For those who follow this blog (hi, Mom), you might remember my post from January 2020. Weeks before the COVID pandemic changed the world, Andrew, myself and a few others set off on the adventure of a lifetime. It was a trip of firsts: my first time in the Caribbean and my first nights sleeping on a boat. We were blissfully naive, living in a world before global pandemics and before LLMs. I even bought an underwater camera for the occasion, which broke immediately upon my return. The anchorages were unbelievable and the trip in 2020 was spectacular. We called that trip Pura Vida, which was the name of the boat we chartered. The Costa Rican expression means "simple life" -- no stress, no worries. It fit perfectly.
In 2026, we decided to do it all over again. We returned to the same marina in the Spanish Virgin Islands with a similar crew, but a different vessel: Fine Girl, a Lagoon 42 catamaran. It was my first time sailing on a cat, and the journey did not disappoint.
These are the adventures of our week at sea.
Day 0 – Saturday - January 31st
The transportation that Andrew had arranged via the Marina took us from the airport to the same Marina in Fajardo from which we had departed in 2020, stopping at Ralph's Warehouse for provisions - also the same store where we had provisioned before. The color of the transportation (a white van) was important because - and this is where Roman, Sergey's son steps into the adventure, had told him a joke a few days before - What are a kidnappers's favorite shoes? White Vans. So the joke of course came up both on the arrangements on the way to the marina and then on our way back. Our driver helped fit everything into the massive van, a stark difference from the tiny car we had rented in 2020 where we could barely fit our bags, let alone all the water and food. Once at the marina, we used Marina-provided carts to move all the gear onto the boat, which meant we were done in record time. Pura Vida!
The Fine Girl felt massive, when compared to the monohulls we normally sail. As we filled the cubbies and chose from among our 3 "luxurious" cabins and 3 freshwater "heads" equipped with electric flushing, I wondered how it would feel to handle a vessel this size. The boat included a hardtop bimini that offered really nice relief from both the sun and the rain that we'd later face. It also had multiple lounging spaces both in the cockpit and the salon, all with proper water proof cushioning, as is common with these chartering boats.
The Fine Girl felt massive, when compared to the monohulls we normally sail.
As we planned on heading for dinner, it began raining heavily, but the restaurant, even though it was outdoors, had protection from the rain, so we didn't care. Pura Vida. The evening included live music and good food. Off to a great start!
The waitress at the restaurant spoke only Spanish, so I tried to order arepas para todos (for everyone). She asked how many; I told her "para todos," she said they were big, so I assumed one order would be enough to share. After a long wait, she brought out a single arepa. It was definitely not enough "for everyone," but we had a good laugh and the rest of the meal was yummy.
The rain continued on and off, but the warmth was a welcome change from the blizzard that had hit Boston just days earlier. I was just glad the snow didn't cancel our flight. I was ready for anything. That night, I slept in the cockpit. Even though the hardtop stopped most of the rain, I still slept inside my bivvy – a sort of a water proof plastic "bag" with a "space-blanket lining" – with the sheets stuffed inside it. Sleeping inside the bivvy made it look like I was sleeping inside a giant trash bag (sounds cooler if we call it a space-blanket), but I didn't care, I'd missed sleeping outdoors.
Sleeping inside the bivvy made it look like I was sleeping inside a giant trash bag (sounds cooler if we call it a space-blanket)
Day 1 - Sunday - February 1st
On Sunday, we had our briefing with Jose from SailCaribe, who walked us through the various equipment of the Fine Girl, including the generator, AC, multiple fridges and freezers, and the water maker. We covered the precise ritual of the water maker – I had never been on a boat that could make its own fresh water, and it is kind of cool (albeit noise)! I knew we could "make" our own electricity with the generator and the motors, but with the ability to now make water too by desalinizing salt water, we would have complete autonomy for as long as the food (+rum) rations (+diesel) lasted.
