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A Taste of Old San Juan: Eating My Way Through Puerto Rico’s Capital

Old San Juan, Puerto Rico from San Cristobal Fort

San Juan, Puerto Rico is a food lover’s paradise. The old city center is home to everything from traditional Puerto Rican fare to an authentic German brewpub, all packed into one square mile of colorful, cobbled lanes. It has been compared to the French Quarter in New Orleans for both its authentic architecture and its phenomenal cuisine, and I can see why. And like New Orleans, while it is technically a part of the U.S., all of these distinctions make it feel more like a world away.

So, when my 30th birthday rolled around, I thought what better way to celebrate than by eating my way through a historically preserved city known for it’s delicious food and gorgeous weather. For once, I didn’t even need to pack my passport! A few weeks after booking a long weekend for my husband and myself, we are wheels up on an early morning flight headed to check out the city’s famous cuisine… and the architecture, too.

After checking into our hotel and briefly freshening up, we’re on our way to our first stop: lunch. I’m a planner. Usually when we go on a trip I have a detailed itinerary laid out of everything we’re going to cover and when, a list of must-see sights, and at least an idea of where we might want to eat. However, it’s my birthday; so, for once I’ve decided to wing it. We wander the colorful streets marveling at the perfectly preserved colonial-era buildings, listening to the rumble of our stomachs as we search for the right spot. And after a little while, we come across exactly what we are looking for: a little restaurant, with a traditional menu, packed with locals. It doesn’t look like much compared to some of the bigger, more loudly decorated places on the main drag trying to tempt tourists inside with specials and more extensive menus, but if there’s one thing I’ve learned during my travels, it’s that for the best food, you follow the locals not the gimmicks.

We head inside Fefo’s Deli & Tapas (on Calle Tanca & Calle San Francisco) and take a seat at one of the self-seating tables. It’s sort of a mix between a sandwich place and a sit-down restaurant. There is a deli case at the diner-like counter, and a kitchen window behind it churning out Puerto Rican and Italian cuisine: nothing fancy, just tasty dishes that the patrons around us all seem to be enjoying. Our waitress brings us a menu, but after glancing it over for a few minutes, I decide to go with my typical stand-by order.

“What do you recommend?” I ask her.

“What are you in the mood for?” she asks. “Italian, traditional, a sandwich?” She recommends several of their Italian dishes, which sound good–I’ve seen a few come out of the kitchen and they look delicious–but that isn’t why we’re here.

“Something traditional,” I reply.

She turns my menu to the back and points to the top. “We have mofongo and trifongo. The trifongo is my favorite.”

“What is that?” my husband asks.

I know what mofongo is; it’s about as traditional a dish as you can have in Puerto Rico. My friends who grew up here have already made me promise I will try it at least once while I am in the city, but I have never heard of trifongo.

“Mofongo is a traditional dish made with mashed green plantains, garlic and olive oil; trifongo is a similar dish but with mashed yucca, sweet plantain, and green plantain all together. You can get it with chicken or beef or shrimp,” she answers pointing out the options on the menu.

We both agree to try the trifongo, mostly out of curiosity. Neither of us has ever tasted yucca or green plantain, but we love sweet plantains, and this sounds like an interesting variation on the more traditional mofongo. Then we are asked to choose between a garlic butter sauce or a red creole sauce for our dishes. We both opt for the red sauce, and our orders are placed.

In no time at all, we each have a huge dish of steaming food in front of us. The trifongo, shaped like a half-sphere, sits flat side down on one side of my plate, while the chicken I ordered is on the other, cut up and sautéed with onions and green peppers. The entire dish has a light red sauce over top of it. I half expected the trifongo to be stuffed with the chicken or overtop of it, but as I will learn over the next few days, there are countless varieties of mofongo served throughout the island, and just as many ways to serve it.

Trifongo with Chicken and Creole Sauce

As I dig into my dish, I anticipate the sauce will be spicy. Usually anything creole has a little bit of a kick to it, but it turns out its relatively mild. Puerto Rican cuisine is not known for being hot. It is more similar to Cuban food than Mexican. The trifongo is an interesting combination of flavors and textures. The yucca tastes similar to a potato–very starchy; the sweet plantain tastes as its name suggests and has a soft texture, while the green plantain adds a bit of crunch to the combination. I have heard that you either love or hate mofongo, and maybe that is true, but my husband and I agree that as for trifongo, we don’t love it or hate it. It’s definitely different! The sauce blanketing the dish is delicious, and the chicken is extremely tender. The combination of the three together is tasty, and we enjoy our lunch, but it is not quite what I was expecting. We decide for our next meal we’ll try mofongo to compare the two.

We wander the Old City for the rest of the afternoon and then take a nap before dinner. Puerto Ricans eat dinner late, and we were up before dawn to catch our flight. After our siesta, we head out for dinner and drinks. This time we get a dinner recommendation from a local for the ‘best mofongo around.’ Of course everyone has an opinion on this, but we take his recommendation and head off to Raices (on Calle San Sebastian and Calle del Cristo). We don’t have a reservation, and it’s a Friday night, so there’s a pretty long wait, but there are seats available at the bar. I don’t mind sitting there–maybe I’ll even get a chance to brush up on some of my Spanish with the bartender–so we are quickly escorted to two empty seats.

