Meeting Peter
I stood on a hill overlooking the Atlantic coast and La Perla, a coastal shanty town the internet had warned me about. As I turned inland to scan the high rises for my Airbnb, a shaggy, bearded man poked his head over a nearby rooftop and proceeded to lower a set of keys attached to a thin yellow rope. Without so much as exchanging a word, I untied the keys, opened the door to the building and made my way up to the top floor.
The apartment was technically as advertised: a modest, one-bedroom unit comprised of a living room, kitchen nook, bathroom and private terrace that faced the ocean and the northern stretch of San Juan. As the majority of the online reviews put it, the space was rough around the edges with clear signs of where Hurricane Maria had taken its toll, but between the vibrant furnishings and tiled walls and floors, there was an old-school Spanish charm to the place that more than compensated for the rest of the apartment’s ‘quirks’.
Peter, aforementioned bearded man and also my host, looked to be in his late-60s. With his matted grey hair pulled into a messy bun, paint-covered khakis and dirty fingernails, he looked what I could only describe as an aged yoga practitioner who did acrylic murals in his pastime. Turns out he was a Jersey-born, practicing attorney who had been living in Puerto Rico for over 30 years, currently residing in Old San Juan with his wife and daughter.
On Old San Juan
Viejo (meaning “Old”) San Juan—the area that I would call home for the next week—is dubbed the historic district of San Juan, the capital city of Puerto Rico. Puerto Rico’s Spanish roots could be seen in the area’s Gothic architecture, open plazas, cobble-stoned streets and colorful apartment buildings embellished with white balconies and hanging foliage.
The combination of its aesthetic, walkability and historical significance make the neighborhood one of the most popular among tourists, who gathered into hoards of floral prints and khaki polo combos on seemingly every street corner. In addition to the presence of Marshall’s and KFC outlets, even the bars and restaurants were notably tourist-catered, offering Westernized cuisine and a strangely-consistent presence of late-90s British rock. My first meal, for instance, was at a grungy dive bar that solely served reheated empanadas, which I happily ate to the entirety of Pink Floyd’s The Dark Side of the Moon.
Inner Turmoil
Perhaps more distinctive to Old San Juan are the San Felipe del Morro and San Cristóbal forts, two Spanish-built fortresses over 400 years old. As I would come to learn, Puerto Rico originally belonged to the indigenous Taíno people, but its discovery by Christopher Columbus marked the beginning of several centuries under Spanish rule, under which it served as a critical military powerhouse given its strategic placement within the West Indies. It was finally taken over by the U.S. in 1898 following the close of the Spanish-American War.
From my conversations with residents, it quickly became clear that this historical theme of colonization and exploitation was very much ingrained in the island’s modern identity. While considered a U.S. territory, Puerto Rico is neither a U.S. state nor an independent nation; instead, it’s a ‘commonwealth’—an ambiguous title that leaves plenty of room for question around its residents’ actual rights and sovereignty. For example, in spite of holding U.S. citizenship and falling under federal jurisdiction, Puerto Ricans have no representation in the House or Senate.
Amidst this historical and geopolitical backdrop, Puerto Rico has been in crisis mode for the past few years, facing a long-standing recession fueled by accumulated debt, natural disasters, a population exodus and a governmental mismanagement of funds, among other things. During the second night of my trip, a local bartender explained the ongoing, localized corruption that occurred on a daily basis.
“Here, it’s all about who you know, from your everyday social circle right up to the government officials. So say $1M is borrowed by the government to rebuild a school destroyed by the hurricane. The person appointed to lead the project then begins building the school’s infrastructure, but gives $700,000 of the money to ‘paint a mural’ for the school because he is a friend of the artist. Of course at that point there’s not enough money to finish completing the construction, but on paper all of the activity has been legal. It’s legal corruption, and it happens all of the time.”
The result is a noticeable tension that hangs in the air. I could hear it in the jokes among locals about being “poor” and “forgotten”. The great debate, then, largely revolves around Puerto Rico’s political status—should it be granted Statehood, independence or remain a commonwealth? Which option will mean greater autonomy and liberation from its longstanding treatment as a ‘defacto colony’? What will ensure the right structure is in place to eliminate localized corruption? These are just a few of the questions citizens seem to be grappling with as ongoing conflicts force them to take a stance.