First Sunrise and hanging out in the cabin while waiting for Jose
We made an uneventful exit at 11:20 AM, leaving the marina behind as we chased spots of sunshine among the rain. Behind us, the mountains of Puerto Rico were still semi-covered by clouds, but our focus was forward as we prepared to raise the mainsail. The electric winches made the work a breeze (pun intended), but the sail itself sat so high on the hardtop bimini that we had to climb onto the "roof" just to open the bag and maneuver the sail whenever it got caught on the lazy jacks on its way up the mast – which happened pretty much everytime we raised it…
From the cockpit, the mainsail was completely out of sight, which felt slightly off. I'm used to sailing monohulls, where we all normally face forward and the mainsail is right in the middle of our view—where we all feel like we're part of steering the boat even if we're just slacking around. But this catamaran layout made it easier for everyone in the cockpit to face backward, leaving the helmsperson in their station to steer while everyone else was just a passenger. I eventually walked over to the bow to lie on the trampoline, which felt like a lot more fun. That lasted until a rogue wave washed over me and I got soaked. I also thought the lack of heeling was weird; catamarans don't heel unless they are about to capsize, which would be truly bad news.
I walked over to the bow to lie on the trampoline. That lasted until a rogue wave washed over me and I got soaked.
Day 1 meditation: As the boat glided over the endless turquoise blue, my mind drifted to a completely different scale. My meditation that day was about electron microscopy (EM), where the scale of what you're trying to look at is so small that visible light waves are just too "fat", so you need to resort to electrons. Thanks to a connection Sergey facilitated with a colleague working on the science of looking at incredibly tiny things with EM, I found myself asking Gemini to explain how it all works and how EM can be used to look at living things without "frying" the sample with the fast pulses of electrons. It's funny what the brain latches onto when you aren't forcing it to think about anything in particular. There I was, surrounded by the vastness of a turquoise blue ocean, preoccupied with the mechanics of spying into the very small.
As we approached Culebra, our crossing for the day, the mountains faded in the distance, semi-covered by clouds. Soon, nothing else existed but the turquoise blue waters of the Caribbean and islands in the distance. The wind was spectacular for a crossing to Culebra, the sun came out and we were able to watch the sunset! Slowly the blue took over my mind, making the rest of the world—and the freezing Boston we had left behind—feel as distant as a bad dream.
The sun came out and we were able to watch the sunset
Giant Moon!
I slept outside again. By midnight I woke up, my brain latching onto the quiet—and the bug bites. I tried to keep my arm inside the bag, but I suspect that in my sleep it came back out and was a feast for the bugs. For some reason, I'm always the first to get bit (or at least the first to notice). I squeezed my arm back into the bag and put a sad playlist on my headphones. Evanescence started playing... The worst is over now and we can breathe again… Still unable to sleep, I saw the phone battery hit 20 percent. I forgot to put it on the charger. I slept on and off until I noticed the light slowly changing as the sun began to rise. A new day full of possibilities and adventure! Then, it started pouring again…
Day 2 - Monday - February 2nd
It was a slow and pleasant morning on anchor, with hints of a sunrise even though the rain clouds had returned. Our first morning in anchorage for the week. I had my coffee, but even with the caffeine, I was still just... slow. Caffeine usually makes me social, but that day the itchiness from the bug bites hijacked my attention. Even with the lidocaine and hydrocortisone, they were still itchy.
It was a slow and pleasant morninn
Then came the rain. Heavy rain—start, stop, start. I didn't really care; it was warm, and I was in the Caribbean. Besides, the hardtop bimini provided very good cover from the rain outdoors and we were able to eat the breakfast eggs that Lena G prepared. When it was finally time to pull the anchor up, I got drenched again, even through the "waterproof" jacket.
As Andrew steered, the rest of us hung out in the cockpit, protected from the rain (Andrew himself was not so he got drenched). Made some more tea, chasing that caffeine high, and watched the raindrops and the tiny rivers of water that formed and fell to the floor. Water was everywhere - above and below. It was beautiful – overcast, but lovely.
Day 2 meditation: As we motored through the rain, watching the water flow off the bimini, my mind drifted back to the end of Game of Thrones. I'd finished the last episode the night before we left—staying up until 11 PM even with a 5AM Uber pick to get to our flight to San Juan on time. It was worth it! I loved that Drogon melted the Iron Throne; it was as if he knew all along that the chair was the root of all "evil" in Daenerys's mind. If she had abandoned the illusion of being the Queen and worked through her trauma, she wouldn't have forced him to Dracarys his way through the destruction of King's Landing. The show isn't about good vs. evil. It's about accepting vulnerabilities, not hiding them. Something Daenerys was not capable of doing. To quote Tyrion: "Wear it like armor, and it can never be used to hurt you."
