I never thought I would be the kind of person to enjoy a cruise. I used to do a lot of backpacking. I would arrive in a place, without lodging reservations, and using a guidebook would find a place. I would do a lot of research beforehand, but if I arrived in a place and managed to see all I wanted in a day, I would move on, even if I had initially planned for more time. I might also arrive and find the planned one day was insufficient and stay longer. I liked getting off the beaten track and exploring. I still do. And though I rarely travel solo these days as I have my daughter with me, I was still unconvinced about cruises. However, two summers ago, C and I joined our friends CZ and Little CZ for a Norwegian fjord cruise and enjoyed it.

For December 2024, I wanted to go somewhere warm on vacation with activities and sights for my older self and my pre-teen daughter and not involve a lot of planning. A cruise seemed the ticket.

We flew out of Washington, D.C. to San Juan, Puerto Rico, on the Friday evening before the Saturday 8 PM sailing. This made me a bit nervous given we would fly in winter when I thought more weather incidents could delay a flight, and I felt even more so when our Puerto Rico-bound flight changed at least five times before the day. In the end though, we made it, and right on time.

We landed just after midnight, so we stayed the night at the hotel right next to the Luis Munoz Marin Airport; it was a wee bit worse for wear, but it was close, clean, and we slept pretty well.

We checked out of the hotel the next morning and headed to Old San Juan in an Uber. Our boarding time was at 3 PM, so we had a few hours to sightsee. I had found a service online that would allow us to book left luggage service at an Old San Juan hotel even though we were not staying there. We dropped off the bags and then were off.

Our first stop was the Castillo San Cristobal, the sprawling ruined fortress on the northeast corner of Old San Juan. Constructed from 1634 until 1765, it is considered the largest European fortification in the Americas. Despite most of the space being only low-lying stone foundations and grass, its size still means it could take a very interested person a couple of hours to see it. C and I did not have that much time. It was also quite warm and C would not have tolerated spending too much time poking about. Given its historic and cultural importance, I am glad we had some time there. The weather was spectacular and so was the view across the small San Juan Island where the oldest part of the city lies. We could even see our cruise ship docked at the Old San Juan port from the higher ramparts of the Castillo San Cristobal.

After the Castillo, C and I took another two hours to meander the narrow streets of the old city. We popped into souvenir shops (for C) and I took photos. Then it was time to pick up our luggage and head to the ship.

In the evening, the cruise ship passengers were treated to an up-front-and-center view of the Club Nautico de San Juan’s Xmas Boat Parade. Started in 2009, the parade of festively decorated boats and yachts happens each year on the second Saturday in December. What luck that our cruise ship sat smack in the middle of the parade route in San Juan Bay! The spectacle has become a major event on the Christmas calendar, drawing visitors from across the island and further afield. Not far from our ship Amazon founder Jeff Bezos’ super yacht and support vessel were moored to also watch the parade. Though I tried, I could not get C to come up on deck to watch the parade, but I enjoyed it.

We were having a late dinner as the ship slipped out of San Juan port, the movement almost imperceptible. C and I took our anti-motion sickness pills–a lesson from our last cruise–and went to bed early. Exhausted by the late arrival the day before, a half day of sightseeing in the heat of San Juan, and the excitement of boarding the cruise, we both drifted off quickly. I had one of my best nights of sleep in a long while.

We woke up the next morning, the first of the cruise, to the beautiful view of the cruise harbor of Sint Maarten. The island is the world’s smallest landmass shared by two nations, France and the Netherlands, and it has been peacefully divided between them since 1648!

I visited Sint Maarten/Saint Martin for six days in early January 2009. I based myself in the small beachside capital of Marigot, on the French side of the island in an inexpensive guesthouse not far from the marina. Unfortunately, I do not remember much from the trip, nor did I write much down about it. What I recall is a rude waiter (ah, so very Paris-like), taking a very sweaty walk through the Dutch capital of Philipsburg, and taking a mini bus from Marigot to Grand Case.

For our excursion, I chose an open-top double-decker bus tour that would take us to both sides of the island. My daughter, like me, enjoys soaking in a place, and it was important to her to see both the French and Dutch sides. I had high, though still tempered, hopes for this tour. I should have lowered them considerably.

We met in the ship’s theater to be given wrist bands and then herded into groups that we met again in clumps on the dock. There a tour guide walked us, very, very slowly, to the bus. Once on the bus, one of our fellow passengers decided this was the best time to use the facilities, and we waited once more. Then the bus was off for a leisurely drive through Philipsburg to the border between the two sides. I do think the monument marking the division is pretty cool. Too bad we were not let off the bus. Our guide gave us some information along the way – some of it interesting (some say the point of division was decided by having one Dutchman and one Frenchman start walking from each side; the Dutchman was a bit drunk, which is why he did not get as far and why the French side is larger), some not at all (“if you look to the side you will see houses of different sizes” – I certainly don’t need someone pointing that out to me).

The bus made its first stop at Marigot’s Harbor. We had only 20 minutes there. Annoyingly, the tour guide pointed out the well-preserved ruins of Fort St. Louis on the hill overlooking the bay and said walking up made a great hike and did not take long. Except it took far too long for people who, stupidly, had only 20 minutes there. C wanted a French pastry, so we entered a patisserie. And, in stereotypical French fashion, we were ignored for a full 10 minutes despite my attempts to call out for service. With selection and purchase, we were left with five minutes to explore… Back on the bus, our next stop was… back on the Dutch side. That was it for the French part of the island!! I recalled why I generally loathe organized bus tours, and my expectations plummeted.

Our next stop was Maho Beach, a thin strip of sand directly behind the runway at the Princess Juliana International Airport, that has become famous for the photos of massive jets hovering over the beach just before landing. The thing is: A. we had all of 15 minutes at the site and B. the guide said the jets all arrive in the afternoon, and here we were standing about in the late morning waiting for absolutely nothing. Nearly all of us tour bus passengers stopped at the mini-mart for a treat, lord knew we needed something to pick us up, as we clomped back, sweaty and disappointed to the bus.

We headed back to Philipsburg, looping past the airport for dry, recorded commentary on the arrivals to the island and the pelican statue, then stopping briefly at an overlook (from where the overgrowth obstructed the view) before our last two scheduled stops: rum and cheese shops. I had mostly accepted the reality of this bus tour back in Marigot, but still chafed that the longest stops were commercial. Sigh. Though, as we dutifully filed our way into the Old Amsterdam Cheese Shop, I informed our guides we would not head back to the ship with them. We would be doing a bit of sightseeing and then heading back on our own.

We ditched the rest of the group, crowded into the shop, their arms full of truckles of gouda and edam cheese and bottles of liquor, and headed into the town. Well, town might be a bit strong, as it is four long streets divided by perhaps a dozen perpendicular and a population of less than 2,000.

I had remembered it differently. My memories were dim, but it had been of a more interesting place. Maybe it had been? There did not seem much local character; the shops were mostly souvenirs – cheap sundresses, t-shirts, magnets, crafts made with shells – mixed with Duty Free brand, liquor, and tobacco stores and micro casinos. The highlight was the cute Sint Maarten Court House decked out for Christmas. We gave up. We had given it a go, walked about on our own, seen a bit on our terms. Hot and sweaty, we walked the 20 minutes back to the cruise ship.

Back on the ship, ensconced in the warm temperatures, beneath an azure sky, and looking out on the turquoise waters touching Saint Martin, I was surprised to find I felt happy. Sure, it had not been what I had hoped for but we were after all on a Caribbean cruise! I looked forward to the next stop.