16 Friends, 1 Island : Puerto Rico Group Trip
30 minute experience
“I did zero prep for learning how to surf – aside from watching cool surfing videos, of course! As the wave comes closer, I feel the anticipation, the rush of trying something new. Laying on my stomach, I start paddling as fast as I can…”
My friends and I have gone on adventures for close to a decade, no matter rain, sunshine, or snow, from music festivals, to beach houses, to camping in the woods. But one thing we've never done is fly all 16 of us to a Caribbean island – it’ll be our greatest adventure yet!
December of 2025, we left cold and snowy Pittsburgh for hot and humid Puerto Rico. It was a whirlwind of activity booking everything, but after much discussion, we finally pulled together for the experience of a lifetime!
At 3am on a cold December morning, we piled six people into a five-seater truck, our backpacks and luggage just barely fitting in the back. The Pittsburgh airport has just been renovated, and we’re about to give it a test run…
Table of Contents:
A New Airport
We park in the extended economy parking lot (now the shuttle lot). It’s dark, cold, and windy, but we’re wide awake, ready to start our first day of vacation.
We’re supposed to find a shuttle stop, but looking around, we don’t see anything. Not knowing where to go, we follow a small crowd walking down the old terminal ramp. But when we reach locked doors at the end of the long hallway, we realize it’s the blind leading the blind.
We call airport employees, talk to strangers, and waste an hour walking around aimlessly until we finally reach the shuttle stop – it’s 100 yards away from our car! A simple sign reading “Airport shuttles this way” would go a long way for the $1.7 billion airport upgrade! Alas, we make it onto the shuttle, our fellow wanderers on board with us.
It’s 5 O’Clock Somewhere
I make it through TSA, but just barely – my unmarked 15-ounce tub of coconut oil gets flagged down as “suspicious”. I stopped wearing sunscreen several years ago, so instead I use coconut oil and homemade moisturizer to heal my skin after long days in the sun. Luckily the coconut oil is rock-hard from the cold temperature outside, so it passes further inspection.
We meet up with friends in the food court, but only temporarily, since we fly out on different planes. The excitement of a new adventure bubbles up inside us, so when the airport bar opens up at 5am, we cheers mimosas and espresso martinis to “Puerto Rico!”
Vrbo in San Juan, Puerto Rico
Two planes and eight hours later, the warm, wet air kisses our cold, dry skin. We call for an Uber outside the San Juan airport, ready to meet our new home for the week. The rides here are surprisingly cheap – only $15 for a 15 minute ride.
There’s three floors to the house, the third floor being a rooftop patio (and our favorite hangout spot). Other features include a small private pool, dedicated A/C in every room, and a short five minute walk to a beach!
Outside, lizards big and small dart across our feet, and flocks of chickens squack and cross the road at their own leisure. Once it gets dark, we hear the locally famous coqui tree frogs calling out for mates.
Around the corner, just 60 seconds from the house, is a lifesaver – a grocery store! We pick up food and supplies at their own leisure, making things easy and convenient for everyone. I loved going for juicy papayas and fresh bananas, and coconut water became my drink of choice.
Our first night is laid-back, filled with board games and hanging out. It’s been a while since the last big group trip, but for the next week, we’re excited to make all new memories together here in Puerto Rico.
Sunrise and Coffee
We start our first morning out in Puerto Rico early– at 6:15am we’re headed to watch the sunrise. I’m fairly awake, considering the rooster that was cock-a-doodling outside our bedroom window since 3am!
Fifteen minutes later, down a curious concrete alleyway, we find a tucked-away beach all to ourselves. We wade into the warm ocean water as the sun rises and lights up the sky – it’s the perfect start to our vacation.
After we ground ourselves in the sand and sea for a bit, we walk over to a local coffee shop, 787 Coffee. There’s a bunch of people (my friends) in front of me, so I have plenty of time to rehearse my coffee order in Spanish: “Buenos días, un café con leche por favor! :)”
We sip coffees under the shade of the front patio, joined by a rogue cat and a chicken, both hanging out just beyond our reach.