The rain stopped while we motored toward Cayo Luis Peña. It was our first (of many!) snorkel-worthy site – the water shifted through 3-4 shades of blue, and you could see the sand and coral through the water.
The water shifted through 3-4 shades of blue, and you could see the sand and coral through the water.
Below the surface, the reef was alive. I watched a large school of parrotfish gnawing on the coral while one tiny, territorial black fish tried to push them away; the parrotfish would drift off, if only to humor the tiny black fish, only to circle back a moment later. I spotted a few blue tang fish ("Dory"-fish if you've seen Finding Nemo), tigerfish, and the strange, geometric shape of a black-and-white boxfish. Sergey even found a giant sea urchin.
Below the surface, the reef was alive.
Once we all got back from our underwater exploration we had lunch and waited out another passing shower before raising the anchor. As we motored back to Ensenada Honda, where we would spend the second night, the rhythm of the boat finally caught up with me. I fell asleep in the cockpit, waking to the sound of Sergey calling out "Lena, it's time to drop the anchor."
Once we were settled at anchor, Andrew decided to experiment with the stand-up-paddleboard that Jose had left on our boat – he told us "you didn't order one, but I had nowhere else to put it", so we got a SUP for free which Andrew had fun using to explore the other boats around where we were anchored.
Andrew decided to experiment with the stand-up-paddleboard
Before nightfall, the others dinghied to town for supplies while Sergey and I stayed behind. We spent the afternoon piecing together a protective "sunbrella" cover he'd found on board—a literal jigsaw of separate pieces of fabric and zippers of different shapes and sizes. There were no instructions, no online tutorials, and no videos to guide us. We just had to guess our way through the configuration until the pieces finally clicked. It was fun!
Just as the others returned, a massive squall arrived. In the cockpit, we were perfectly shielded by the cabin—and so was a pigeon, it seems. The bird landed on our stern rail and resisted every attempt to shoo him off. None of us wanted to push or hurt him; we just tried to scare him away, but he wouldn't budge. He just hunkered down and refused to leave. When one of us finally tried to shoo him with a paddle, he simply moved to the other side of the dinghy and stayed there the whole night. We had to clean up pigeon dung the following morning. We don't mind a guest, but at least be a respectful one and don't poop all over our boat, please sir.
The bird landed on our stern rail and resisted every attempt to shoo him off.
Our comfort would have been very different had we chartered a monohull; instead, the boat barely moved with the waves thanks to the dual hull that catamarans are famous for! We sat comfortably outdoors, protected from the rain and the wind, listening to the howling sounds of 20–30 kt gusts while eating dinner and enjoying our rum. Pura Vida!
Day 3 - Tuesday - February 3rd
The rain and squalls were forecasted to continue and so they did. We had a quiet morning on anchor at Ensenada Honda, next to the dinghy dock – we weren't going anywhere in this weather. The anchor seems to be holding well. It was a good day for reading, hiking and socializing. The boat was large enough to let everyone do their thing, but even when space is tight, this gang vibes well together.
It was mid-morning when Andrew decided we needed to "make some water" using the boat's reverse osmosis watermaker. It's a huge drain on the batteries, so we had to run the generator. It was noisy, and we had to deal with the hum for a while, but once it was finished, our freshwater tanks were full. We needed a change of scenery, so we lowered the dinghy and headed into town. A few stayed behind. It felt good to stretch our legs; we hiked a bit and bought more drinking water—we don't drink from the tanks, as we never know what might be living in there. It was a day of water.
It was mid-morning when Andrew decided we needed to "make some water"
Lunch was at Mamacita's, right on the canal. It was good entertainment; giant fish lingered in the water for scraps, and the customers were happy to comply. We spent a good chunk of the afternoon on the island – good food, good friends, a few drinks, and a ton of rain. We went for another hike after lunch, we all felt we needed to stretch our legs.
Giant fish lingered in the water for scraps. Island views.
We spent the rest of the afternoon on the boat—reading, playing cards, just a relaxed evening. Everyone was in their own zone. The squalls and rain kept coming, along with heavy gusts, but the cockpit was so well-protected that we could play cards through 20-knot winds.
Then came the rum, followed by some political chat we probably shouldn't have had. Then, bedtime. The night brought dark dreams. I was in the cabin—comfortable enough, but my mental space was heavy. I "chatted" with Gemini about the political discussion we had had earlier, and it called me 'intellectually vain'. Fine. It might be right.
