Anticipation hung in the air like a bad cologne as we shuffled through the security line, bleary-eyed and barely awake. Seriously, we were running on fumes—less sleep than a college student during finals week. The night before, we had strutted into Starbucks, caffeine-fueled and boasting about our epic adventure. There we were: my dad, and my two friends, Adam and Frank, practically vibrating with excitement like kids after a sugar rush.
To prep for our adventure, we’d stocked up on energy drinks for the drive from Oklahoma to Dallas, convinced we’d need them to survive the flight. So, naturally, while standing in line, we cracked open a couple of those bad boys—Redline energy drinks, no less. Nothing says "smart travel decision" like guzzling caffeine on an empty stomach. By the time we boarded the plane, we were practically doing interpretive dances in our seats, full of energy with no outlet.
As we taxied down the runway, I was practically bouncing in my seat. The engines roared, and before I knew it, we were airborne. Our first layover was in Florida, where we refueled with sandwiches that finally gave my stomach some resolve. After more movie-watching on Dad's laptop and some enthusiastic journaling, I glanced out the window, and boom—nothing but water.
I decided to pull my best Indiana Jones impression, pulling down my hat to catch some Z’s. What followed was a descent so beautiful I could’ve cried—boats bobbed in the sparkling water, and then, like a scene out of a postcard, Puerto Rico came into view. It was love at first sight.As we approached I looked down and saw boats on the water. The island was coming into view. I felt my excitement rise and a smile crept on my face. There it was: Puerto Rico…
Once we landed, we grabbed our bags like they were golden treasure and hopped into a cab, ready to embrace the Caribbean life. The moment we checked into our hotel, I was out the door faster than a kid on Christmas morning. “Where are you going?” Dad called after me. “For a drink!” I shouted, already imagining the rum flowing like it was a tropical waterfall.
As I approached the bar, the dulcet tones of Bob Marley greeted me, like a musical hug. I ordered “Ron de Barrilito” mixed with Coke—pure island bliss. One by one, my companions joined, and we struck up conversations with a couple of girls from Texas. After a few rounds of shots—who knew they were so persistent?—we made plans to meet up later, blissfully unaware that this was a classic recipe for chaos.
Drunkenly, we made our way to our first authentic Puerto Rican meal at “Bebos.” Thanks to my Spanish skills, which was a skill I had actually underestimated, I was complimented by our waitress—turns out “Gracias” and “Una más cerveza, por favor” aren't the only phrases you really need to know. That night, we got an up-close and personal view of the beach, which was basically Mother Nature’s version of a tropical runway show.
We decided to hit the grocery store the next day, stocking up on Ron de Barrilito and Medalla (meh-daya) beer (which sounds like a fancy medal, but trust me, it’s just beer). We were a bunch of happy, drunken pirates on the beach that night. Dad took a nap while I led the charge to explore San Juan, only to discover that “La Ventana del Mar” was about as elusive as my willpower at a buffet. We never did find the place, but we pissed away money all along the way. We ran into a couple of locals named Pedro and Camilla at a charming spot aptly dubbed "Buddha Tai."
Day two featured a cheap breakfast with coffee strong enough to wake the dead, and we jumped on a bus to explore “Old San Juan.” I marveled at El Morro, the historic fort, imagining pirates scaling its walls—this was way cooler than my childhood fantasies. That night, after dressing up, we hit a spot called “La Placita de (Something),” where I made friends with everyone from around the globe. Little did I know, the bartenders there might as well have been ninjas—one minute you’re sipping on rum, the next you’re doing the salsa like a drunk penguin. They really know how to pour their rum in P.R. Everyone eventually went to bed, except Frank and I. We met some more people and mingled, then we retired late.
By day three, we were suffering from serious fatigue. After downing a pizza larger than my face, we ambled around checking out local shops and more importantly, tattoo parlors. Dad decided to catch some Z’s while we hit the beach—where, I kid you not, it was like being surrounded by goddesses. This truly was La Isla Del Encanto!
Later, we showered and headed out again for more adventures after guzzling down another piña colada from the hotel bar. We asked the bartender where a good place to go was. We found out when we got there that it was a formal place. So we took another cab ride to Old San Juan again. We discovered a bar where beer was two dollars a can—tax-free! Cue the happy dance! We then found Club Milk, which had a dance floor that looked like a scene from a telenovela. Even though my dancing resembled more of a hippo trying to swim compared to the dancing in this club, we left early, my heart a bit heavy that I hadn’t mastered moves like that.