I order a mango mojito and my husband orders a Puerto Rican beer, which we both end up liking a lot. We look over the menu, but we already know what we want. We each order the shrimp mofongo with a garlic butter sauce–what we were told we ‘had to try it’ by the local who recommended it.

While waiting for our meals, we fall into conversation with the man sitting next to us–yet another reason why I like the bar, you get to meet the locals. He was born in Puerto Rico, but moved with his family to Chicago as a child, he tells us. He now owns a vacation home in San Juan and tries to get back as often as work will allow.

When his appetizer comes, I comment that it smells delicious and ask what it is. He tells me, but I can’t quite translate it with my rudimentary grasp of the Spanish language. I ask him again, but still not quite knowing what the translation is, I give up. I’ll just call it ‘delicious smelling chunks of meat.’

“Would you like to try it?” he asks offering us both his plate. We agree to try it–just for research purposes, of course. Probably much like hotdogs, I don’t want to know exactly what is in it, but it’s very tasty, and we complement his menu selection.

“Every time I visit, I have to come here at least once for the pork chops,” he says.

“They’re that good?” I ask.

“They’re that good,” he confirms, and when they come out, practically hanging off of the plate due to their enormous size, sizzling appetizingly, I can see what he means.

We contentedly sip our cocktails, occasionally making small talk with the bartender and our newfound friend until our food arrives. Then our attention is diverted to the delicious smelling meals in front of us.

The mofongo is served in the most traditional way possible, in a pilòn. A pilòn is more or less a large wooden mortar and pestle. The only way to prepare authentic mofongo is with a pilòn, smashing up the plantains, without pureeing them. You will not find anyone in Puerto Rico preparing mofongo in a food processor. It must be made by hand, smashed to the correct consistency, and then baked.

Mofongo with Shrimp and a Garlic Butter Sauce & Puerto Rican Beer

Our mofongo takes the shape of the bowl it sits in, and the center is stuffed full of what must be at least 8 large-sized shrimp. Then, the entire dish has a garlic butter sauce that has worked its way through the plantains all the way to the bottom of the wooden bowl. The smell is heavenly, and the taste is just as good as the smell. I may have been a bit ambivalent to trifongo, but I am definitely on the love side of the debate when it comes to mofongo. It is next to impossible for me to finish my entire dish. We could almost have shared the generous portion. As I get closer to the bottom of the dish, there is more and more sauce. This makes the it both increasingly tasty (everything is better with butter) and increasingly rich. About 3/4 of the way through, I have to call it quits–not because I want to–every bite is tastier than the last–but because I’m already well past the point of full. Plus, I’ve been warned by our friend at the bar that I have to leave room for dessert.

His dessert suggestion is not something that I would ever pick off of a menu, but at this point I trust his judgment when it comes to food, so I let him order it for us. He orders the Casquitos de Guayaba con Queso Blanco (guava fruit in syrup with white cheese made with cow’s milk) and insists that we’ll love it. I have never eaten guava fruit. I’ve had things flavored with it, but I don’t know what the actual fruit even looks like. So, I’m excited to try yet another new food today.

When our dessert comes out, I am pleasantly surprised. The best way I can describe it is that it resembles a deconstructed cheesecake. The cheese is extremely mild, and on its own I would probably not have much of an opinion on it either way. In conjunction with the guava fruit–which is poached in a simple syrup–and a white chocolate sauce that is also on the plate, though, it is transformed into something absolutely delicious. The mild crumbliness of the cheese with the sweetness of the sauce and the fruit is perfect. It is just light enough after our heavy dinner.

Casquitos de Guayaba con Queso Blanca

This would most definitely be a perfect cap to our evening, but in talking with our new friend, he mentions piña coladas–my all-time favorite drink. I know the drink was invented in Puerto Rico but by who is up for debate. Two place: Barrachina in Old San Juan and the Caribe Hilton in Condado (just outside of Old San Juan) both claim to have invented it. My guidebook actually refers to it as ‘The Piña Colada Wars.’ He mentions that Barrachina is nearby, about a 4-block walk. That’s enough to divert me from my early-to-bed plan to an evening stroll and piña colada-before-bed plan. He provides us with directions and wishes us a good rest of our trip. We pay our tab, say our goodbyes, and head off to our next stop.

Barrachina is part restaurant, part bar, and part outdoor courtyard. Walking into the bar, you feel more like you’re on a Latin-American patio than in a restaurant. There are several tables, but the general feel is very open and airy. We take seats at the bar and order up two piña coladas.

“With rum or without?” the bartender asks.

The answer is of course “with,” and soon we each have a drink set down before us. There is no whipped cream–more typical in the continental U.S.–just a cherry on the top.

At Birthplace of the Piña Colada

The creamy, coconutty, pineapple concoction is absolutely delicious (which can be supported by the fact that we most definitely drink more than one each). It is different from what you would typically get in a stateside bar. It tastes fresher, and is a little more liquid-like than the frozen drinks at home. I don’t know what their rival’s tastes like, but these are definitely the best piña coladas I’ve ever had.

When we’ve had our fill of piña coladas and paid our bar tab, it’s time to head back to the hotel for a good night’s sleep. It’s been a rewarding, calorie-filled day. I’m sure tomorrow will be waiting with another adventure and plenty more new foods to try!

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