Old San Juan, Puerto Rico | Delectable Destinations

Here's the story of our unexpected but absolutely wonderful vacation in Old San Juan, Puerto Rico, and all the delicious eats we found there.

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There are many ways to plan a vacation to Puerto Rico. The way my family did it in a rather unconventional way, by first planning to go to Texas. And then by scrapping the entire Texas trip just hours before take-off and embarking on a trip to Old San Juan, Puerto Rico instead.

We would not have thrown ourselves into such chaos voluntarily, but events beyond our control forced this quick change. Now sit right down and you'll hear a tale...

Doomed plans for Texas

It wasn't easy for my husband, college-age daughter, high school-age son and me to narrow down where in the U.S. we should go for vacation: top choices included San Francisco, New Orleans, Austin, and Seattle. In the end, we went with a beach destination: South Padre Island in Texas, located at the very tip of the barrier island that runs along the coast of the state.

I was excited to check out the food there and hopefully get a taste of authentic Mexican fare! We also spent months explaining to friends and family where and what South Padre is, as not many people in our neck of the woods had heard of it.

The flight and hotel plans were set up way in advance, but it wasn't until the evening right before our morning flight that it all came to a screeching halt—in the form of a text message alert from the airline, notifying us that the first leg of our flight was canceled due to the threat of hurricanes.

We were staying with my mom that night. Since she had gifted us the airline and hotel rooms for our vacation, when news of the cancellation came she immediately went to work. Her frequent travel for work has honed her skill at wrangling with travel industry customer service reps. We watched and listened as she moved between three screens across two desks in her home office, headset on, fingers flying over the keyboard. But between the many canceled and sold-out flights, we saw that it would be impossible to save our vacation.

We were in shock with near-tears kids and silence in the house. I sat wondering if there was something I could quickly bake that would make everything better. Fortunately, my husband was the first to rally and he began to research: is there anywhere we can go?

Then suddenly—Puerto Rico

That's when my husband saw it, like a lighthouse beam cutting through the fog: a cheap flight to Puerto Rico. We had never been to Puerto Rico! We quickly assessed: would this fit in our vacation window? Yes! Are hotel rooms available? Yes! Are any passports needed? No!

Could we afford a week of eating and entertainment in Puerto Rico? No clue!

Well then, Puerto Rico it is! Even the airline rep, who had been on the phone with my mom for ages was excited for us! By the time we canceled all our reservations in Texas and made new reservations in Old San Juan, it was 1:00 AM. We all grabbed two hours of restless sleep before piling into the car and driving to the airport.

That day as we moved through the airports in Albany and then Baltimore, we were all giddy. Exhausted too, but fueled by an exhilaration that one can only experience after seeing a long-awaited vacation crash, burn, and then be reborn from the ashes like a mythical phoenix.

The last-minute flights, racing to the airport on no sleep, not knowing what the destination would be like, all these elements gave us Amazing Race vibes. We shared teasing tidbits on Facebook with friends and family as we made our way south, so they could experience the lows, highs, and eager anticipation with us.

When we finally emerged from the airport in Old San Juan, felt the tropical heat, saw blue skies and palm trees, we felt like we had reached heaven.

Beautiful Old San Juan

In the week that followed we were not disappointed, not even once. It was by chance that the hotel we found in our price range just happened to be located right in Old San Juan. It was perfectly situated on Calle Marina by the port, a location that allowed us to walk to cafés, restaurants, shops, and plazas.

Some of the spots we saw and visited there included the historic fort Castillo de San Cristobal, the massive, centuries-old gate of Puerta de San Juan, the beautiful Catedral de San Juan Bautista that sits at the top of the street from the gate, and of course the beaches.

Beautiful blue cobblestones pave all streets in Old San Juan, and the buildings along these narrow roads are painted in stunning, shades of aqua, yellow, pink, and green. And we were thrilled with our birds-eye view of the port from the hotel's roof-top pool.

We found a cat sanctuary

The most unexpected spot we found to visit there was the Save-A-Gato cat sanctuary! Located along the road leading to the San Felipe del Morro Fortress, it's a little outdoor haven for the city's population of feral cats, with staff who care for and feed them.

We spent a good long while resting there, petting and naming the dozens of cats that wandered the grounds and lay stretched out on benches in that adorable, languid way that cats do.

(Note: if you are not a REALLY huge fan of cats, you may not enjoy this spot as much as we did!)