This afternoon holds the first scheduled event for the trip: a Bacardi Mixology class. But only a few of us go, the rest heading to Old San Juan. I talk to the friendly driver during the 20 minute ride to Casa Bacardi, and he gives us dinner recommendations for Old San Juan for later.
Bacardi Mixology Class
We’re dropped off at what feels like a college campus; a towering pavilion houses the check-in desk and a bar, and a huge lawn spreads out behind it. To the left are holding tanks for millions of gallons of sugar cane juice alongside old stone buildings and modern offices.
On the lawn there’s a bat sculpture and a huge banyan tree. To the right are wind mills, and beyond that, the Bahía de San Juan (San Juan Bay).
We walk around admiring the property for a few minutes, but soon we’re called for the start of the tour. A cheerful woman named Violeta takes us on a short and simple trolley ride, describing the manufacturing process of their rum, the layout of the campus, and Bacardi’s history…
She tells us Bacardí’s iconic bat logo stems from its founding days in Santiago de Cuba in the 1800s. When the Bacardí family bought their first distillery, fruit bats were found living in the rafters — in Spanish and Caribbean cultures, bats represent good fortune, health, and family unity.
We learn that the yeast that creates Bacardí’s signature taste is the same yeast since 1862 – and only five people in the world have access to it!
The short trolley tour ends, so we head to the mixology room where Violeta shows us how to make mojitos.
As we measure, mix, and pour our drinks, she says mojitos actually started as a warm drink used to help with digestion. Living in the hot tropics though, it was only a matter of time until they added ice and alcohol!
Feeling like sophisticates now, we drink our Mojitos and Hotel Nacionals and take pictures of the recipes for later use.
Our tour finished, we contact the others and arrange for dinner in Old San Juan. There’s a ferry that takes us across the bay for only $2, but even though we’re “on time”, the boat fills up to capacity, so we wait until it comes back.
Aboard the ferry thirty minutes later, we witness the seacraft in the bustling harbor, from small private yachts to the larger-than-life cruise ships.
Stepping off the ferry, we walk uphill through Old San Juan to meet our friends at El Jabirito. I can’t help but get distracted from the pastel-colored buildings, the narrow, blue-colored cobblestone roads, and the balconies hanging into the streets from overhead.
We walk inside to find everyone seated in the upstairs loft at one long table. I don't know how our group of 16 got seated all together so easily, but I wasn’t about to start asking questions!
With dinner finished, we head back home and log a successful first day in Puerto Rico.
My First Time Surfing
It’s only the second day of our trip, but all year Ivan and I have been talking about surfing – I’ve never been, and Ivan only a couple times. Yesterday at Tres Palmas, a local surf shop, we were told the best place for two dudes without surfboards, a car, or experience, would be Pine Grove Beach.
It’s a beautifully sunny morning full of potential. Just a 10 minute ride away from the beach, we arrive and see surfers just 30 yards offshore. Conditions are perfect, and the only thing beating the conditions is the price – two hours of surfing for $25 through Pine Grove Surf Club!
Ivan and I walk up to the tent, and a man named Pedro jogs up to us fresh out of the waves. He confirms our online reservation, grabs us a pair of beginner surfboards, then cuts us loose. We march the 8-foot foam boards into the warm salty water, and once we’re chest-high, we hop on and excitedly wait for a big wave.
I took a gamble and did zero preparation for learning how to surf – aside from watching cool surfing videos online, of course! Instead, I’m relying (heavily) on my intuition and past snowboarding experience...
Surf’s Up!
Spying a wave in the distance, I tap into the ocean’s energy coursing through me. As it gets closer, I feel the anticipation, the rush of trying something new. Laying on my stomach flat on the board, I start paddling as fast as I can…
I’m picking up speed, but I still don’t really know what I’m doing. I hear the wave curling, and I see white water rushing beside me. Finally I push myself up and plant my feet on the board. It’s not too hard to balance myself, but it doesn’t last very long…
My center of balance is too far forward, and the tip of the board dips an inch or two underwater. Even as a beginner, I instinctively know that’s a recipe for disaster! Instantly the wave throws me forward and crashes perfectly on top of me.