Day 4 - Wednesday - February 4th
We had another lazy morning at anchor in Enseada Honda. Rain and more rain, but with it came the rainbows – strong, vivid ones. We saw a rainbow over the dinghy dock, then it vanished, only to be replaced by another, and another. Eventually, a double rainbow appeared.
We saw a rainbow over the dinghy dock, then it vanished, only to be replaced by another, and another.
Neil spent some time droning in between the tropical downpours.
Neil spent some time droning in between the tropical downpours.
Then, finally, the sun came out. The clouds disappeared and the adventure started! I went to sit down in the bow by the trampoline to take in all of the sun. We made a short trip first – motor only. We went around to Punta Soldado for more snorkeling. Saw more fish, more coral. Then, we hauled anchor for a very important mission: we had to go 3 miles offshore to dump the holding tanks. It's the unwritten rule of the sea – you can have the turquoise water and the tropical sun, but first, you have to deal with the waste and that can only be done far away from the beautiful reefs.
Saw more fish, more coral.
The "dirty work" done, we found a cove with reefs and grabbed one of only two mooring balls. We took the dinghy to shore for a walk – we wanted to go to Flamenco Beach, often ranked among the best in the US. The reality was less idyllic: the wind was howling and the surf was hitting so hard the beach was officially closed.
The wind was howling and the surf was hitting so hard the beach was officially closed
We had to hike a mile across the island to get to Flamenco Beach. Back at the cove where we moored, we had left the dinghy secured with an anchor tied around a tree, but Ben – who stayed on the big boat – didn't know that. From his vantage point, the dinghy looked like it was drifting. He called us after the one mile walk, saying it had turned completely sideways. We had another mile to go before we could rescue our dinghy.
Flying over the reef
Sergey had his own adventure while we were gone. He opted for snorkeling instead of the hike and ended up getting dragged by a strong current and having to climb up some rocks to rescue himself.
By the time we all reconvened, the drama had settled into a gorgeous night. The sky was full of stars! So many stars that I could barely make out Orion's belt. I laid down on the roof for a while doing nothing but staring at the stars. At some point I looked at the water and noticed some specks of light in the water too. Reflection? No! It was bioluminescence! Stars above and stars below! Andrew went for a night swim with the little single celled creatures.
Day 5 - Thursday - February 5th
The sound of heavy rain drumming against our Fine Girl persisted through the night, but by morning, the clouds finally gave way to a radiant, golden sunset. It turned into one of those perfectly balanced tropical mornings: a refreshing sunrise snorkel followed by a slow breakfast and a few chapters of my book. I even managed to tune into an earnings call, though I'll admit my focus was wavering in the serene setting. Who wants to hear about GAAP and non-GAAP earnings when there are coral to explore and colorful fish to follow!
The clouds finally gave way to a radiant, golden sunset.
My focus was wavering ... who wants to hear about GAAP earnings when there are coral to explore and fish to follow
The snorkeling and sun bathing were spectacular, but the local insect population proved to be a far more formidable opponent than I had hoped for. Despite the heat, I reached a breaking point in the "bug meter" where I had to abandon my swimsuit for the protection of full-length pants and full length-sleeves… Sigh.. I threw everything I had at them—bug spray, oils, skin barriers—but these bugs were utterly relentless and completely unimpressed by my chemical warfare. No-see-ums, our floridian friends call them. They seem to have a particularly strong liking for my skin.
The snorkeling and sun bathing were spectacular..I reached a breaking point in the "bug meter" where I had to abandon my swimsuit for the protection of full-length pants and full length-sleevs
Andrew announced that the plans we made for our next passage: we would go to Vieques! We grabbed a quick bite for lunch and got moving. I spent most of the passage in the sun, catching up on plenty of reading before the library loan expired. The digital library "ticking clock" adds a whole new level of stakes to the journey. I could easily just buy the books I read, but there is something so much more exciting about that two-week deadline for the automatic eBook return. It turns every chapter into a race against time: Will I make it to the end? Or will I be stuck waiting three weeks (or months!) to finish the final pages because the library ran out of digital copies?
Andrew announced we would go to Vieques.
