Eating up in Old Town San Juan

Despite everything Puerto Rico has endured, from devastating hurricanes, droughts, floods and a generous helping of corrupt politicians, the pervasive cheerful charm and gracious hospitality never seems to wane. For the perfect mid-winter respite from the sub-zero northeast, Puertorricueños know exactly how to pamper their (quasi) countryfolk with just the right mix of ethnic culture, creature comforts and a very hip dining scene. But beyond the Lego landscape of indistinguishable glass and concrete towers elbowing for a view of the coastline, it is the 1-square mile of Old town San Juan, (now a UNESCO World Heritage site) that truly embodies the city’s astonishing history and unique traditions – while offering a sumptuous feast for the senses. And I mean all of them.

Ham & Cheese Mallorca Roll

I’ve found that the best place to savor your way into a foreign culture is from street level. You not only get the benefit of a unique perspective of the historic character and architectural influences surrounding you as you hear, smell and taste the nitty-gritty of a city, but walking between bites is supposed to be very good for the digestion too! Nahiomy, our delightfully approachable fountain of information tour-guide punctuates our casual sojourn along the cobble-stoned streets with history lessons about San Juan’s storied past, (including the clerical mishap where the Spanish royal court accidentally transposed the original name of the island, San Juan-after St. John the Baptist, with the prospering port city, Puerto Rico-rich port. But that, says Nahiomy, is history.)

Cafe Cuatro Sombras

We start off by sampling some of the island’s very impressive small-batch, artisanal, shade-grown coffee. Café Cuatro Sombras offers a rich, cherry, chocolatey Cortadito (a shot of Espresso with milk) as the perfect complement to their sugar-dusted ham & cheese Mallorca roll with an incredibly decadent sweet ‘n sour oomph of guava butter.

A few blocks (and several history lessons) later, just as the mid-morning bake begins to set in, we stop for a bracingly tart and tingly, fresh-fruit popsicle at Señor Paleta – the 8-year old frozen treat store started by a pharmacist, his physicist buddy and a tricycle.

Beef Alcapurrias, Café el Punto

Continuing our crisscross jaunt along myriad pink, teal, yellow and dove grey buildings, we arrive at an artsy corridor between two houses bedecked with brightly colored yet alarmingly fierce-looking masks with horns, thorns and needles to gawk at while you savor West African Creole specialties at Café el Punto. Here I try my first (of what will turn out to be way too many) Alcapurrias – the most delectable gluten-free version of a fried empanada. The soft and buttery shell made from smashed yuca can be wrapped around just about anything from vegetables to crab to garlicky beef.

Creole Chicken Mofongo with rice & beans, Triana

At Flamenco hot-spot Triana, we roll up our sleeves to build our own Mofongo. After mashing the slices of sautéed plantain against ground garlic and butter with a wooden pestle and mortar, we insert a portion of Creole chicken before inverting the concoction out onto a plate. As the soft, and creamy textures combine with the ever-so-slightly spicy shredded chicken, we learn that in the absence of potatoes on the island, laborers would get their daily carb sustenance from plantains instead.

Chocolate Quesito, Casa Cortes Chocobar

And just like that, we find ourselves right in front of Casa Cortes Chocobar, home to Puerto Rico’s most beloved purveyors of confectionary. Not only does the Cortes family produce meltable hot chocolate bars as well as the ever-so-creamy-dreamy-chocolatey Latin cousin of a Cannoli known as a Quesito, but what I found to be sweetest of all are the insides of their chocolate candy wrappers that depict a series of collectible comics containing educational stories and lessons that help improve literacy and history amongst the islands’ children.

Buen provecho!