Old San Juan


Fresh air and sunshine! After a great night at my parents’ house in Beloit and a chilly 5:30AM drive to ORD, we arrived in Puerto Rico. Such a strange feeling to see the snow out the airplane window and know you won’t feel winter’s bite again this season.

Adios Winter!



We had a 24-hour layover in San Juan. Instead of staying in the crappy airport hotel, we rented a VERY cool apartment for less money (via TripAdvisor) in Old San Juan. It’s so great to stay in an actual house here in the old city. Our place was built over 200 years ago and has a vertical opening to the sky in the center of the building (“Zaguan”?) to bring in the cool ocean breeze. It’s what you did for air conditioning before there was air conditioning! And those of you who know the McGuire’s, know we hate air conditioning 🙂

View from our bedroom window to the building entrance.



Nature’s Air Conditioning (vertical column in middle of building to bring in ocean breeze)


If you haven’t been to old San Juan, I would highly recommend it. It’s a walled city, designed by the Spanish back in the 1500’s to repel other European countries (and their privateers) from establishing a strategic foothold on Puerto Rico. From here, Spain tried to close off the Caribbean Sea from the other European powers that sought the riches of Central and South America. Think of this place as the first tollbooth in the Age of Exploration.

Our flight to Dominica departed from San Juan at 2:50pm on Saturday, so we spent the morning walking around the old city and touring the two major forts that were built inside the city walls. It feels very much like being in an old city in Spain. Cobblestones, narrow streets, old architecture.

We toured the forts (Jimmy’s first homework assignment). Amazing to think about them being constructed. Of the men that died here, each wearing a type of colored sash to identify their country and intentions. Warfare must have happened so slowly then from our modern perspective. Ships are spotted, hours pass, cannons fire when in range, men march and climb in waves of humanity.  Hours of waiting and then chaos.  The Spanish managed to hold the fort (with a brief occupation by the English that was ultimately repelled by dysentery) for over three centuries until we showed up with a few battleships in 1898. It was really, really cool to see the evolution of military strategy and tactics played out in the design of the forts. I could spend several days here, but we had about three hours.

Plaza de Armas de San Cristobal


This place was not built for Shaquille O’Neal


Dungeon Graffiti (A Spanish captain doodled this awaiting execution)


Four Centuries of Military Technology (17th Century Guard Tower versus WWII Pillbox)


Next stop, Dominica!



3 thoughts on “Old San Juan

  1. Fascinating stuff, Mark! Glad things are off to a good start. I’m excited to follow along vicariously on this great adventure of yours!

  2. I’m going to love watching this adventure unravel!! You guys are so fortunate to be able to share this experience together as a family. SO envious!!

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