The midday passage had its share of small hurdles—the kind of "little annoyances" that test your zen on a boat. With most of our outdoor seats still wet from the rain, finding a comfortable and dry nook in the sun was becoming a mission. I was using my rain jacket as a makeshift pillow when I raised my head to look at something and what I saw was my jacket flying away and into the ocean. Oh well. It became my donation to the sea gods.
I think this was the first time I noticed how this boat's design makes the type of shared sailing we're used to on a passage a harder mission to accomplish. The helmsman station was built for a small crew of two or three to handle everything, while the rest of us are sleeping or attached to our electronic devices, which means there's no real sense of "all hands on deck" when it's time to prepare to tack. It's a strange feeling being so disconnected from the mechanics of the sail. I couldn't even tell where the wind was coming from or why we'd shifted to motoring instead of sailing. Answers to questions like why we didn't take the other side of the island remain out of reach. All the planning and tactical conversations happen at the helmsman station, and there isn't enough room for all of us to be part of the huddle. It turns the passage into a bit of a mystery for those of us not at the wheel.
This boat's design makes the shared sailing a harder mission. The rest of us are sleeping or attached to our electronic devices.
The passage ended at Punta Arenas, a place with a special meaning for us as it was the very first stop we made when we came to fall in love with Puerto Rico for the first time on our previous charter in 2020 on a boat called Pura Vida. There was no provisioning at this wild anchorage, which meant no rum, and we were very close to running out. We probably should have bought more in Culebra, but in the end, it didn't matter—being back to this lovely anchorage was enough.
The passage ended at Punta Arenas, a place with a special meaning for us.
Sunset did not disappoint! We kept our eyes on the horizon, soaking it in for as long as we could. As night fell, we turned our attention upward, searching for the first signs of the stars in the night sky. We settled in for dinner and polished off the last of the rum, eventually noticing some massive fish circling in the water near our boat. Later on, the clouds finally cleared, and the stars came out. I spent a long time just staring up at them. Pretending this was my life now… Tempted to "accidentally" miss that flight back to Boston on Sunday.
Sunset did not disappoint! We kept our eyes on the horizon, soaking it in for as long as we could.
Vieques Passage Meditation: Without that shared effort to ground me, there was nothing to break the cycle of mindless distractions I tend to come up with during these long stretches at sea. I ended up spending the time reading, taking notes about the voyage, and just hanging out in the sun. I stared out at the water, watching the islands crawl by, and found myself wondering: What if this is my life forever? Could I decide, like the character in my book, that I did not want to be bound by the decisions I made 13 years ago when I decided to move to Boston, and just never leave?
My thoughts drifted to the cycle of body shaming I fall into every time I see a picture of myself. I remembered those extreme calorie restrictions—600 or 700 a day—which gave me a false sense of power and mind over matter, but only served to slow my metabolism until "normal" eating meant weight gain. Recently, the rise of GLP-1s like Zepbound has shifted my perspective. I've started seeing weight through a medical lens—as a biological missing piece rather than the failure of character that way too many people still believe it is. That shift is what finally helped me accept how I look and feel less self-conscious. Now, I'm just waiting for the market to be flooded with GLP-1 agonists and prices to drop. Hopefully soon.
Day 6 - Friday - February 6th
My dreams weren't too dark that night, which is always a relief, and the sunrise was spectacular but by breakfast, that familiar itch from the bug bites had already set in. I managed to sneak away from my seat and change quickly for a swim. At least while swimming the itchiness seemed to go away for a bit. The water was a bit murky with not much to see, but it felt good to move. Afterward, I let myself dry off on the front deck, and we just stayed there, soaking it in until lunch. Once we'd eaten, we pulled up the anchor and moved further along the coast of the island.
The sunrise was spectacular
We then headed over to Ensenada Sun Bay. Andrew put me at the helm for this stretch, having me be the one controlling the helm while we lifted the anchor and then dropped it again in our new spot. It was a beautiful, paradise-looking place – totally picture-worthy. Once we were settled, we jumped back in the water to swim and spend some time looking for colorful fish to stalk.
Andrew put me at the helm for this stretch
Neil had some great luck with the drone – he went up scouting for the local wild horses which apparently are abundant in Vieques and he actually spotted them! After that excitement, we lifted anchor again to go check out the mooring field nearby. It was a nice area, but it turned out to be incredibly shallow. I didn't see the depth sounder myself, but Andrew claimed we were in less than four feet of water. He moved away quickly and managed to avoid any trouble, but it was a definite cautionary tale about how fast the depth can disappear.
