people come from all over to see the sights. At night, they come to see and be seen.

Case and point: I did a fair bit of bar crawling on Saturday night—I was traveling solo, what can I say—and almost everyone I chatted with told me the same. And while Ubering out of Old San Juan, my driver (shoutout Luis; he’s going to make a dramatic reappearance later in this article) pointed out that the traffic going back into the old city was gridlocked. On a Sunday night!

Anyway, did I see other tourists? Sure. Mainland Americans, East Asians, Western Europeans, even some Brazilians. But by and large, even with the cruise ships in town, almost all the tourists I saw were other Puerto Ricans.

Sanjuaneros are SO freaking cool

Ok, this is obviously a massive generalization, and I realize the cross-section of people I met is extremely limited. But regardless, the Sanjuaneros (people from San Juan) I hung out with were so. freaking. rad. First of all, everyone is at least somewhat bilingual—I speak a bit of Spanish, but I never had to use it.

And everyone is interesting. Music, politics, travel—it seemed like everyone I chatted with had something cool and genuine to talk about. Again, I live in Brooklyn. And in Brooklyn, everyone you meet wants to talk about their shtick. Their probably-nonexistent band. Their fake knowledge of Russian literature. Their plans to become a “digital marketing influencer”. You know, their schtick. This wasn’t that.

And everyone dresses really well. The seemingly-effortless hipster-chic fashion in San Juan puts Brooklyn’s to shame. And it’s not just the millennials either. Everyone from the elderly ladies dancing in La Placita to the teenagers drinking beer in La Perla—after sundown, everyone's dressed to the nines.

And most importantly: everyone is warm. People on the street wave and say hello. Strangers strike up conversations in bars. People buy you drinks when they find out you *cough* strongly dislike certain political figures. Sixty-something-year-old Uber drivers quit for the night so they can spend six hours drinking with you in Piñones.

Oh yeah, that happened. See? I told you Luis was going to make a dramatic reappearance. Seriously, when he heard I was just dropping my bag at the airport before going to have dinner in Piñones (and if you don’t know about Piñones, read up on it here), Luis told me that a: I shouldn’t go there after dark and that b: if I was set on going, he’d wait for me at the airport and take me there himself. We ended up drinking beer, listening to music, and eating alcapurrias until after midnight.

Turns out, Luis is a wine lover and regularly travels to Napa Valley. Oh, and he’s even been to Santa Rosa (where my grandparents live), and “cried for the city” when part of it burned in a wildfire last year. Luis is amazing. If you’re looking for someone to drive you around Puerto Rico, his information is at the bottom of this article. And that brings me to my next takeaway, which is this:

Everyone parties

So I’m a pretty outgoing guy. I’ve been called “muppet-like” more than once. Some have even gone so far as to label me “a man of the people” (thanks mom). The point is, I don’t have any problem traveling solo. I like going to bars by myself. More often than not, I end up making friends and having a great time. Which is why I assumed I’d just spend Friday and Saturday night moseying around La Placita de Santurce, having some quiet drinks, and chatting with some Puerto Ricans.


Apparently, there’s no such thing as a quiet drink at La Placita—or anywhere else in Santurce for that matter. Because everyone is partying. By 6 or 7, the place is packed. And not just with 20-somethings. From teenagers to retirees, everyone is dressed up, drinks in hand, shouting over the music pumping from every bar around. Middle-aged moms drunkenly salsa together while their husbands cheer. Groups of 18-year-olds giggle and crush cans of Medalla. Grey-haired bankers loosen their ties, slap each other on the back, and shoot rum. It’s glorious.

I ended up finding my quiet bars, but they were more in Old San Juan than Santurce (though I did find a couple there too). I met a lot of incredible people as well (see the shoutouts above). But my advice: if you’re not planning on getting crazy, you should probably try and get some recommendations before you head into town.

San Juan is totally back to normal, but the hurricane damage is there if you know where to look

I explored greater San Juan for three days, and for the most part I was (no pun intended) blown away by how normal everything seemed. I mean, our Heroes have been telling me that for months, but I read the news. There are still stories about how PR is struggling, PR is still rebuilding, the economy is in free-fall, etc. Honestly, I didn’t really see much of that. That's not to say the stories aren't true—in fact, I'm 100% sure they are—but in San Juan, it's hard to tell.

See, Old San Juan is manicured. I mean seriously—it’s pristine. There are cops everywhere, it’s perfectly restored and painted, the place is idyllic. I know that’s largely due to concerted government tourism efforts, but still. Even in Santurce, Miramar, and Rio Piedras, places that aren’t known for their pristine exteriors, everything looks... normal.

In Old San Juan, I would say that out of every 50 buildings I passed, only one or two were still abandoned or under construction. That number was a little higher in the rest of the city. There, I’d put the number of blown-out buildings at… maybe one in every 25 or so. There were a couple abandoned office buildings in Puerta del Tierra that I saw from the highway as well—but honestly, if I hadn’t known about the storm, I would never have guessed anything had happened.