Salt water rushes into my nose and mouth, and I tumble around feeling like a load of laundry in the washing machine. For a few seconds, I lose myself in space and time. I throw my arms over my head, trying not to get smacked by the surfboard still connected to my ankle…
Amidst the chaos, I’ve learned from years of beach-going the best thing to do is relax. Mentally I collect my bearings but stay cautious – the ocean floor is only a few feet away, and I don’t want to step on any rocks that may lie hidden beneath me.
Finally emerging from the surface, I feel like I’ve just gone through an initiation. I yank my surfboard back, dodge an incoming wave, and look back to see Ivan with his hands in the air, cheering me on. Dopamine floods my brain, and I scramble back onto my surfboard, excited to do it all over again!
After what feels like two hours, I head ashore for a short break from the saltwater. But time is warped, because when I check the time, it’s hardly been an hour! Pedro, who’s been surfing with us the whole time, loves our enthusiasm and says we’re welcome to use the boards all day!
Pine Grove Beach: Sand, Surf, and Volleyball
Alive with new energy, we regroup with everyone back at the house around noon — today’s our dedicated beach day, and we’re eager to drag everyone back so we can go surfing again. With lunch eaten, no objections, and everyone's gear packed up, we head back to Pine Grove Beach.
Almost instantly Ivan and I grab the surfboards again, this time with Mayson. There’s a recent influx of seaweed in the water, making the water feel itchy, but that doesn’t stop us. We paddle out past the seaweed, and soon there’s three dudes on surfboards taking on the waves.
The waves were good a few hours ago, but now they’re intense – wipeouts are had, seawater is swallowed, and only one of us has a quick puke in the water. Nevertheless, we’re surfing Mother Nature’s tests. But with some waves ridden and my sinuses bombed with seawater, I finally ride a wave in and pass my board off to Luke.
On my break from surfing, I go on a walk with Rachel and Liv as they find seashells and pretty pieces of coral. The unique and varied bits of sea life gives us a sneak peak – not only of the coral reef a thousand feet offshore – but what we can expect when we go snorkeling in a few days!
There’s seaweed-free water a short walk from our outpost, so a group of us go body-surfing and dive through the curling waves. Some of us get smacked by quiet killer waves, but all of us laugh and carry on anyways. But as the waves get bigger still, we soon fall into temptation – Luke, Ivan and I run over and grab the surfboards for one last session!
We’ve (barely) learned how surfing works – but we’re tired from the day, and the wipeouts still hit hard.
Finally tuckered out from the relentless ocean and the hot sun, we return the surfboards back to Pedro. I appreciate him letting us use the surfboards all day, and he’s impressed at our morning, afternoon, and evening surfing sessions. He says he loves our group’s vibe, and just based on our short conversations, I realize he’s a real one.
The Perfect Beach Day
You’d think I’m too tired by now to do anything else – you’d be wrong!
Some friends are playing sand volleyball down the beach, so like a toddler with unlimited energy, I run over and join the game. Still wet from the water, I dive for the ball and I’m instantly covered in sand.
But soon the sky glows a warm orange splattered with streaks of red and yellow – a sign that our amazing day at the beach is about to end. I want to take a picture, but my phone is across the beach – besides, I’m having too much fun in the moment.
Trying to get a ride back home, however, is a different story; Uber drivers would accept the ride, show up, then speed away and cancel the ride once they saw our swimsuits, chairs, coolers and towels. A half hour (and three drivers) later, a gentleman finally takes us back, so I give him our thanks and a nice tip.
(Travel Tip: If you need a ride from the beach, do your best to make it look like you’re not coming from the beach!)
It’s a quiet night at the house – tomorrow morning, we’re going hiking!
El Yunque National Rainforest
Puerto Rico is full of amazing experiences – but if you only do one thing, I recommend hiking El Yunque National Forest.
There were very few options for a 16-person group tour, but our group went on separate tours anyway; nine went and did a walking tour, so I took seven people on the “Off the Beaten Path” Trail.
The tricky part, however, is no rideshares are allowed inside the Park. That means unless you’re renting a car, you must schedule a tour that includes pick-up from wherever you’re staying.
