With a 3.5 hour booked layover in San Juan there wasn’t a whole lot of time to see much of the city. The fact that the layover I booked was from 2:30 to 6:00 in the morning made it even more difficult. My initial plan was to just sleep in the airport. After all, I would be going to work directly from the airport and I wanted to be somewhat coherent. Instead, however, I listened to the little voice on my other shoulder and decided to take a tour of town instead.
Upon arrival I was first out the door and into the taxi line. I was actually seated in the cab briefly until the driver heard I wanted a 2 hour tour. Apparently that is rather uncommon for the 2:30am arriving flights and the driver was hoping for a quick fare and then to go home and sleep. Actually, it seems that most of the drivers were searching for a similar fare. Indeed, it took until the fifth driver until the dispatcher was able to find someone willing to stay up late with me and show me around. But I did get a driver eventually and we set off on a grand, middle of the night adventure to see Old San Juan under the light of the full moon.
The moon was bright on Monday morning. It was a beautiful full moon. And I needn’t have worried about seeing the sights as they are actually quite well lighted on their own. And they are rather magnificent to see in the quiet of the night. The forts loom large over the coast line of Old San Juan.
First stop on the tour was Fort San Cristobal. It was completed in 1797 and was actually still in use in World War II. Among other features, it has a huge ramp leading up to some massive entry doors. Quite impressive. As it was 3am the doors were locked, but that didn’t stop me from wandering around on the ramparts and snapping a few photos.

Next up was the Fort San Felipe del Morro. The El Morro fort sits out on the very tip of Old San Juan Island, jutting out into the Atlantic Ocean. The site has been a defensive stronghold for almost 500 years, though the current structure mostly dates from the 18th and 19th centuries. El Morro is even more impressive than the San Cristobal structure. In addition to the enormous walls (18 feet thick in some places) the fort also features a lighthouse (though not the original one; that was replaced in 1908 by the US military). The fort covers six levels and rises hundreds of feet from the surf below. It is rather amazing.
And while I’m very much looking forward to getting back to San Juan to see the sights during the day when we can actually go inside, I’m also very happy I got to see them at night. They are very well lighted and I was completely comfortable wandering around in the field in front of El Morro, even at 3:30 in the morning. There were a few other late night revelers out and about but not too many. It was actually quite nice to see it quiet.
And then I crawled back up into the taxi and we headed off for the airport. It wasn’t quite time for the tour to have to end but I was exhausted and the driver was, too. He dropped me off back at the terminal and, at ~4:30am, headed home himself to get some sleep.
As for me, I settled into a chair in the corner by the jetBlue gates and simply relaxed. No sleep, really, but I was able to rest quite nicely. Finally, shortly before 6am I was happily ensconced in seat 3F for the return flight to JFK. The sun was coming up outside and I was quite happy to put on my eye-mask and fall right asleep. I actually slept through the safety demo and takeoff. A short 3:25 later we were back in NYC and my jetting adventures were over. But not without a great last stop and tour.