Neil had some great luck with the drone – he went up scouting for the local wild horses and found them
After another swim, we motored over to Esperanza, the main town in Vieques. The plan for the evening was solid: provisioning, dinner, a tour of the bioluminescent Mosquito Bay, and then observing the Sabbath back on the boat.
But the conditions were wavy, and the transition from the boat to the dinghy didn't go smoothly. I slipped, straining both my ankle and my knee in the process. It was hot – at last hot! – as we dropped Sergey off near the beach for some snorkeling and continued toward the dinghy dock.
I remembered the dock in Esperanza being a challenge from back in 2020, and it lived up to its reputation. The platform sat a good 4 to 5 feet above the dinghy. I tried to use a tire as a step to climb up, but I left one foot on the dinghy and one in the tire just as the dinghy drifted away. I was stuck until the guys – Ben and Neil – who had already managed to pull themselves up – managed to pull me up onto the platform. It worked, but it wasn't graceful!
The platform sat a good 4 to 5 feet above the dinghy.
Esperanza, the main town in Vieques
We made our way to Duffy's for lunch, but first, we hit the grocery store. We managed to find it quickly and grabbed the essentials: rum, beer, yogurt, grapes, and some ice cream. To save the ice cream from the heat, we sent Andrew back to the boat to drop off the groceries and pick up Sergey and Lena. At the restaurant, we had a mix of shade, sun, and a perfect breeze—it was really pleasant. As we sat there, we saw a single horse just casually walking down the street. At first, I assumed an owner must be nearby, but we later found out these are all wild horses that just roam the island. The food was incredibly fresh; I had a wedge salad with grilled wahoo that was delicious.
At the restaurant, we had a mix of shade, sun, and a perfect breeze
After dinner, we caught the sunset while I sat with some ice around my ankle – it really only started hurting and looking swollen after we left the restaurant. I asked the restaurant for some ice to try to bring the swelling down. Sergey regretted that he had left the duck tape, which had saved us on many occasions, on the boat. Would have been perfect to keep the ice in place! The horse that we had seen walk past was just hanging out, a wild horse just looking for company and maybe some food.
During sunset a wild horse came to town looking for some company.
We walked all of 6 minutes from the restaurant to the place where we were supposed to meet the Mosquito Bay tour guides. They handed out life jackets and loaded us onto an old yellow school bus. Then came the bus ride – and "wild" is the only way to describe it.. After a small trip on paved roads, the bus dived into these muddy, pothole – ridden roads, that just added to the adventure before the adventure! The bus was hitting branches left and right, the leaves slapping against the windows as if the forest was trying to reclaim the road.
They handed out life jackets and loaded us onto an old yellow school bus.
Mud and hole and mud and hole. It felt like that ride went on forever, but we finally reached the edge of the Bay. They split us all into groups of two, handed us paddles, and sent us on our merry way into the kayaks. It took me a minute to realize that the bottom of our kayak was actually glass.
As we paddled out into the center of the Bay, the water came alive—our paddles drew a fluorescent flow with every stroke. It was super cool. Beneath the kayak, electric sparks darted under us, creating streaks of light that moved toward our back like tiny shooting stars underwater. When we plunged our hands into the water, we could see the fluorescence cascading down, with a few lingering dots remaining on our skin for a few micro-seconds. It was so much fun. Some of the crew even spotted fish darting through the water, leaving glowing streaks of luminescence trailing behind them like underwater comets. I tried to take pictures but no luck, they all came out dark, you'll just have to imagine the water coming alive with every movement.
We tried to take pictures of the bioluminescent bay, but no luck; they all came out dark.
Then the adventure was over, and it was time to head back to town. Back into the school bus we went – once again tackling the mud and the holes and the tree branches. As we pulled back into the parking lot, the bus scared away two more horses that had been lingering in the dark. And just like that, the adventure was over. A new set of groups was already lined up, waiting for their turn to experience the glow.
The return to the dinghy at the dock was thankfully much easier than the climb up. We motored back to the catamaran, where Andrew opened his bottle of "pessimist" wine – and then a second one. I finally let the day's energy catch up with me and fell asleep on the bed in the cockpit. And just like that, the night was over.
Flying over the Vieques, looking for horses, scaring some birds.