Dog watching traffic from a balcony as we wait for our ride
At 7:50am we’re standing on the street corner ready to get picked up. I forgot to reply to the confirmation text yesterday to confirm our booking, so I’m a little bit nervous! It’s already a few minutes past eight, so I have to remind myself we’re on “island time.” A few minutes later, a black 16-seat sprinter van finally pulls up.
(Travel Tip: If you’re traveling outside the mainland USA, relax your expectations for timeliness. Most people aren’t stressing out about a few minutes here or there, and you shouldn’t either!)
Jason, a Puerto Rican native and our guide for the day, jumps out with a warm smile on his face. His smooth, grounded, “Spanglish” accent instantly tells me we're in good hands. We pick up a few other people joining us for the tour, and soon we’re on the highway bound for El Yunque National Forest.
It’s about an hour drive from San Juan to the trailhead, but on the way we make a pit stop at Walgreen's. Here Jason describes the hike conditions (wet and slippery) and what we’ll be doing (a water slide, rope swing, cliff jumping and more) and lets us pick up any last-minute supplies we may need.
The “Off the Beaten Path” Trail doesn’t pass through the welcome center – instead, we pull up to a small gravel parking lot, a family-owned property serving as a back-door entrance to the forest’s hidden features. The mountains looming overhead are covered in dense fog, and the whole forest exudes a saturated environment teeming with life.
We hop out of the van and Jason passes out lifejackets. Looking around, I’m astonished by clusters of huge six-inch-diameter bamboo stretching high into the sky. It’s warm out, so following Jason’s lead, we go shirtless – a confirmation that Jason knows how to ground himself.
The hike climbs 700 feet in elevation – not too hard for active 28 year-olds. Close-toed sneakers are required, so I brought a pair of running shoes I fully expected to wear in the water. It hasn’t stopped raining since we left Walgreens, but we’re told this is normal…
“Off the Beaten Path” Trail
As we start up the trail, Jason describes the history of El Yunque, periodically stopping to show us the local fauna and flora of this unique jungle. There’s over a thousand different species here – many are endangered and only found in this rainforest, and many are transplants from other parts of the world. Jason jokes “hundreds of species flock here during the wintertime – just like you!”
Puerto Rico doesn’t have venomous snakes – just huge boa constrictors that grow 16 feet long! Jason says it’s OK though – just like other Puerto Ricans, they’ll only want to hug you!
El Yunque is the only tropical rainforest in the US forest system, and Jason says it can rain here up to 9 inches per day! I almost didn’t believe him, but a google search later tells me it’s true!
In 2015, Hurricane Maria wrecked Puerto Rico; large trees fell, vast flooding reshaped the landscape, and wildlife was majorly disrupted. It’s recovered since, but signs of the devastation can still be found.
Jason shows us the popular, wide-spread “paper tree” from Mexico, the yagrumo tree. It grows well here because they’re the first trees to regrow in open, destructed areas (such as after a hurricane). The locals have learned to use these trees to predict storms – when strong winds expose the white undersides of the leaves, you know a storm is coming!
Jason spies a ginger plant with some flower blossoms and excitedly plucks one. Ginger roots are used for medicinal purposes worldwide, but he rips the flower into pieces and passes it around for us to eat. I didn’t know some flowers were edible, and this one offered just a subtle hint of sweetness.
One of my favorite plants – that I almost forgot lived here – is the Touch-Me-Not plant, also known as Shameplant. Jason finds one and bends down to the small shrub growing on the forest floor. He touches a leaf, and almost instantly the plant folds into itself! This is harmless to the plant, so we all take turns touching the plant and watching this amazing natural phenomenon.
The soil here is rich with nutrients, and we see just how much – almost every group of people we pass has mud smeared on their faces! The tour guides of the other groups were all very friendly and upbeat too, and every time we passed them, they yelled out to us “We love Jason, he’s the best!”
Water Slides, Rope Swings, & Cliff Jumping
After a short uphill walk, and some mud slathered on my face, we descend into a beautiful river valley. At the bottom, rushing clear waters and lush greenery expose the vibrancy of the forest, leaving everyone in awe.
