San Juan


On our way to a beach vacation in the Caribbean we arranged a one day layover in San Juan, Puerto Rico. Rather than stay at a drab airport hotel or a beach-and-casino mega-resort, we opted to stay in Old San Juan. It turned out to be a great decision.

San Juan began its life as the first Spanish outpost on Puerto Rico not long after Columbus first “discovered” the island. Actually, the entire island was originally named “San Juan” and the city was called “Puerto Rico,” but some mapmaker mixed up the names and they stuck.

To protect themselves from the natives they were agressively wiping out – and from other European powers pushing into the area – the Spanish built San Juan with defense in mind. It’s set on a hill that’s almost entirely surrounded by water and protected by high, thick stone walls and a series of forts.


Behind all the battlements they built what I imagine to be a typical Spanish city at that time: narrow streets, stone buildings, and shady plazas. Wrought iron streetlights, shuttered windows, and cheerful pastel colors provide extra Iberian flair. The whole thing is terribly atmospheric and is pleasantly unlike anywhere else I’ve been – at least on US soil.


We stayed at a hotel that had more character than any other hotel I can think of: Hotel El Convento. Set in a former convent on the same plaza as the city’s main cathedral, it oozes Old World Charm (and I don’t mean the euphemistic version of that phrase that realtors are fond of).

Many people use San Juan as a transfer airport to get to other places in the Caribbean. I’d highly recommend staying for a day or two instead. Head to the old town, wander around for a while, and enjoy what must be one of America’s most unique and interesting cities – not to mention it’s oldest.

See all our San Juan pictures on flickr.





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