Story and photos by James Morley

I didn’t really know what to expect from a trip to Puerto Rico. It was the third time over the past handful of years that Glencoe and I had discussed a trip to the island, and, even though the first two attempts were derailed by exceptional circumstances, the Latchkey Skateboards team had finally settled on San Juan as its destination to escape the unrelenting winter. 

Glencoe Hogle – Backside Kickflip 
These secluded banks look amazing in photos and footage, but they aren’t the easiest place to skate. Glencoe hurt his leg while trying this Backside flip, but he managed to roll away from it while we were getting kicked out. Despite being injured, Glencoe still managed to get clips as well as guide us for the rest of the trip. One morning he drank a bunch of coffee and was totally bouncing off the walls by the time we got into the car. Our drive into Old San Juan was full of abrupt starts and stops as he pointed out spots and landmarks on either side of the road, getting more and more energized the whole time. It was one of the most entertaining things I’ve seen in a long time, even if the drive was a bit bumpy. 

I was already itching to get away to warmer temperatures, so I was more than ready to tag along when the opportunity presented itself. I had done very little research about our destination, but Glencoe only had positive things to say about the place when we tried to plan the trip before, so I trusted his judgment and looked forward to seeing what we were getting ourselves into.

Once we arrived in San Juan and settled into our Airbnb, we quickly adopted a new routine. We would begin each of the next six days at the grocery store by eating cheap acai bowls and stocking up on water before traveling to one of the nearby areas and explore the plethora of bust-free plazas and spots littered all over the island. Then, we would head back to the apartment each evening to hang out and drink on our private rooftop patio, eventually wandering to the local plaza for the rest of the night. Though this cycle made our week in the hot, tropical temperatures somewhat physically demanding, it also gave our trip the perfect harmony of productivity and relaxation that we were all hoping it would.

Neil Blackwood – Backside Flip 
After playing Frogger to make it across the highway, we ended up at this spot. The sun was shining at an inconvenient angle and there was a strong headwind—not exactly the optimal conditions for skating a long flat-gap after spending all day in the sun. Neil took a few roll-ups to gauge his speed before rolling away from the first one he popped. Neil’s skill on a skateboard is matched by his incredible ability to add a healthy dose of puns to any situation, as made evident by his quick renaming of our rental car (which quickly became the “Latch-Kia”) and identification of accidental wordplay in our otherwise ordinary dialogue throughout each day. We also discovered that Neil can spin a plastic lunch tray on one finger with an uncanny level of balance and ease. Ask him to see it next time you’re at a fast food restaurant.

By the end of the week, Puerto Rico proved to be the best skateboarding destination I’d ever seen, and it made for the best skate trip I’d ever been on. We were all sad to be flying back to the Canadian winter, but there’s nothing like a healthy dose of misery to make us look forward to our inevitable return trip in 2020!

Will Filion – Backside 180 Nosegrind Revert 
On the way to this plaza each night we would pass a gas station that turned into a hub for drinking and partying after sunset. We would see a crowd of people hanging out there every evening, and a pile of leftover garbage and bottles every morning. One particular night, Glencoe and Will were passing by and caught the production of a local rapper’s music video in the gas station’s parking lot. Between the barbecue’s flames running beside the gas pumps and an old man sandwiched by two bikini-clad dancers, that evening was so bizarre that I doubt anyone would ever believe that it happened. Luckily, a few well-captured cell phone videos documented the madness and entertained us for the rest of the trip.
None of that really relates to this photo, though. We skated the plaza every night and became quite familiar with it by the end of the trip. Will started trying this Backside 180 Fakie Nosegrind Revert while we were there in daylight, and, coincidentally, I had been hoping to try and shoot one from this angle for quite some time. He got the trick, and everything worked out.

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