To the left, people jump into the river beside a small waterfall. Straight ahead is a rope swing where tour guides show off their backflips. To the right the stream continues downhill, where some people ground themselves in the El Yunque mud.
But the “off the beaten path” part is just starting! Onward and upward we march through the rainforest. It’s not for the faint-of-heart — we scramble over soaked boulders and gnarled tree roots, careful not to slip – but Jason helps us every step of the way.
Finally we reach the first feature – the natural water slide! Carved into the rock, it’s 20 feet long with a small bend at the end, right before it dumps you into a small pool. I considered going down head-first, but after watching others go down, I’m glad I didn’t – it was a good water slide, just not the smoothest!
Although we all know how to swim, the lifejackets are very convenient as they shoot us back up to the surface. From the cool pool we scramble to the top of a huge boulder, and Jason takes videos of us as we jump back in from 15 feet up.
Jason the Redeemer
Just around the corner is a “cave” that’s been carved through a huge boulder. The channel is half underwater though, so it takes some coordination to swim upstream and make it all the way through the opening. As we line up to swim (squeeze) through the narrow passageway, Jason says “Get ready for your Puerto Rican re-birth!”
Following our makeshift baptism, we hike back down to the bustling river valley, and those who dare scramble up a 25 foot rock. I’ve jumped into water from high up more times than I can count, but I still can’t help but get nervous every single time!
Finally we reach the last feature of the excursion — the rope swing. Jason tries showing us how to do a back flip, but the truth is he makes it look easy…
Swinging out over the water, leaning back as hard as I can – I land flat on my back! Luckily the lifevest takes the brunt of the fall, and I wade out unscathed. Jason redeems our group with an effortless backflip, surprising no one, before we all climb out of the river valley to head back to the van.
Walking down the trail, we caress the Touch-Me-Not plants one last time, then stumble upon a huge snail! Hanging out on the end of a stick, jutting out in the middle of the trail, it’s the biggest snail I’ve ever seen!
Piling into the van, I realize how exhausted I am, and once we start moving, I doze off...
I wake up as we pull into Asador Boricua, an outdoor restaurant reminding me of my time in Costa Rica. The stop for food is part of the trip (but not included), and I have full faith in Jason’s restaurant choice. I order coconut rice and mofongo (a Puerto Rican staple of mashed plantains with butter) and after my first bite, I realize this is the best food I'll have all trip!
Fancy Night in Old San Juan
It’s been an adventure-filled day so far, and we’re due for some down time at the house. But once we’re recouped, we dress up and make our way to El Asador in Old San Juan. When we walk in, a miracle happens – they seat all 16 of us together!
We sip fancy drinks, order expensive meals, and enjoy the banter of our big group all seated together once again. After dinner, the call for dessert pulls us down the street for a short walk to Anita Gelato. Here I enjoy a dark chocolate gelato cup in the warmly lit, Christmas-themed streets of Old San Juan.
We head back to the house to wind down, eager to get a good night’s sleep before tomorrow’s big activity…
Catamaran Party Boat
Even though it’s 9am, there’s just something about being on a boat in the tropics that screams “party time!” After an hour ride to Fajardo, we climb aboard the Barefoot catamaran, a fully-booked 50-person capacity boat by Castillo Tours.
The crew gives us a quick rundown of the rules of the boat, and we yell out “hoorah” before we pull away from the dock. But our “hoorah” was weak, and the crew offered to leave all the alcohol behind! They give us one more chance to redeem ourselves, and this time we yell “HOORAH!” as loud as we can.
With the tone set and drinks in our hands, we sail out to sea…
Some friends and I sit in the front of the boat, chit-chatting and admiring the scenery for the 45 minute ride to Icacos Island. Looking back, we see the misty mountains of El Yunque looming over the island. To our left, we spy the El Conquistador Resort incline, a chilling reminder of the Monongahela and Duquesne inclines we left behind back in cold, snowy Pittsburgh!
I’m on my third Captain’s Special by the time we drop anchor in the 80°F, crystal-clear water of Icacos Beach.
We’re eager to wander around the barren island, so we step off the boat into chest-deep water, drinks raised high so seawater can’t get in. Behind us, the crew throws two things into the water – a floating mat for us, and a raft for drinks! The makeshift bar bobs up and down in the waves, so when refills are needed, we hold it down while they pour our drinks.