The start of our Medalla Light obsession

We didn't bother with any kind of mandate about eating out on this trip—like to visit as many eateries as possible, or to try a different place for every meal every day. We just let our feet and tastebuds take us wherever they wanted.

That first afternoon we found several food trucks parked along Dársenas Square. Our first meal in San Juan was at El Trompo food truck, and we had deliciously-seasoned, soft burritos full of tender chicken, lots of cheese and veggies, and big chunks of pineapple.

The burritos, cooked up simply and quickly, were really satisfying. We enjoyed them sitting out in a pigeon-filled plaza with cold beverages from a nearby outdoor bar, and that's when my husband and I first tried the local Medalla Light beer.

We think this may be the Coors Light of Puerto Rico, a super light lager that goes down as easily as water. On that hot and humid day, it was so refreshing, and perfect to wash down our spicy food.

Tacos and more tacos, at La Güerita

After a few hours of walking, exploring shops and sights up and down the cobblestone streets, we found a hole-in-the-wall place to stop for a snack: La Güerita. (We are always on the lookout for little spots to try, after our adventures one summer finding hole-in-the-wall spots throughout Vermont.)

A small doorway opened to a long space inside, with a bar along the left wall and wood tables and benches arranged along the right.

What we found that day was an extremely friendly staff, music from Los Tigrillos and the like filling the air, and icy-cold bottles of Medalla. The menu had an intriguing assortment of "antojitos" (little bites, like tapas) and small tacos with several different fillings.

Spoiler alert: we liked it so much that we ate at La Güerita, this unassuming spot, six times in four days!

The tacos consisted of soft, grilled corn tortillas and there were several fillings to choose from, like ground chorizo with or without potatoes, and tinga—chicken cooked with Mexican chiles and spices.

The pastor filling, marinated pork cooked on a vertical spit with a whole pineapple at the top, was seared in an open flame before being sliced and served with a few shaves of pineapple. Pollo en Escabeche was also very good: chicken marinated in garlic, onion, vinegar, and spices.

My son's favorite taco was the humbly-named "beefsteak", which does not nearly do justice to the flavor of the tender, juicy, perfectly-seasoned strips of beef inside. The tacos came to our table on wooden planks with three amazing sauces that we quickly consumed: cilantro crema, chipotle piña, and habanero.

The cilantro crema, my son's favorite, was a simple, creamy dip loaded with fresh cilantro. I gravitated towards the habanero which was thick with a sweet base (honey, I think) and packed quite a punch.

My daughter noticed that the chipotle piña, with smoky heat from chipotle peppers and pineapple sweetness, was perfect on the pastor tacos.

Each time we ate at La Güerita we ordered one round of tacos plus chips and salsa. And then after quickly eating all that, we would order a second round. On at least two of the six visits, we went for a third round of tacos! We just couldn't resist these savory little bites with icy beer to wash them down.

My daughter fell hard for their margaritas, tall glasses of a classic sweet and sour blend with a rim coated in spicy Tajín. (This was her first time enjoying a cocktail with us, thanks to a lower drinking age in Puerto Rico.) My son was adventurous too, trying new-to-him taco fillings as well as juice drinks like Jamaica flower and tamarind that were new to all of us.

We had our own regular table where we played a few games of Pitch every visit time. We became such regulars that week that on one visit the owners bought us a round of Tequila Sunrise shots (including a virgin Sunrise for our son.)

On another visit, they gave us a special dessert of cream cheese and cajeta-filled empanadas with ice cream, caramel drizzles, and cinnamon. Cajeta is like a goat's milk version of caramelized, sweetened condensed milk. 

We were so happy coming back again and again to this little taqueria.

La Mallorquina for breakfast

Another spot we made our own was La Mallorquina, a restaurant that first opened in Old San Juan in 1848. We made this our daily breakfast destination.

La Mallorquina is stunning inside with an Old World feel from vaulted ceilings, the bar and tables of dark wood, and a floor made of black and white tiles.

Tall walls in shades of pale yellow and gold held massive, antique mirrors in ancient-looking frames. We really enjoyed the open-air atmosphere created by three sets of huge French doors that open to the street.

Beyond the dining area is a little courtyard-style space with sunlight from above and a pale yellow fountain with scalloped sides placed in the center. It is an elegant space, but with the cool breeze from outside and relative quiet of the mornings, it felt very casual and comfortable.