Plus, I grew up in Oakland and I live in South Brooklyn (Lefferts-Flatbush represent), so an abandoned building every block or two just seems normal. Not in a weird way, I don’t live in a bad neighborhood or anything—it’s just what you see in any big city. What I’m trying to say is that I only noticed the damage because I was looking for it. The only area where that wasn’t the case was La Perla.

La Perla is jarring, but important to see

If you don’t know what La Perla is, it’s the only low-income area of Old San Juan. And technically speaking, it’s not really in Old San Juan either; it’s perched on the outside of the old city wall itself, zigzagging its way down the cliffside all the way to the ocean. To get there, you take one of the driveways or staircases that drop through the wall from the northern edge of Old San Juan.

And let me tell you, that 2-minute walk down to La Perla is jarring. I was serious when I said San Juan is manicured. La Perla isn't. While Old San Juan is full of tastefully-finished hoity-toity Spanish Colonials, La Perla is full of flamboyantly-painted concrete shanties. Most are two stories, some with businesses on the ground floor. The first thing I saw when I entered: a pair of stray cats asleep in front of an open-air bar, while a hen and three chicks strutted by. It’s like going from Stepford to South Bronx in the space of 100 yards.

Actually, that’s not really a fair comparison. I never felt unsafe in La Perla. Aside from the three teenagers who jogged up, smiling, to offer me identical selections of drugs out of identical pencil boxes (Stringer Bell would have something to say about that miscarriage of free-market capitalism), I didn’t see anything remotely sketchy. Granted, it was just after 2 PM, but the fact remains. To me, La Perla just seemed like a cute—if rural—Caribbean village.

Jarring contrast from Old San Juan aside, La Perla definitely gave me a more rounded view of how Puerto Rico is actually recovering from the hurricane. I only walked through the upper terraces of La Perla, but even there, the roads are still broken up. Every sixth building or so is blown out. Some abandoned buildings have tents on the roofs, some have bars operating below the rubble. Here’s the part of town that hasn’t really recovered.

Like I said, to the casual traveler (me) the rest of San Juan seems almost completely back to normal. But La Perla shows you how the neediest in Puerto Rico live, and they’re clearly still reeling from Maria. I'd venture a guess that much of the rural countryside is too. And since most travelers to Puerto Rico will never see that, I'd say La Perla is well worth a visit—even if just for a few minutes.

That said, everyone was warm. A bunch of guys drinking beer at an outdoor bar waved me over to ask where I was from—and then promptly bought me a beer. A woman sweeping her stoop smiled and yelled: “welcome to La Perla!” Everyone was nice. Puerto Rico, man.

San Juan is like Havana on capitalism

That brings me to my next point: for better and worse, San Juan is like Havana on capitalism.

Unlike Havana, which absolutely envelopes you with its exoticism from the moment you arrive, San Juan is meant to feel familiar. Traveler-heavy areas (including the airport) are meticulously overseen by the Puerto Rico Tourism Company. The taxi trip from airport to town is carefully regulated. There are tourism information kiosks everywhere. Havana has a specific smell—diesel, refuse, and cigars—whereas San Juan smells like the ocean. San Juan’s cars are new, and there’s traffic on the highways. Old Town is, like I said, pristine. You don’t see horse-drawn produce carts. People speak English. Nobody's trying to hawk bootleg cigars out of a backpack.

And San Juan’s neighborhoods are distinctly un-Cuban—starkly differentiated by economic class and, as I found out, gentrification. I saw a sizeable homeless population, which I’ve since learned is due in no small part to the "excellent emergency management" recently provided by FEMA. There are drugs. There's crime, though mostly just petty theft. There's McDonalds's.

But those downsides come with perks too. You can use Uber! There’s internet! The landmarks are well-preserved! You can drink the water! You don’t have to eat government cheese! Like my grandfather always says, “there’s no free lunches”.

Anyway, I know this speaks to my privilege—but as a traveler, I would say the worst part of San Juan’s "Americanization" (yeah, yeah, you know what I mean) was the difficulty I had finding authentic spots to eat and drink in Old San Juan. Those places still exist, but like I said earlier—they’re hidden within layers of tourist crap.

Everyone speaks English

As our locals have told me again and again, “everyone speaks English”. Turns out, they’re not wrong. Of all the people I spoke to (and again, I spoke to more people than I should’ve), only one woman didn’t speak English—and that’s because she was from the mountains and had only come to San Juan to sell her delicious coconut candies. She sets up on Paseo de la Princesa every weekend, go buy her stuff.

The water is fine to drink

Again, our Heroes have told me over and over that the water is fine to drink—but given all the articles that’ve come out about Puerto Rico’s water since the hurricane, we’ve always described it in our content as “questionable”. Well, I drank the water (and a lot of it), and I had no problems at all.

Basically, it was amazing

Go to Puerto Rico. Seriously, it was absolutely phenomenal and probably the easiest trip I’ve ever taken. If you have any questions about traveling to PR, here’s our Puerto Rico FAQ sheet. You can also send us a message for more information, or jump right in and choose a local to plan your trip. Vaya con Dios, my friends.

Oh, and as promised, here's Luis' info:

Luis Wiso Vélez | wisovelez@hotmail.com | (787) 662-8556

And a couple more resources if you’re interested:


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