We only walk 50 yards down the beach – when you’re already in paradise, you don’t need to go far! The sun, the sand, the water, and my best friends, all blended together perfectly in Puerto Rico. I remind myself how special a moment like this is for me and 15 of my favorite people.
Around noon lunch is served; build-your-own sandwiches, snacks, and pasta salad. There’s enough for seconds, but instead a few of us sneak back to the beach, getting swept away in conversation. Soon though we’re called back onto the boat – it’s time to go snorkeling!
Snorkeling
We patrol a few minutes to a nearby coral reef, and the crew gives us instructions for using the fins, snorkels, and goggles. For safety, they string a rope between our boat and another friendly boat, the Spread Eagle. They finally let us loose with just one warning – “don’t touch the big brown mass of coral out in the water – it’s a living creature!”
Lots of people are feeling their drinks by now, so snorkeling doesn’t sound so appealing to some. But my friends and I are here for adventure! We (haphazardly) jump in – some without goggles, some without flippers, and some without snorkels – but all of us together!
With (all) my snorkeling gear on, I gently float on the surface of the water. The ocean floor is 20 feet below us, but you can still see a wide variety of fish, coral, and ocean life through the translucent water.
A few minutes go by, and I find myself floating over some coral just five feet off the surface of the water. I usually only get this up-close-and-personal view through a screen, but here I am physically immersed in this incredible encounter – just arms-length away!
As I soak up this coral environment, a faint whistle sounds off in the distance, creating a ripple in my magical experience. It takes a second, but I realize the whistle is for me – I’m hovering over the brown coral mass they warned about!
I snap out of my hypnotic state and swim back to join the other snorkelers. I try snorkeling in other areas around the boat, but none compared to my experience with the forbidden brown mass…
Back on the catamaran, the crew continues handing out drinks (now adjusting the alcohol according to who’s asking!) The music is blaring, so the crew blows whistles to get everyone’s attention – not for something critical on the boat – but to make sure everyone starts dancing to the next song!
Finally we set sail back for the dock, but that doesn't mean the party is over — shots are poured literally as we’re pulling up to the dock! But eventually the engine stops, and our chaotic, crazy, Caribbean catamaran trip finally comes to a close. Of all the activities on our Puerto Rico trip, the catamaran turned out to be the group’s favorite.
San Juan Clubs
Even though we spent all morning partying on the boat, it’s also the only night for us to go clubbing in San Juan. With (mostly) everyone recouped from the day on the boat, we dress up and call rides to Garabatos.
Stepping out of the car, I can tell we’re in the right spot – flashing lights and giant screens light up the busy street, and music blares from bars on both sides. You don’t even have to be in a bar to dance – or drink!
(Travel Tip: You can walk out of PR bars with drinks in hand!)
Eventually we walk across the street to a crazier place, Aguardiente Bar. The dance area is small, but people are crammed in. In the corner is a raised platform with a pole – Paige hops up and starts spinning around, but soon gets booted off by some other woman’s powerful booty shakes.
I step outside to get some fresh air, and in back-to-back instances, I’m flabbergasted.
First, I see a guy walking around with a monkey – I don’t even know if monkeys live in Puerto Rico!
Then — not even a minute later — I see a man with an albino python! The police drive by – not just to monitor the night life, but to have a legitimately friendly conversation with the snake man!
But by 12:30am, we’ve had enough. It's hard to squeeze as much as you can out of every day while on vacation – you can only know your breaking point once you reach it!
Caffeinated Thoughts
With just two vacation days left, the chance for a slow morning finally reveals itself – upon waking, a smile crosses my face, and I take a deep breath.
Armed with just my phone, credit card, portable keyboard, and my minimalist Earthrunner sandals, I stroll 20 minutes to Kasalta, a bakery recommended by Jason a few days ago. I order coffee (in Spanish, of course) then write a short blip about one of my favorite times in Puerto Rico so far – surfing.
But as I sit and type, I realize that when I’m surrounded by friends or family for an extended time, I can become ungrounded.
