Read time: about 2 minutes.  Published 2025-09-01

In June 2011, we had been dating for just over nine months when we took our first big vacation together — joined by close friends and family. In all, there were eight of us: the two of us, another couple Adam has known since just after high school, their two daughters, the husband’s younger brother, and their mom.

We booked multiple rooms at Caleta 64 Apartments (sadly “Permanently Closed” as of this writing) and looked forward to beach time, visiting historic forts, soaking up the culture, and — of course — the food. Unfortunately, for one member of our group, the fun ended before it began.

The younger brother experienced medical issues from the pressurized cabin during the flight to Puerto Rico and was hospitalized soon after landing. He needed surgery and spent the entire trip in the hospital (he’s fine now). Unable to fly again, he even had to book a cruise ship to get back home. It was the first of many moments over the years that reminded us why travel insurance is so important.

The rest of the trip was unforgettable. Old San Juan is beautiful and wonderfully walkable — in fact, I highly recommend you do not try to drive there. The extremely narrow streets are best navigated by locals who know them well.

Each morning, we walked to a local café for coffee before heading out — sometimes to the beach for sand and sun, sometimes to explore one of the impressive forts, and other times to wander the shops and take in the colorful scenery. The food was amazing, and everyone we met was incredibly friendly.

One highlight was visiting the birthplace of the piña colada. I’ve always loved a good piña colada, but the original was the best I’ve ever had — so good that it spoiled all others for me!

On our final evening, we took a van to Las Croabas on Puerto Rico’s east coast, about an hour and a half from Old San Juan. There, we climbed into kayaks and paddled downstream to Laguna Granda, home to bioluminescent phytoplankton — microscopic algae that glow when disturbed. We arrived shortly before sunset, and by the time we reached the lagoon, it was dark. Each paddle stroke made the water shimmer, and we could trail our fingers through the surface to watch the glow swirl around them. It was magical — truly one of the highlights of the entire trip.

I would love to return to Old San Juan someday. We all have such fond memories of this incredible destination, and it truly marked the beginning of our love of travel together.