On day four, our wallets were running low, but my ambition was high! Lunch at “Fuddruckers”—the burgers were delicious but took so long, I almost forgot how to chew. Our server was this guy from Florida who claimed he went there on vacation and just never left. Turns out, he’s a modern-day pirate—flipping burgers instead of sailing the seas! Afterwards, we reconnected with those girls from Texas, who had decided to bless us with their rental car. In the back seat, we were like sardines packed together, which, let me tell you, is not the most dignified way to roll around San Juan.
During the ride, I witnessed a brown boy perform an impromptu dance that left us in stitches. After a gas station pit stop with a questionable character begging for change, we ended the night with overpriced pizza. I also snagged a leather bracelet from a street vendor, which I promptly decided would make a great tattoo. Because nothing says “permanent decision” like a drunk shopping spree.
That night at “The Oyster Bar,” we and our new lady friends learned how to salsa. Or, at least, we tried to learn while likely embarrassing ourselves.
After our night out, we decided to hit the beach with the girls on their last night, and let me tell you, it became one of the most unforgettable nights of our trip. I found myself developing a bit of a crush on Carly. We swung by a store to stock up on rum and beer, chatting with some locals along the way.
When we returned to the beach, Dad and Frank had a rather “spiritual” experience involving a substance of some sort—very generous of the girls to share that! We even crafted some epic sand penises and struck ridiculous poses on them. Pure chaos and laughter ensued.
Later that night, we ended up back at the girls’ hotel, cramming ourselves into a massive hot tub and getting way too drunk. Adam decided to mark his territory by peeing off the side. When Carly headed off to bed, I noticed her room key sitting on a chair and thought that I should bring it to her. So, I grabbed it and made my way to her room—okay, more like stumbled my way there.
I managed to unlock the door, but then I heard the shower running and realized she’d made it in just fine. I put the key on the bed, but then it hit me that Dee might need it to get in. Just as I turned around to head back, the door creaked open behind me. To my utter delight, I found a dripping-wet Carly in a towel. Before she could say a word, I spilled my whole key situation.
It wasn’t until the next day that I realized the golden opportunity I’d just missed. Not that I would have made a stellar impression anyway—let’s be real, I was at a level of inebriation that would have made me a total letdown!
The next day, we woke up late, as expected after a night of wild dancing. We treated ourselves to a delicious Cuban meal that knocked our socks off—definitely a highlight of the trip. Later, we set out to find a seafood dinner, but it was so overpriced and underwhelming, we felt like we were on a cruel reality show.
Finally, with a renewed sense of adventure, we rented a car and discovered the rainforest of El Yunque (El Joonkay). My heart warmed as I bought my son a stuffed parrot—who could resist that? (I called my mom and talked to him that day.) We trekked around, and I even spotted a Chupacabra sign. We enjoyed fresh ice cold coconuts like the tourists we were. We hiked in the rainforest and took a refreshing swim in a waterfall fed pool of cold water at the end of our hike.
Once we got back from our rainforest adventure, I ended up getting a skull and crossbones tattoo on my leg—a design I had drawn myself. It was inspired by a little trinket I’d picked up earlier in the trip.
After breakfast the next day, we hopped on the ferry to the island of Culebra. And let me tell you, that boat was colder than a walk-in freezer! They were playing "10,000 B.C." on the screen, so at least we had some entertainment. Two chilly hours later, we arrived at La Isla de Culebra. We kicked things off with some more “Pinchos de Pollo” (chicken on a stick) before grabbing our snorkel gear and trekking over for another long walk. It was worth it, though—at one point, Dad almost bumped into a jellyfish underwater. We joked about how we'd have to resort to some “emergency peeing” on his head if things went south.
Afterward, we ventured to the other side of the island to La Playa Flamenco, where we found the whitest sand and clearest water we'd ever laid eyes on! I sipped on some Don Q rum, our go-to island choice, and soaked in the moment. We headed back sunburned to a crisp and treated ourselves with a blend of aloe and apple cider vinegar—needless to say, we smelled fantastic.
Finally, our last day in the Caribbean rolled around. We spent a bit more time wandering around Old San Juan before it was time to head out. I was missing my little boy so much that I was ready to be home. But ever since I left the Island of Enchantment, I’ve been longing for those beaches, the memories, and, of course, the beans and rice.
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