I’m in Puerto Rico for a few days chasing down a 1986 Grand Banks 42 Classic that’s up for sale here. If you caught the previous post, you already know the backstory.
My travel day started before the world was even awake—3:00 a.m., with no sun in sight and far too little sleep from the night before. By 3:30, Sylwia and I were already on the road to the airport. Thankfully, the boys had stayed with Babcia, which made the early morning shuffle a lot easier.
Check-in was quick, security was painless, and before I knew it I was boarding my four-and-a-half-hour direct Spirit flight to San Juan. Puerto Rico’s capital and its largest city is on the north side of the island, but the marina where the boat is docked is way down south, about forty miles away. For $100 I managed to get a cab willing to make the trip—long, but straightforward.
During the ride, I started scouting places to stay for the night. The plan was to meet the broker at 10 a.m. the next morning, so I wanted something within walking distance of the marina. The nearby hotels, however, were asking ridiculous rates, so I ended up booking a small condo right on the ocean. It wasn’t cheap, but it beat the hotel prices. Check-in wasn’t until 3:00 p.m., but the manager kindly worked it out by sending his son over with a key so I could settle in early.
Once I dropped my bag, the search for food and water began. Without a car, life on this part of the island is tricky. The sun was blazing, but I set off on foot anyway. Eventually, I found a spot where I filled up on a burger, tater tots, and some ceviche before heading back to the condo.
It didn’t take long for me to realize that this wasn’t the place to spend more than one night. There was absolutely nothing to do within walking distance, and the beaches were covered in algae—ugly, inaccessible, and uninviting. So I canceled my second night and rebooked closer to San Juan, right on a beautiful beach and within walking distance of downtown. That felt like a much better plan.
Later that evening, I walked over to the marina just to get familiar with the place and maybe catch a glimpse of the boat. I found the marina easily, but no sign of the Grand Banks yet. On my way back, I stopped by a mall to grab some food, drinks, and a little treat. To my surprise, they actually had my favorite ice cream—Haagen-Dazs strawberry. To my greater surprise, the pint was over $11. Back in the States, the same one is $3.50 at Walmart. Yikes. It was a late night as I continued to update our website.
On the second day after meeting with the broker and checking out the 1986 Grand Banks 42' Classic I went back to the condo, grabbed my bag, checked out, and started the long process of finding a ride back to San Juan. Taxis weren’t easy to come by, but eventually I connected with Cesar, who drove all the way down to pick me up. While waiting, I managed a quick breakfast of tacos and some wings and fries to-go.
The ride back was smooth, and Cesar filled the time by pointing out places on the map and recommending I check out Old San Juan. My hotel was right on the beach — nothing fancy, but in a great location. After checking in, I wandered down the street to Kasalta, a bakery famous for its sandwiches and sweets (and apparently a stop for Barack Obama back in 2011). Later, I caught an Uber to Old San Juan and wandered through its colorful streets, including the well-known Calle de San Sebastián, until my watch buzzed past 17,000 steps.
I ended the night at a tiny spot called Birra and Empanadas — simple menu, just empanadas and drinks. A few cocktails later, I crossed the street to Drunken Cookies for dessert before heading back to crash. It had been a long but rewarding day, full of first impressions and the spark of possibility.
Day three was my final day here. My flight wasn’t until 7:40 p.m., which gave me nearly the whole day to explore San Juan before heading home. I slept in until about 9, then spent an hour at the beach before returning to pack up and check out at 11. Breakfast was back at Kasalta, where I had a steak sandwich with shrimp salad—definitely hit the spot.
With time to kill, I grabbed an Uber to Old San Juan again, starting this time on the southern side near La Fortaleza, the official residence of the Governor of Puerto Rico. Just steps away was the iconic San Juan Gate (Puerta de San Juan), a historic entryway into the city. From there, I strolled past the Catedral de San Juan Bautista, one of the oldest cathedrals in the Americas, and paused briefly at Parque de las Palomas, known for its flocks of pigeons.
I then made my way to Barrachina, the restaurant that claims to be the birthplace of the piña colada in the 1960s. I couldn’t pass up trying one. Drink in hand, I continued west toward Plaza Colón, home to a Christopher Columbus monument, before looping back toward El Morro along the scenic coastal path I had walked the day before.
On the way, I ducked into a couple of small museum exhibits—not so much for the displays, but for the air conditioning. The humidity combined with my heavy backpack was brutal, and I was drenched in sweat by the time I reached El Morro. After a quick walk through the fortress—a UNESCO World Heritage Site with a $10 entrance fee—I called an Uber and headed to the airport for my late-night flight home. By then, my watch showed nearly 16,000 steps. The boys spent another night at Babcia’s, and Sylwia picked me up just before midnight.
A quick trip, but a great one. Puerto Rico left me with plenty of good memories—and maybe even a glimpse of what life could look like here someday.