The barrier between myself and others slowly dissolves, and the energy of my environment envelopes my being. Instead of remaining centered in myself, I’m vulnerable to rigid postures and old thought loops…
It’s easier said than done, but taking time to center myself again is self-care that should be prioritized.
The only predicament is that the FOMO is real! With such a big group of friends full of diverse personalities, anything crazy can happen at any moment — I don’t want to miss out on spontaneous core memories with my closest friends!
Heading back home, the bright sun, the hot air, and the ambiance of island life throws me into a heady spiral; I’m suspended in euphoric energy with every step, and I romanticize what life here could look like...
Surfing warm water
Writing at coffee shops
Painting from ocean-front balconies
Grounding myself barefoot on the beach
But back at the house, I’m quickly faced with a harsh reality…
(Almost) Bioluminescent Kayaking
Puerto Rico has several places to go bioluminescent kayaking, but Mosquito Bay is supposed to be the best. The only down-side is it’s not on the main island. To get there from San Juan requires:
An hour drive to Ceiba Ferry Terminal
Then a 45 minute ferry ride to Vieques
Then a 15 minute taxi ride to Mosquito Bay
It’s risky business – our scheduled tour starts at 6:30pm, doesn’t end until 8:30pm, and the last ferry back to Puerto Rico leaves at 9:30pm. If we miss the ferry back, we’ll have to buy a hotel room somewhere in Vieques – or cuddle up with the lizards and crabs on a beach!
A Blessing in Disguise
As we’re figuring out the logistics, I realize that leading up to this trip, I was looking at the wrong ferry schedule! Looking at the correct schedule now, between online and in-person tickets, the seating is very limited – less than 15 seats are available. This fact alone is enough to hijack our plans…
Ideally we’d reschedule our booking, but we can’t do that either – tomorrow is our last day, and if we miss the ferry tomorrow night, we’ll also miss our flights back home!
Long story short, no bioluminescent kayaking for us…
What bioluminescent bay kayaking would’ve looked like
Unfortunately this was one of the main things I wanted to do in Puerto Rico – a fully-clear bio bay kayak tour for 16 people in the best spot – but I learned the hard way that with big groups of people, it’s better to be practical than idealistic.
(Travel Tip: If I could go back in time, I’d opt for the second best place, Fajardo, to go bioluminescent kayaking. It’s only an hour drive away, and despite the three-quarters-full moon at the time, we could’ve at least attempted to see the rare glowing bacteria.)
We could still book something last minute in Fajardo, but after losing $57 to our booking, it felt forced. Perhaps it was all a blessing in disguise – that we didn’t get stranded overnight in Vieques!
It’s cloudy outside, but the only thing to do now is head to the beach. We walk a few minutes to the closest one, lay out our towels, and unwind from the tension. I brought my drone, and once the wind dies down, I launch it over the ocean before the sun goes away for the night.
Old San Juan: Shops, Castles, and the Beach
We wanted to check out Old San Juan after the Bacardi tour the first full day, but we were short on time. So the morning of our last day we take advantage of the wide-open plans ahead of us.
(Travel Tip: Leave the last day of vacation open in case any prior activities get cancelled. It didn’t work out for us for bio-bay kayaking, but it did for seeing Old San Juan’s castles, shops, and beaches!)
We hop out of the Uber, and like a local, Cas ducks into Café Botánico just steps away. The rest of us follow behind, and I get excited at another opportunity to order coffee in Español.
The barista expects me to order in English, but with a smile on his face, he replies to my order in Spanish, “¿Para aquí o para llevar?” (“For here or to go?”). I revert to English, unfamiliar with this phrase, but the barista appreciates my attempt and helps me out.
Coffees in hand, we adventure through various artisan stores and gift shops found amongst the pastel-colored buildings. One shop hosts beautiful local art works and prints, another has a lady painting ceramic art pieces from behind the counter. The whole atmosphere of Old San Juan is very laid back, a refreshing break from the hustle and bustle culture often found in mainland USA.