We enjoyed breakfasts of espresso, hot tea, ham croquettes, sausages, and eggs. My daughter and I were obsessed with the Mallorcas bread, a pillowy-soft sweet bread baked locally and delivered to the restaurant daily. It was interesting as part of a grilled ham and cheese sandwich. It was the first time I had a grilled cheese with a sweet, confectioner's sugar crust on the bread. Absolutely delicious!

A rum bar

On the walking day that took us to the cat sanctuary and the Catedral, my husband spotted a hole-in-the-wall rum bar, Casa Melaza, where we could find some refreshment and shade from the heat of the early afternoon.

The space inside was smaller than our living room (which is pretty small.) There, we gave our boy plenty of cold water while I tried their fruity sangria and our daughter enjoyed a mojito with the sharp, refreshing bite of mint.

It was more cold Medalla for my husband who, assuming the caps were not twist-off because we had always received bottles already opened, asked the bartender to open the bottle for him. And he felt really silly when the bartender did open it for him—with a simple twist. And my husband sheepishly sipped as we, and the bartender, laughed.

More food stops in Old San Juan

One of our lunch stops came after our first beach trip at Ocean Park: La Patisserie French bakery and bistro. There we had an interesting mix of food: for my husband, daughter, and I, tacos filled with Creole-spiced chicken with French fries on the side. My son had a grilled ham and cheese (no sweet bread on this one!) It was a savory and satisfying lunch at tables set out on the sidewalk.

On the advice of a friend, we went out late one evening to El Jibarito. There was an array of appetizers to try there, like alcapurrias which are plantain fritters with a beef filling, bolitas de queso—literally fried balls of cheese, sorullos de maiz which are corn fritter sticks, and patelillos de carne, little beef turnovers.

All the treats were delightfully greasy and salty, a perfect late-night snack. I enjoyed the alcapurrias the most. We finished the meal with a slice of cold, caramel flan that was super smooth and rich.

Other edible finds were drinks served in hollowed-out pineapples, served from a little table just a block away from the "secret staircase" that led us from our hotel up to the cobblestone streets each morning. We didn't get to try one of those drinks, because they were a little pricey. Our daughter wanted to take a selfie with one, but she settled for a hollowed-out coconut (just a display one) that we "borrowed" from a café table.

There were simple treats too, like packets of dried mangoes and apricots that we took to the beach, and thin, wafer cookies will coconut and lemon fillings. My son also tried a fruity, kid-friendly, blended frozen fruit drink from a beachside bar at a hotel on Condado Beach. We realized too late that the bar was only intended for hotel guests—when the bartender asked us for our room number! It was tempting to make one up, but we were good and just paid him.

All of these stops were, of course, made when we were not at La Güerita or La Mallorquina. We debated finding other places to eat, giving consideration to a restaurant with live, Flamenco dancing, as well as a restaurant recommended by one of our Uber drivers for its authentic Puerto Rican food. (Mostly seafood and most of us don't care for fish.)

However, we were just too hooked on the casual, neighborhood feel of our two favorite eateries, one for breakfast and one for everything else. It seemed perfect to our family to cling to these spots that made us so happy, where the food was authentic, freshly-made, and flavorful. Where we could relax and play a few hands of cards, and where the staff was proud of their food and happy to see us.

A vacation to remember!

As with most vacations, our time in Old San Juan flew by way too fast. When we left Puerto Rico we were sunned, serene, full of tacos, speaking a little more Spanish than we could before, and feeling like fate gave us an incredible experience that we could not have anticipated.

We took a couple of Medalla bottles full of sand from Condado Beach with us, a wooden machete with "Puerto Rico" seared into the blade, some touristy t-shirts and hats, and a print by a local artist for my mom, depicting the vividly painted buildings on Calle Sol.

Did I mention the color in Old San Juan? Not only the buildings but the brilliant blue of the ocean, the vibrant food, and the trees and flowers everywhere.

As we traveled home we also found ourselves humming and singing 'Despacito'. We didn't hear that particular song so much in Old San Juan (much more once back home,) but I suppose we had it in our heads because we heard so many rhythmic, Puerto Rican tunes everywhere we went.

One of the lyrics in 'Despacito' is, "This is how we do it down in Puerto Rico." Well, tacos, Medalla Light, Pitch, chorizo, Mallorcas, pastor, margaritas, los gatos... that's how WE did it down in Puerto Rico!

This post is dedicated to my amazing family. I love all of my adventures with you! ♥