Tearing Up Old San Juan Essay

Fresh off of my journey to Old San Juan, here is my latest travel run-down. Aside from the obvious pluses Puerto Rico has to offer (you don’t need a passport if you’re a US citizen, direct flights are cheap, it’s always hot, and a beer costs a dollar or two), this is really a guide for those looking to do more than simply post up at a ritzy beachfront hotel. With this in mind I decided to dive into the streets of Old San Juan…here’s what I found.


We stayed at the Posada San Francisco Guest House, a family owned establishment catering mostly to young travelers exploring the Caribbean. This place is no Ritz, but the owners are overly friendly and the location simply can’t be beat. Overlooking Plaza Colon and San Juan harbor, this place is located in literally the single best spot in Old San Juan.

The guest house is on the top two floors of the tallest building in Plaza Colon, so you are overlooking the entire old city when sitting on the balcony — a huge plus in my book. You are close to everything, and are literally next door to Castillo de Cristobal, a old fort historically used to protect the city. Anything you could be looking for — beaches, restaurants, bars, shopping, casinos — it’s right there. In my opinion this is not a place to drag your girlfriend, but if you can deal with roughing it a bit this place is a straight bargain and is filled with lots of interesting people, who made our stay that much better.


It’s the Caribbean… San Juan is hot as hell, pretty much all the time. As far as the beaches go, I’m told we made a mistake in not hitting up Condado. We took a day trip to Isla Verde, where we were initially very happy with the beach until we were told that it was the worst beach in San Juan. If that’s the truth, Puerto Rico is doing pretty well for itself on the beach front. The beaches tend to have coarser, more yellowed sand than the typical “idyllic” beaches of the Caribbean.

We also hit up a strip of beach directly behind Castillo de Cristobal, about a 10 minute walk from our hotel. This was a rockier strip of beach, but a great place for a quick swim, until we realized that their were packs of gay men hiding every few hundred yards in the jungle beyond the beach. Apparently this little strip is a meeting spot for San Juan’s sketchiest, who use a series of whistling calls to beckon to one another. We did not return, and I suggest you steer clear as well, unless you’re looking for a romp in the bushes.


The food in Old San Juan was definitely one of the highlights of the trip. If you’re looking for a reasonably upscale place to get a fantastic meal, The Parrot Club is it. While the decor is relatively unremarkable, it’s the food and the service that will blow you away. I went with grilled plantain encrusted mahi mahi, served over a mound of mashed yucca with green beans and summer squash, then drizzled with beurre blanc. The mojito and the tropical fruit cobbler completed this hour of bliss. While it’s immediately obvious that Old San Juan is filled with great food, I’d go back to this place in a heartbeat.

The second of my food excursions of mention was The Blessed Cafe. I’ll categorize this as a place for someone looking for a more authentic Caribbean experience. This place is Jamaican (yes, in Puerto Rico) through and through, and is owned by a Jamaican mon who has brought his native cuisine to Puerto Rico. It feels like you are sitting in a bomb shelter, but the Jamaican decor, the owner of the place, and the soft reggae music make you surprisingly content. I had the garlic shrimp, served with steamed coconut rice, grilled plantain, and carrot, along with a side of coco bread. To drink? Red Stripe of course (we’ll touch on Puerto Rican beer later this week). While a little pricey for a dive of sorts, the food at this place was a pleasant surprise.

For breakfast, hit up Yurta — fresh squeezed OJ, eggs, bacon, toast, and incredible homefries for $3.95. Nuff said.

All in all, Old San Juan is a great place to hit up if you are looking to explore Puerto Rico outside of a resort. If you are looking casinos and Senior Frogs, you’ll be able to find that. But if you are looking for cobblestone streets, pastel buildings, awesome food and just enough seediness to keep things interesting Old San Juan is worth checking out. Oh yea, and the coffee (always made with steamed milk) is awesome… drink it wherever you go.

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