Beach Bumming
Political turmoil aside, Puerto Rico is known for its beautiful landscapes, including its extensive collection of beaches. Having come from the crisp November temperatures of New York, my plan was to spend a good chunk of my days exploring the several beaches the north coast of San Juan had to offer. And so, over the course of the week I hit Isla Verde, Ocean Park and the more tourist-y Condado Beach—dubbed the Miami beach of Puerto Rico.
It is on these sandy shores that I met folks of all backgrounds. There was a tech patent-approving expat who had been hammock-hopping around the world for the past 10 years. Another, an Oregon-born lawyer who spent the previous year in Saipan helping to rebuild schools destroyed by Typhoon Yutu. Also an Uber driver with a PHD in engineering who was about to launch his own restaurant recommendation business, a French thirty-something who came to Puerto Rico “just because” and a salsa-dancing, Puerto Rican surfer named Ricardo.
During these slower days, I would bake my pale, deprived complexion in the sun, and in those moments of warm bliss understood why so many expats and remote workers were making the move here: You could spend your days basking in the Caribbean climate, enjoy the comfort of still being on U.S. soil, raise a family within a fairly safe environment, while paying rent and other expenses much lower than any other metropolitan area. Of course, there’s also the avoidance of federal income taxes and the resulting displacement and gentrification being brought to Puerto Rico’s local community, but that’s a separate conversation altogether.
Beach days were often wrapped with cheap and delicious meals, my favorite of which included mofongo with shrimp and mango salsa from a food shack, and Arroz Con Gandules, essentially Puerto Rican rice with peas with a side of fried pork belly, from a late-night roadside diner. I’d head home, eyes glazed over from a day in the sun and belly warm and full, ready to sleep it out just to do it again the next day.
The ‘Disneyland’ of Puerto Rico
In addition to beach hopping, I decided early on it would be essential that I visited El Yunque rainforest, the only tropical rainforest in the U.S. It was located on the northeast side of the island about a two-hour drive from where I stayed, and being without a car, I decided to book an organized tour that would provide van transportation to and from the hiking trail.
El Yunque covers almost 30,000 acres, and its lack of dangerous predators makes it a safe place for visitors to go on unsupervised hikes of their own. I distinctly remember our van pulling up to the entrance of the rainforest and seeing a family camped out with a barbecue grill and some plastic stools as the kids played in a nearby river. As my tour guide Andrea put it, “It’s like Disneyland for us Puerto Ricans.”
Upon completing a 30-minute trek through the forest, which included climbing up a near-vertical slab of mud, crossing through rocky, shallow river beds and making the occasional stop to learn about the medicinal flora and fauna, our sore, muddy bodies were rewarded with a series of waterfall slides, rope swings and jump off points into crystal blue springs. A few other tour groups were also present, so our water activities quickly escalated into a spectator event as the men egged each other on to do backflips and jump from increasingly higher cliff points, the highest of which was around 50-feet. I, knowing my limits, called it a day at the 30-foot jump and happily treaded water in the fresh spring pool as I waited for the others to wrap up their stunts.
On Enjoying Your Own Company
I knew the ultimate value I’d derive from this vacation would be to see how I fared on my first official solo trip. And while I’d always considered myself content in my own company, I admittedly felt an unfamiliar level of solitude along with a self-induced pressure to optimize every hour of the day. I suppose I was stuck in a New York mindset in a place that operated at half its pace.
Challenges aside, riding solo also meant I was the captain of my own ship, with no one else’s needs to consider when making plans. Banter and group politics over what to do or where to go were replaced with how I felt on a specific day and acting on whim. I also found that being a unit of one, it was easier to meet locals and fellow travelers who were eager to help me get to my next destination or let me tag along in their plans, again opening up opportunities for my itinerary to change by the hour. With all of this comes a layer of spontaneity and excitement that makes the solo travel experience entirely worthwhile, as I ultimately concluded.
Personal revelations aside, I left Puerto Rico of two minds. On the one hand, I was grateful for the sunny, slow days, which perhaps your typical PR expat or tourist (like myself) could enjoy. But I also left feeling uncertain about the future of the ‘commonwealth’. Stepping out of those picturesque moments, it was pretty easy to catch the tension and resentment that the locals felt towards the government and the way the community’s most pressing issues had been handled. It was as though everyone was holding their breath and waiting for the next catastrophe, whether it be economic, political or a natural disaster, that would bring the territory into an even deeper crisis.
Original film photography below.
