Here’s the story of our unexpected but absolutely wonderful trip to San Juan, Puerto Rico.
There are many ways to plan a vacation to Puerto Rico. The way my family did it was to plan months and months in advance… to go to Texas.
And to then scrap the entire Texas trip just hours before we were supposed to leave, and embark on a trip to Old San Juan, Puerto Rico instead!
I must say though that we would not have thrown ourselves into such chaos voluntarily. Events out of our control forced this quick-change upon us, namely our airline cancelling our flight just a few hours before we were supposed to be at the airport. Now sit right down and you’ll hear a tale…
This trip was a gift from my mom, in the form of her accumulated airline miles. It was hard for our family (my husband, our college-age daughter, high school-age son, and me), to narrow down where in the U.S. we should go: top choices included San Francisco, New Orleans, Austin, and Seattle. In the end we chose a beach vacation: South Padre Island in Texas, at the very tip of the barrier island that runs along the coast of the state.
For months we eagerly anticipated this beachy trip, which would begin right after school got out for the summer.
I was looking forward to checking out the food scene, and hopefully getting a taste of authentic Mexican fare! We also spent months explaining to friends and family where and what South Padre is: not many people in our neck of the woods had heard of it.
The evening before our flight was scheduled to leave, we were at my father and stepmother’s house wrapping up a lovely dinner and get-together. That all came to a halt when my husband and I received text message alerts from the airline: the first leg of our flight was cancelled. We had to end our visit rather abruptly, and we made a beeline to my mother’s house to figure out what to do – she is infinitely more air travel savvy than we are.
The set-up in her work-from-home office is an impressive one: three monitors spread across two desks. She was at the computer, headset on, jumping from screen to screen with a quick swivel of her chair. It was like watching member of NASA Mission Control. Though she expertly wrangled with the airline representative to try to salvage our Texas vacation, between cancelled flights, sold out flights, and our window of available travel time, we could not put back together the pieces of our broken trip.
There was a mourning period, with near-tears kids and silence in the house. The airline rep was still on the phone, mumbling and apologetic – my mom was having none of it. I sat wondering if there was something I could quickly bake that would everything better. After a bit of all this, my husband was the first to rally, and he began to search: what other flights were leaving the next morning? We saw and briefly considered Charleston, South Carolina, but it looked to be a rainy week in the forecast there, and no one was interested in vacationing in the rain.
Then he saw it, like a lighthouse beam in the fog: a cheap flight to Puerto Rico. We had never been to Puerto Rico! We did a quick assessment: would this destination fit in our vacation window? Yes! Were there any hotel rooms available? Yes! Does our youngest need a passport to get there? No! Can we afford a week of eating and entertainment in Puerto Rico? ….no clue! Well then: Puerto Rico it is! Even the airline rep, who we still had on the phone, was excited for us! By the time we pulled the trigger, cancelled 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 it was time to pile into the car and head to the airport.
That day as we moved through the airports in Albany and then Baltimore, we were giddy. We were exhausted too, but fueled on 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 Phoenix.
It gave us all an Amazing Race feeling: last-minute flights, racing to the airport on no sleep, not knowing what the destination would be like. 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 and felt the tropical heat, saw blue skies and palm trees, we felt like we had reached heaven.
In the week that followed we were not disappointed, not even once. It was by chance that we found a hotel in our price range that happened to be located right in Old San Juan. It was perfectly situated on Calle Marina at the port, and allowed us to walk everywhere: to cafés, restaurants, shops, and plazas.
I could write on and on about all that we saw and visited there: our tour of 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, Uber trips to the beach.
We found blue cobblestone streets, and enjoyed a birds-eye view of the port from the hotel’s roof-top pool.
The most unexpected stop was at Save-A-Gato: a cat sanctuary! It was located along the road leading to the San Felipe del Morro Fortress, a little outdoor haven for cats with staff caring for and feeding them.
We spent good long while resting there, petting and naming the dozens of cats that wander and lay around the road!
(Note: if you are not a REALLY huge fan of cats, you may not enjoy this spot as much as we did!)
Tempting as it is to get into it all, I’ll stick to the delectable points of our trip!
We did not give ourselves a mandate about eating out on this trip: like, to visit as many eateries as we could, or to try a different place for every meal each day. We just let our feet take us wherever they wanted.
That first afternoon, our feet and noses took us to one of several food trucks parked along Dársenas Square. Our first meal in San Juan was at El Trompo food truck, and we had deliciously seasoned, large, soft burritos with tender chicken, lots of cheese and veggies, and big chunks of pineapple.
They were cooked up simply and quickly, and were really satisfying. We enjoyed them sitting out in the pigeon-filled plaza with cold beverages from a nearby outdoor bar: the local Medalla beer for me and my husband, and water for the kids.
My husband and I think Medalla may be the Coors Light of Puerto Rico, but on those hot, humid days it was always refreshing, and went with every spicy dish we tried!
After a few hours of walking, exploring shops and sights up and down the cobblestone streets, we found a little hole-in-the-wall place to stop for a snack: La Güerita. (We are always on the lookout little spots to try, after our adventures last summer checking out 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.
The staff inside was friendly, music from Los Tigrillos and the like filled the air. The bottles of Medalla beer were icy cold, and the menu had an intriguing assortment of “antojitos” (little bites, like tapas) and small tacos with various fillings.
