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What Arriving In Puerto Rico Is Like

I’m back in Puerto Rico.

El Morro
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SAN JUAN- Those first rays of harsh sunlight and the blanket of heat that hits you when you first step outside of an airport in the tropics is one of the things that I love most in travel. For someone originally from Buffalo, it’s the one thing that makes you fully comprehend that you are somewhere else, somewhere far, far away from where you’re from. I like that feeling.

I followed the signs to the ride share area and called an Uber. As I was waiting I had to laugh at how easy getting away from airports is now. This used to be a mildly challenging travel move, depending on location. You used to have to either figure out the local bus system, how to pay for it, where to get off … or brave taxi drivers who, in many places, viewed incoming air passengers as dinner. Now you just push a couple buttons and chill in the sun for a minute. Peace. While you can no longer get lost, there are some things that are good about the smartphone era of travel …

My driver told me that his name was Jose, and it was clear that he wanted to talk. He was probably in his late 30s, wore sunglasses, and was a total dude. He told me that he was from the Rio Piedras part of San Juan and lived here his entire life. Although his mother was from the mainland and he had a lot of family scattered around there and expressed a love for Hollywood movies and various other vestiges of Americana, he didn’t really seem to have any interest in going there. He actually had never been. While people born here are full-fledged US citizens and can go anywhere in the United States or wherever a US passport can take them, most stay in Puerto Rico … and since the Covid pandemic net migration has ground down to almost zero. That means something.

I asked him what he thought was interesting about Puerto Rico. He told me to go to Old San Juan and visit the castles and ports and the beaches. He told me to go snorkeling, to just take long walks and check out the historic squares. He told me to eat mofongo and chuleta kan kan that has skin that’s cooked like a chicharron and go to the Placita de Santurce at night.

Old San Juan

It was the normal taxi driver recommendations but I jotted down some notes anyway. I’m not really one to do much research into the places I visit when just travel writing. I didn’t look up a single thing about Puerto Rico. Why would I when I can just show up and ask people who actually live there where they think I should go.

I was near the end of my ride with Jose and he told me the road was blocked ahead and that I would have to walk the rest of the way. I told him that I didn’t really care where he took me, as I just picked a random place in Old San Juan because I couldn’t check into my apartment until three and had nowhere else to go. He laughed and was like, “In that case you should go to El Morro. It’s the best place to start your travels in San Juan. Do you want me to take you?”

The first rule of travel: when someone offers to take you somewhere just say yes.

So we continued winding our way up to the castle that sits at the northwest point of Old San Juan. “This is good because it’s at the top of the hill so you don’t have to walk up it with your big backpack. Now you can just walk down,” he said as he let me out of the car.

The Castle of San Felipe del Morro was first built in 1539 — just 47 years after Columbus landed in the Bahamas — but took a couple hundred years to finish. It helped fend off various attackers during the subsequent centuries and in WWII the US actually recommissioned it for military purposes by using it as a station to track the movement of German submarines in the Caribbean. Today, it’s a historic site that tourists pay $10 to walk around. I found no need to go inside. Surrounding the fortress is a massive rolling grassy yard that people come to hang out and fly kites. The ocean laps against the shore to the north and the Bar Channel which leads to the Bay of San Juan is to the west. The sheer amount of public green space here is impressive, and I just hung out on the hill here for a while looking out at the sea and watching the people around me enjoy their days.

It really wasn’t a bad way to enter a city, but it was getting around 11 and I was starting to cook in the sun, so I went looking for a place to hang out in.

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The hours before check-in are one of the conundrums of modern travel. Check-out times used to be 11 am or noon, check-in times used to be noon or 1 pm. Now check-in times are 3 pm or even later. So what do you do if you change rooms or arrive early somewhere? Just walk around all day with your luggage like a dumbass? In the old days you used to just drop off your bags at your hotel or hostel and they would hold them for you until check-in time. But in this era of temporary apartment rentals and self-service hotels this really isn’t possible. I don’t have an answer here … and I spent my first six hours in San Juan trudging around with a Kelty 44 liter rucksack on my back and a shoulder bag with a Macbook in it on my front.

As I was walking away from El Morro I found exactly what I was looking for. It was a three-story bar called La Vergüenza that had open air patios on the top two floors that looked off over the cliff at the sea beyond. I looked up at it and was like, man, that would be a really good place to drink a beer. And I had nothing better to do.

View from la Verguenza bar

View from la Verguenza bar.

Jose actually pointed this place out as we drove by. “That’s a Puerto Rican chinchorro,” he said. “Chinchorro is a word that we normally we used to use when we are traveling in the countryside of the island. You go to the countryside and you start getting into the small towns and most of the roads are only two lanes and you’ll find yourself surrounded by a lot of green, you know, like trees and stuff, and you can go for like 20 minutes, 30 minutes until you find a spot where you can take a break stop or something. And you can order some food or drinks, listen to music, play table pool if you want. And those are chinchorros. And people on the weekends they say let’s go chinchorrear or chinchorriando (chinchorro-ing). That means that they are going to just hang out, you know.” 

I walked up to the second floor, took a table on the patio, and ordered a beer. I’ve probably only drank three beers in the past year. Beer is a travel-in-the-tropics kind of drink. There’s just something about the sun around the girdle of the global that makes you want to do little more than sit out in it with a nice cold beer.

Whenever I come to Puerto Rico I find it difficult to believe that I can just come here whenever I want and stay for as long as I want. Consciously, you know the official designation of the place, you know the history, you that there’s no immigration or customs protocols, no visas, no resident permits, or anything to indicate your foreign status, but for some reason you’re still not fully convinced. The place just seems a little too much like somewhere else — it’s its own place, and that’s what’s good about it.

Filed under: Puerto Rico, Travel Diary

About the Author:

I am the founder and editor of Vagabond Journey. I’ve been traveling the world since 1999, through 91 countries. I am the author of the book, Ghost Cities of China and have written for The Guardian, Forbes, Bloomberg, The Diplomat, the South China Morning Post, and other publications. has written 3706 posts on Vagabond Journey. Contact the author.

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VBJ is currently in: New York City

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  • Rob April 30, 2023, 5:11 pm

    I had a friend when I worked at the warehouse who was from Puerto Rico, he liked to ask if places took Puerto Rican money…it was fun!

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    • VBJ April 30, 2023, 7:21 pm

      Haha that’s funny!

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