Old San Juan, Puerto Rico

I’ve spent many winter vacations in Puerto Rico (see last post), but I havn’t really explored San Juan, particularly the historic district of Old San Juan at all.  In the past few years, Mister and I have tackled one adventure per vacations [kayaking in the bioluminesent bay, rappelling down waterfalls, etc.], so I wanted to take the opportunity for some exploring.

Via Air BnB, I booked a two night stay at Portal del Sol.  This was my first experience with Air BnB, but after seeing the amazing architecture of Old San Juan I knew I really wanted to be able to live in it, even if just for a nanosecond.  This apartment was perfect, and our host Juan was great at making us feel welcome, even going so far as to giving us dinner advice via text when we were overwhelmed with options.

We were warned that parking can be tricky in Old San Juan; the combination of narrow streets, cobblestone, and limited parking was a recipe for some frustration for sure.  We found the apartment, then circled the block a dozen times looking for any available parking.  At peak crankiness, we saw a car just leaving and decided to nab the spot and then find our way back to the apartment on Calle de Sol; as luck would have it, we plugged the address into our phone GPS only to find we had literally parked right outside of the rental!

We explored the city, the sights, the food, the forts.

This city is so incredibly vibrant and alive, while being overwhelmingly historic all at the same time.  Being the history nerd that I am (BA American History, MA Public History), I was running around the forts like a kid in a candy store. The forts are National Parks, and one admission pass is good for both for a few days.

In addition to the two forts, definitely take the time to stop by La Casa Blanca, which was only a few blocks away from our apartment (and the forts, everything is within relative walking distance).

It was originally built as a home and protecting fort in 1521 for Juan Ponce de Leon, though he died prior to inhabiting the home.  For the next 250 years, Casa Blanca was home to the descendants of Ponce de Leon, up until Puerto Rico became a United States territory, at which time the house became home to the locally stationed US Army commander.  We arrived about a minute before they opened, and Mister asked if we could receive a tour; I’m thankful he did because the government employed staff member was so incredibly enthusiastic about the home that it was contagious.

I was so excited about seeing every square inch of cobblestone and Spanish architecture, that every morning I woke up just a bit before Mister to explore the city on foot, filling my backpack with breakfast treats and my hands with coffee along the way.

Recommendations for grab and go breakfast:

1.)Cafeteria Mallorca had a window full of freshly baked goodies, with an old school diner vibe inside.  The place was packed with locals and touring families alike enjoying sit down meals, but I focused on the cheese and fruit filled danishes that were too tempting to pass up.  Their specialty is the mallorca their named after, which is a  ham and cheese (sometimes egg) sandwich on a buttery, sweet bread.  I wanted to enjoy the sweet bread on its own, but maybe next year I’ll be able to pass up the sweets in favor of the sandwich.

2.) Bad Ass Coffee, now I know that Puerto Rico is known for some really amazing coffee so stick with me on this one.  If you havn’t had it, Puerto Ricaan coffee is more like espresso on the range of intensity and servings; sometimes when its hot and humid you want something colder and sweeter.  This place is a franchise based out of Hawaii, and while I downed some local coffee in the afternoons and evenings, I was all about their blended chais and almond milk lattes at Bad Ass Coffee in the morning.


(proof that I had local coffee, and that I apparently have a weird lobster hand)

3.) SuperMax, yup a supermarket.  The Old San Juan location had a great selection of fresh fruits and veggies, plus bottled drinks and booze to keep our temporary home stocked with some options.  The other location of SuperMax, outside of Old San Juan was closer to the major hotels, open 24 hours, and had a giant parking lot.  In addition to these minor luxuries, it has a little coffee shop, a giant wine selection, full service deli, hot food, store made sushi, and even an in-store, make your own acai bowl/smoothie option.  Live like a local, right?

For dinner in Old San Juan, the restaurant options can be overwhelming and a bit daunting.  Some are clearly tourist traps, some are hard to identify as tourist traps, and some are really amazing food.  How do you tell the difference?

On our first night, we consulted Yelp as much as we could, but we were still sort of confused, hungry, and tired.  As I mentioned earlier, we turned to our Air BnB host, Juan, via text and he was gracious enough to recommend El Jibarito, which was just a block or so away from our apartment.  If the pictures above don’t speak for themselves, let me just tell you that this was the perfect blend of vacation indulgence (i.e. sweet, blended rum drinks) and fresh local flavor.  It was a great way to start our mini vacation within our vacation.


Our second dinner was at Verde Mesa.  This was an experience unlike anything else we had on the island, and that I’ve probably had in a while.  This restaurant had a whimsical environment, with a menu focusing on pescetarian and vegetarian options exclusively.  The service, though sometimes slow, was impeccable.  The bill was high, but the experience was definitely worth it; scallops so buttery in texture that they literally melted in your mouth, or a black olive couscous that was so flavorful it could have stood on its own as a dish.


Seriously, just looking at those perfectly boiled eggs makes me want to eat that dish a million times over.




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