Day 7 - Saturday - February 7th
The next day started off amazing – just pure, calm perfection and a gorgeous sunrise. Between the sunrise and the clouds reflecting off the glassy water, it was as peaceful as it gets. We really had our morning routine down by now: coffee, followed by breakfast - sometimes boiled eggs, other times cheese, bread, or avocado. Everything tastes better when you're in such a lovely anchorage.
We stayed in "lazy mode" for a while. Sergey headed off on a snorkeling adventure, but the rest of us just floated and bathed around the boat. It was the definition of a perfect morning in a paradise spot.
The next day started off amazing; we stayed in lazy mode for a while.
We decided to cast off and head back toward Punta Arenas for a bit. It turns out we weren't the only ones with that idea—there were a ton of boats and snorkelers already there. We hadn't really noticed the snorkeling scene before, but there were people everywhere that day. It was such a bright, sunny day, and that paradise beach up ahead was calling our names, so we lowered the dinghy and headed out to explore.
We decided to cast off and head back toward Punta Arenas for a bit. It turns out we weren't the only ones with that idea.
We beached the dinghy, swam for a while, and spotted a few fish. Eventually, we made our way to the other side of the beach where the divers were gathered. It was much more exciting over there – underwater canyons and coral formations where all the interesting life seems to hide. I saw fish after fish, and although a guy nearby mentioned seeing a turtle, I didn't manage to spot one myself.
Getting back onto the dinghy from the water was quite a task – definitely not an easy thing – and I needed the guys' help, Neil and Andrew, to pull me back in. Then, as Sergey was just about to jump back in, planning to use his flippers to propel himself at full speed, Andrew asked for his phone which was in the anchor compartment, causing me and Neil to open it just as Sergey propelled himself, and his head ended up flying straight into the opened compartment door! It was some seriously bad timing, but luckily no blood was drawn, and we all had a big laugh over it.
Sergey caught by the drone in one of his adventures.
Can't get over how gorgeous the view was from there.
Then Andrew drove us back to the big boat, and we settled in for a nice mix of beers, lunch, and tea. After that, it was time to get ready for a proximity cast off the following day – to avoid a big passage on Sunday morning, back to the marina to return our Fine Girl to Jose, we decided to spend the night on Isla Palominos, which is very close to Fajardo. We motored for a bit at the start, but the wind picked up enough that we could officially sail. I hung out on the roof with the guys for a while, but eventually, I retreated to the cockpit—it was just more comfortable down there, and it's where I had left my phone. The sky turned dark surprisingly fast. We'd already dumped our tanks and used the watermaker to top off our supply.
The sky turned dark surprisingly fast.
I went back to my book, though I did try to meditate for a little while first. I sat there looking out at the ocean, observing the white caps on the waves, feeling the flow of the water beneath us, and just watching the horizon. But eventually, the pull was too strong—my book was practically calling out, "Read me!"
After a few hours of alternating between sailing and motoring as the weather turned a somber grey, we finally made it to Isla Palominos. We had a couple of false starts trying to anchor and grab a mooring ball, which is always a bit stressful when you're tired.
We finally caught one that actually had a loop for our lines. It was a bit close to the shore and the shallow areas, but it felt well-protected. We used a docking line to secure it even further, and that felt solid for the night. The weather turned rainy and cold again, but luckily our cockpit was very protected, so we stayed dry and tucked away.
My mother used to say that if you pressed your ear against a seashell, you could hear the ocean. The ocean is calling.
We happily finished off the last of our rum and sat down to a dinner of spaghetti with leftover fish and veggies. As we ate, we watched the water – some big fish, which Sergey thought were sharks but later gemini helped us identify them as tarpon, were jumping all around to grab their prey. It was much better entertainment than an episode of Game of Thrones.
Some of the little fish seemed to be taunting them, swimming right at the surface. Every time a tarpon lunged for a meal, the little fish would hop over the water six or seven times, miraculously getting away. A few minutes later, those same little fish would be right back next to our boat, and the cycle of attack and escape would start all over again.
Some big fish were jumping all around our boat to grab their prey.
The night was uneventful otherwise; the mooring balls and our extra docking line held perfectly. I slept in the saloon, but it was a restless night. I kept waking up in a cycle: I'd get too hot and have to open the windows for a breeze, but since they open inward, the rain would eventually start blowing in. I'd wake up with raindrops on my face and have to scramble to shut the windows back up.