We walk to the end of the street, reach a seawall, and spy the windmills of Casa Bacardi across the bay. Turning right, we walk a few blocks to find the famous, time-tested fortress. But on our way we see an old lady feeding a stray cat…
One cat turns into three. Three cats turn into seven cats – after that, there’s too many to count! There must’ve been 20 cats that just appeared out of thin air. I didn’t realize it until later, but we walked through the Parque de Los Gatos (Park of the Cats)!
Castillo San Felipe del Morro
One block further we find ourselves afoot the huge green lawn of the Castillo San Felipe Del Morro (Promontory Castle of Saint Philip). Construction of this massive fortress began in 1539, and expansion continued in phases until 1790.
We walk a couple hundred yards up to the admission booth and pay $10 to get in the castle. Wandering around, we marvel at the architecture and age of the oldest structure any of us have ever witnessed.
The electric blue water sharply contrasts against the dark grey stones, shedding new light on the ambiance and aesthetic of the time.
Nooks and crannies are found all throughout the fortress, and ballistics and cannonball attacks can still be found lodged in some of the walls!
Walking around the massive grounds, we imagine what an invasion might have looked like just a few hundred years ago — it wasn't a pretty picture!
With the fort explored and the sun at its peak, we’re ready to hit the beach. So we catch a short ride to nearby Balneario del Escambrón (Escambrón Beach).
Escambrón Beach
Exiting the Uber, we walk towards the sound of the ocean, finding Mayson and Paige already with a sandy spot beneath some palm trees.
The first thing we do is strip down and wade into the water to cool off from the hot morning. We’re standing still for only a few seconds until we see fish swimming all around us – big ones too! The glassy water reveals various shapes, sizes, and species, none of which I recognize.
I lay out my towel on the beach, eager to soak up the brilliant Caribbean sunshine while I still can. I try not to think about the dark, cold weather back home, instead focusing on the squawking parrots in the palm trees swaying overhead.
Despite the oppressive sun, I haven’t worn sunscreen all week – my homemade moisturizer has worked miracles, and my 15oz tub of coconut oil has hardly been touched.
I’d spend the rest of the day laying out at that beach, but it’s our last night — we still have to take our family picture!
The Family Picture
We make it back to the house in time to shower, dress in color-coordinating outfits, and walk 10 minutes to the beach – all before sunset!
Grounding ourselves in Puerto Rico one last time, we laugh and smile as all 16 of us crowd together and create core memories.
We hang out at the beach awhile, me and Ivan flying my drone around. But soon it gets dark, and stomachs are grumbling…
We walk to Pirilo Pizza Rustica for dinner, and we’re surprised for a third time as they seat all 16 of us at once at the same table! To have it happen not once, not twice, but three times — each time we needed it — is miraculous to me!
After dinner we spent the night cleaning and packing up, not too eager to get back to the cold weather.
Last Travel Tip
Thankfully everyone and everything made it back safely – except my coconut oil! Puerto Rico’s warm weather kept it soft, and TSA wouldn’t let me take it in my carry-on bag.
Travel Tip: Freeze coconut oil (and similar products) before flying so they’re solid!
Puerto Rico Group Trip Recap
Puerto Rico, although a territory of the US, maintains its own unique culture — the perfect blend of fast-paced Americanism and slow island life. My friends and I had an amazing time doing awesome things in Puerto Rico:
surfing(!)
Old San Juan
El Yunque tour
Bacardi Mixology class
Catamaran & snorkeling
and everything in-between!
PR didn’t just give us sunshine and rainbows – it gave us memories for us to keep for the rest of our lives.
Final Thoughts
Travel can (and will) change you! Every trip, no matter how big or small, offers a window to a brand new life. If you look closely, you’ll find:
Tension in body and mind releases, stress melts away
New experiences wire new neural connections, forcing new perspectives
Expanded awareness promotes clarity of purpose, prompting re-evaluation of daily life
I often return from trips realizing that I’m taking life too seriously. The “important things” dissolve in significance and priorities are scrambled. It doesn’t always look pretty (usually taking the form of a mental breakdown), but it’s required to create and build from a fresh, grounded perspective.
To me, travel isn’t an expense – it’s an investment in a new mindset, expanded awareness, and heightened spiritual development — and I’m grateful to share my experiences with you!
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