Spoiler alert: we ate at La Güerita, this unassuming spot, six times in four days!
The tacos consisted of little corn tortillas that were grilled and soft, and there were several fillings to choose from. These included ground chorizo, with or without potatoes. There was Tinga which was chicken cooked with Mexican chiles and spices.
The Pastor filling, marinated pork cooked on a vertical spit with a whole pineapple at the top of the spit, was seared in an open flame before being sliced off the spit along with a few shaves of pineapple. Pollo en Escabeche was also very good: chicken marinated in garlic, onion, vinegar and spices.
My son preferred the humbly named Beefsteak, which does not nearly do justice to the flavor of the tender, juicy, perfectly seasoned strips of beef that came in that taco. The tacos came to our table served on wooden planks, and with three amazing sauces that we quickly consumed: cilantro crema, chipotle piña, and habanero. The cilantro crema was my son’s favorite: 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.
Haley noticed that the chipotle piña, with smoky heat from the chipotle peppers and sweetness from the pineapple, was perfect on the Pastor tacos.
Our approach, every time we ate at La Güerita was to order one round of the smallest tacos plus chips and salsa. And then after quickly eating all that, we would order a second round of tacos.
And on at least two of the six visits, we went for a third round of tacos! We could not resist these savory little bites, and icy Medalla beer was perfect to wash them down.
My daughter fell for the margaritas there: tall glasses of a classic sweet and sour margarita, with a spicy blend of salt, achiote, and chile on the rim. (This was her first experience being able to enjoy a drink 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 juices there that were new to all of us: Jamaica flower and tamarind.
We had the same table at every visit, a pack of souvenir playing cards (purchased at a nearby shop) for games of Pitch, and lots of enthusiastic greetings from the owners and staff as they saw us return day after day.
On our second day eating there, one of the owners bought us a round of Tequila Sunrise shots (thoughtfully including a virgin Sunrise for our son), and on a subsequent visit a special dessert was prepared ahead for us: cream cheese and cajeta empanadas with ice cream, drizzled with caramel and sprinkled with cinnamon.
(Cajeta is like caramelized, sweetened condensed milk, but made with goat’s milk instead of cow.) We were so happy coming back again and again to this little taqueria.
Another restaurant we made our own was La Mallorquina, first opened in 1848. We made this our daily breakfast spot.
La Mallorquina is stunning inside with on Old World feel from vaulted ceilings, tall walls in shades of pale yellow and gold, dark wood tables, chairs and bar, a floor of black and white tiles, and massive antique mirrors in imposing and ancient-looking frames. We really enjoyed the open-air atmosphere created by three sets of huge French doors open to the street.
Beyond the dining area was a little courtyard-styled 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 café negra, 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 delicious alongside everything else.
It was also interesting as part of a grilled ham and cheese sandwich. (It was on the menu, so I had to give it a try!) It was the first grilled cheese I’ve had with a crunchy-sweet crust on the surface of the bread, thanks to confectioner’s sugar sprinkled on before grilling.
One of our lunch stops came after our first beach trip.
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, and we sat at tables set out on the sidewalk.
We just had to take in the beautiful weather everywhere we went.
On the advice of a friend through Facebook, we went out late one evening to El Jibarito. We had there an array of appetizers to try: alcapurrias, which were plantain fritters with a beef filling, bolitas de queso – literally, fried balls of cheese, sorullos de maiz, which were corn fritter sticks, and patelillos de carne, little beef turnovers.
They were all delightfully greasy and salty: in other words, a perfect late night snack. I enjoyed the alcapurrias the most. Plantain is a new ingredient for me, but is very common in Puerto Rico. We finished the meal with a slice of cold, caramel flan that was smooth and rich.
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, and the rest of us tried fruity sangria (for me), a mojito with sharply refreshing mint (for our daughter), and more cold Medalla for my husband. (Who asked the bartender to open the bottle for him, assuming the caps were not twist-offs, and who felt really silly when the bartender did open it for him – by twisting it off.)
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 beach side bar at a hotel on Condado Beach. (We realized after the fact that the bar was only intended for hotel guests. We realized this when the bartender asked us which room number to charge our drinks too! It was tempting to pick a number, any number… but we were good and paid him in cash.)
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. But, the authentic dishes at that restaurant turned out to be seafood-based, and for the most part we don’t care for fish. The restaurant with the dancing, and many other sit-down places were tempting, but we were just too hooked on the casual, neighborhood feel of our two spots: one for breakfast and one for most of the rest of our food!
As with most vacations, our time in Old San Juan flew by way too fast. 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 friendly, proud of their food, and happy to see us.
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 with us a couple of Medalla bottles full of sand from Condado Beach, 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? The buildings in shades of fuchsia, aquamarine, periwinkle, mint…. they are dazzling.)
As we traveled home we also found ourselves humming and singing ‘Despacito’. And we actually didn’t hear that particular song so much in Old San Juan, but I suppose we had it in our heads because we heard lots of other music in Spanish. And because one of the lyrics in ‘Despacito’ is, “This is how we do it down in Puerto Rico.”
Tacos, Medalla, Pitch, chorizo, Mallorcas, Pastor, gatos… that’s how WE did it down in Puerto Rico!