Puerto Rico is a square-shaped rock in the middle of the Caribbean. The Spaniards invaded and took the place over back in the 1500s, then they built a big ass castle on the top corner of the square and started micromanaging all the tradespeople who sailed by.
The English got fed up with the Spaniards’ monopolizing and decided to invade their castle and take it over. That didn’t go down so well and they all died in a field in front of the castle. A few decades later the Dutch tried the same thing and they all died in the same field. Today, people from all nations invade the field to take selfies in front of the castle. It’s quite nice, but you need to watch out for dog shit on the finely cut grass.
I don’t know why I’d never been to Puerto Rico before. It’s the easiest vacation you could ever take. I didn’t even know it was part of the United States (I’m Canadian), but it is in a roundabout way, so you don’t even need a passport when flying from New York. A three-hour domestic flight that costs less than flying to Denver transports you onto a tropical Caribbean island covered with KFC’s and Home Depots. So yeah, it’s an awesome place.
San Juan is cool. Every day, dozens of the biggest cruise ships in the world come in and out of the port, spilling thousands of tourists from Missouri and Germany into the cobblestone streets for three hour shifts at a time, where they dress in khakis and tilly hats for their on-land outings and buy a bunch of Chinese-made souvenirs. This is the best time to wander the streets and go to restaurants because the people-watching is insanely amazing. We sat beside a couple in an Italian joint and it was blatantly obvious they hated each other. He was mid-forties and reeked of wealth and douchery, and she was twenty-one (max), with platinum blonde hair, fake tits, and orange skin. It was apparent that the cruise wasn’t going harmoniously because they didn’t speak or look at each other, and both downed five drinks before their food arrived. And then when they finished (he paid), they went back to their cruise ship to be stuck together for another week. Hahahahaha.
The people in San Juan are great, but so are the people on the rest of the island. We stayed in a guesthouse and the host woman told us of an incredible waterfall hidden in a rainforest near where she grew up. It was only an hour’s drive and she wrote very detailed directions on a bar napkin for us to get to this secret place. “Bring hiking boots for the half-mile trek in and swim in the nude for the real experience”, she said as we left. An hour later after zero wrong turns, we arrived to a half dozen tour buses and a paved sidewalk down to the most blown out piece of shit waterfall I’ve ever been to. I still went swimming and the water was nice, but I kept my shorts on because there were children and elderly Japanese people around.
Most of our time was spent on the north and west coasts of the island, where the surf and beach towns are. First we stayed in Rincon, which is a decent place, but pretty touristy with lots of people like me that I try to avoid. But, we were fresh out of an East Coast winter, so it was fantastic to be sitting poolside at a resort, sipping rum punch and enjoying an endless supply of clean towels. There are no KFC’s or any franchises in Rincon, so it maintains the small town beach vibe. There are waves and spots all over the area and the water is always the perfect temperature. I locked the keys inside our rental car when I went surfing one morning, but a nice teenager with a Raiders jersey and tattoos on his face was hanging out in the dirt parking lot and offered to help. He broke into the car for me with a machete blade and scored the keys. Again, very nice people.
On the north side of the island we stayed in Jobos Beach and Isabela, which were my favorite spots. There’s nothing really there, aside from a few restaurants you have to drive to, a casino, and a golf course. And there’s tons surf all over the place. We linked up with Dylan Graves, who lives there, and Nate Tyler, who was visiting. Dylan is a lifelong local and the king of that place. Rolling with him means instant access to the royal treatment from the whole community. He’s a real good dude and a perfect representation of the Caribbean surf scene. Island vibes, man! Plus, Dylan loves that casino and knows how to properly light it up on the rum drinks.
I think my favorite thing about Puerto Rico is how scenic it is, and I don’t care how lame that makes me sound. There are decrepit abandoned buildings all over the place and all these massive cemeteries mixed into the pastel colors of the little towns. There are also lots of crappy lowered trucks from the ‘90s with energy drink decals all over them and lots of dive bars set up on the sides of the roads. I respect and appreciate the cultural aspect of those who drink rum all the time and do nothing. There’s something noble in that. Now that I know how easy it is to get to Puerto Rico—cheaper and faster than going to Denver—I will be back again soon because there’s a lot more to see. I’d highly recommend visiting the wonderful square island, but don’t go there on a cruise ship and don’t bother with the waterfalls.