Reflections on The Maze and the Flight: While I was out there, trying to meditate against the rhythm of the waves, my mind kept drifting back to the book I was reading, the Maze Runner trilogy. I was on the third book, and the protagonist had spent the entire series desperate to recover the memories that were wiped before he was sent into the maze. But when he finally had the chance to get them back, he realized he didn't want them. He discovered hints that, as a prodigy child, he had actually helped design the very maze used to torture and test the other kids. Now that he had lived through the experience, he chose to leave those memories behind.
It made me think about my own life – specifically my decision to move to Boston thirteen years ago. That choice was made by a person I barely recognize now. At the time, I wasn't well – physically, emotionally, or financially. Boston was a "no-brainer"; it offered an escape and a new adventure, and it paid double what I was making. Plus, I've always seen Boston as my favorite European city outside of Europe.
But sitting there on the water, I realized that decisions made at one point in time don't have to bind us for life. I have the right to make new decisions based on who I am now, with everything I know today. For a moment, I let myself imagine: What if I "forgot" to get on the plane? What if I just decided to stay in San Juan?
Spoiler alert: I did get on the flight. But the realization itself was a breakthrough. I don't have to be a prisoner to the choices of the person I was thirteen years ago.
Day 8 - Sunday - February 8th
At 6:30 AM, I woke up and the morning routine began, though this time it was shaded with the color of departure. Instead of just the quiet rhythm of coffee and the sunrise, the tasks felt more final: packing my clothes back into my bag, preparing for a "real" shower at the marina, and checking into my flight back to Boston.
The transition back to "real life" happened fast. We picked up Jose at the fuel dock and with Jose's spectacularly maneuvering the giant around very small spaces, we arrived at the slip at precisely 10:00 AM. After the luxury of a long-awaited warm marina shower, we met the taxi Neil had arranged with "Tony" for 11:05.
The transition back to real life happened fast.
Tony and his driver took us into Old San Juan for one last meal. It was a good lunch, but the shift was jarring; the quiet, contemplative magic of the ocean was officially gone, replaced by the loud, bustling soundtrack of the city.
Nostalgia began to set in as we discussed how well the trip had gone; I suspect everyone was feeling that bittersweet pull. Before heading to the airport, it was time for the Ron del Barrilito tour that Neil booked for us to enjoy the island one last time before returning. Andrew and Lena had been there before and knew it was a good experience, so we made the stop. We started with opening cocktails and then moved into a tasting after learning about the history of the rum. It was a great tour – the guide was very entertaining and told the story so well that it really added color to the tasting.
Final Reflections
Getting to the airport was easy, and as I was sitting on the plane I picked up the phone to write these notes because I had just finished watching a movie about Bruce Springsteen – about his struggle with depression and how that period actually led to his most successful album. It left me wondering: Am I avoiding my best times? Or is it possible that my best times are already behind me? It's a heavy thought to carry back to Boston, but maybe it's part of the "new decisions" I'm allowed to make now. It's probably a conversation I need to have with my therapist. Bruce didn't look for numbness in drugs or alcohol; at least, that isn't the core of his story. He sat with it.
Curled up in the seat, I let my head go to that dark place, listening to my sad playlist – Evanescence, Sufjan Stevens, Sia. The questions just keep running through my mind: How is it that I slip into this mode so easily? One minute I'm on the ocean, and the next, I'm back here. But then I think about the need to force myself to remember the happy memories alongside the unhappy ones. I look back at this week with my friends; they really care about me, and I care about them. That connection shook me out of the numbness. It reminds me that even when the darkness feels easy to sink into, there is something real and vibrant that pulls me back out.
Back Home
Lying in bed before falling asleep, my body still expected movement that night – that gentle, persistent rocking of the waves. I woke up again at 6:30 AM, but this time to a sunrise over snow and the harsh sounds of the street. The era of deserted anchorages where we were the only boat is over. No more waking up to the sound of waves crashing against the shore... or the roosters. I can't complain too much about the sunrise – it's lovely when it hits my window and reflects in the snow – but it isn't warm, and there's no walking around the deck to overlook the mountains. Maybe that was the nostalgia setting in on the plane: the recognition that life could be like that, but it's a life far away from constant electricity and fresh running water. It's a beautiful dream, just a very different reality.
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