Author Nicholas DeRenzo Photography Gabriela Herman
DAY ONE If you’ve ever wanted to feel like a well-to-do conquistador, you could do worse than booking into the Hotel El Convento. The property is set in a mid-17th-century Carmelite nunnery, its rooms decked out in Colonial style, its courtyard shaded by a 300-year-old Spanish nispero tree, its windows opening onto the waterfront and the multicolored jumble of Old San Juan. Just beyond the bay is the Art Deco Bacardi distillery. I can’t help but feel that this trifecta—history, sea, rum—may come to define my trip.
It doesn’t seem prudent to start on the rum so early, so I begin my day by exploring history instead. To help me unpack the secrets of Old San Juan—set on a jam-packed, three-square-mile island—I’ve recruited Lady Lee Andrews, a 43-year-old local poet with cascading braids and curls. “I’m a born and raised sanjuanera,” she says, as we hug hello on the steps of the hotel. “I’m like a tree. I’m rooted here.”
Before we even begin our stroll, we encounter local legend Saúl Dávila, who famously wanders the streets selling armfuls of azucenas (white lilies). “This man here walks miles every day selling flowers, and he’s been walking since I was a little girl,” Andrews says as she buys a bunch. “We’ll give these away as we go.”
We cross the street and head into the Cathedral of San Juan Bautista, the second-oldest church in the Americas (after the basilica in Santo Domingo, Dominican Republic). The original structure was built in the 16th century, though Andrews is quick to point out that, due to centuries of being pummeled by hurricanes, only the front steps are original.
These vicious storms, Andrews continues, have left a mark on the city’s people as well. “With hurricanes, there’s a sense of kinship,” she says, laying a flower at the feet of Our Lady of Divine Providence, Puerto Rico’s principal patroness. “When I was a little girl, I longed for September hurricane season, because all the neighbors would come out and help each other. It breaks that pattern of everyone being in their own worlds.”
Outside, the narrow colonial streets of the casco, or Old Quarter, are a riot of color, down to the bluish cobblestones, made with iron furnace slag and once used as ballast on Spanish ships. Lining the roads are stucco houses, many with wrought-iron balconies, painted lime green and banana yellow, guava pink and papaya orange (think New Orleans’ French Quarter with the volume turned up). Interestingly, these bright hues are a relatively new addition to San Juan; the city government used to dictate permissible paint colors, and the palette was surprisingly muted.
We pass a mural of the azucena man and his trademark bouquet of lilies and duck into Restaurant Siglo XX, a small traditional diner that’s been around since the mid-1950s. At this time of day, the obvious choice is a mallorca, a sweet bread roll stuffed with ham and cheese and crowned with enough powdered sugar to make a beignet blush.
I’ve noticed that Andrews can barely walk a block without stopping to hug someone, though she insists that this says more about the neighborhood’s character than her own. “The first time I went to France to visit my husband’s family,” she tells me as she stirs brown sugar into her café con leche, “I was shocked that he had lived in the same house his whole life and didn’t know his neighbors. So, being the Puerto Rican that I am, I went over, banged on the door, and said hi. And now, 18 years later, they’re best friends.”
Our casco walk takes us past chattering wild parrots fighting over a pizza crust near the port and the baby-blue facade of La Fortaleza, a 16th-century fortification that serves as the governor’s residence. At the end of the cliffside Calle del Cristo sits a tiny, age-mottled chapel, which has a story: This street once hosted dangerous horse races, in which the rider who got closest to the edge would win. One man plunged over and miraculously survived the fall, and local residents went on to build the Capilla del Santo Cristo to thank God.
We continue down Calle Fortaleza, past Barrachina, the restaurant where the piña colada was invented in 1963, and duck into Andrews’ shop, Mi Pequeño San Juan, where she and her painter husband, Nicolas, create plaster replicas of local landmarks. Around the corner from here is her café, the Poet’s Passage, its counter modeled after a roll-top desk, with slips of paper and pens on each table in case the spirit moves you. There’s also a chihuahua named Federico García Lorca, a green parrot named Pablo Neruda, and a lovebird named Robert Frost. Another bird, Maya Angelou, died a couple of years ago—coincidentally, at around the same time as Maya Angelou the poet.
I say goodbye to Andrews and head to the Museo de Arte de Puerto Rico, which is housed in a 1909 neo-classical hospital with a contemporary annex. While outside the limits of Old San Juan, it’s an institution steeped in history. Like the building, the museum’s Laurel Kitchen/Art Bar plays with the theme of old-meets-new. Here, Next Iron Chef contestant Mario Pagán lovingly remixes the flavors of his homeland.
“We’re all about the pork,” he says, dishing up pig-ear crackling with tamarind sauce and plantain mofongo. So begins a cascade of courses that include brie croquettes with papaya skin preserves; lamb alcapurrias (fritters) with mint pique aioli; pegao (crispy rice that sticks to the bottom of the pot) with blood sausage, caramelized fennel, avocado, and egg white; black Chilean sea bass with truffled yuca puree and a port wine and foie gras sauce; and, for a finale, a slab of guava goat cheesecake. “I hope you’re going to take a long nap after this,” Pagán says with a grin.
But no rest for the gastronomically weary. I’m meeting the museum’s Venezuelan-born curator, Juan Carlos López Quintero, for a tour. The museum is organized according to themes rather than chronology—“You have 18th-century paintings next to photographs next to video installations”—which makes for a lively experience. It seems fitting that the first gallery we enter, after such a gluttonous lunch, is “Plátano Pride”—a collection of artworks celebrating the island’s staple starch, including a portrait of a boy wearing a life-size gold plantain on a chain around his neck.
“The plantain has been an icon of Puerto Rican art since José Campeche,” López Quintero says, leading me to the master’s 1797 portrait of the governor’s two young daughters. “For the first time, you have elements that belong to this country—the maracas, the pineapple.” I’m particularly taken with a massive triptych nearby called The Garden of Intolerance by Arnaldo Roche Rabell, a local neo-Expressionist painter whose swirls of thickly applied paint call to mind a tropical van Gogh. It also seems a perfect representation of the island’s noise and humidity and color—the “muchness” of Puerto Rico.
I find my appetite inexplicably whetted, so I drive a few minutes to Jose Enrique, an unassuming eatery set in a bungalow on the lively square La Placita. Enrique trained at the Culinary Institute of America, and was the first Puerto Rican chef nominated for a James Beard Award. He personifies a new wave of chefs here, but his hearty rustic fare—rice and red beans, tripletail fish fritters, deep-fried skirt steak topped with fried eggs, coconut pudding—would satisfy the most ardently traditionalist abuelita.
Before bed, I stop for a drink at La Factoría, whose pocked walls and dim lighting call to mind the kind of place where (heavily tattooed) revolutionaries might have gathered to talk shop. The feeling of intrigue is heightened by the nesting-doll layout, with different bars extending beyond a succession of unmarked doors. I sit beside a wall inscribed with “Hijos de Borinquen” (Borinquen being the island’s pre-Columbian Taíno name) and sip a De Lo Mejor, a cocktail of housemade horchata, tequila, Cointreau, lime, and a smoky local rum, Ron del Barrilito.
This hip speakeasy vibe is spreading. Just next door is La Cubanita, a new bodega-inspired cocktail bar (its shelves ironically stocked with saint candles and bottles of Clorox) where you can order spirits mixed with fresh juices. My Guayabera (Barrilito, guava, lime, and sugar) is a great drink but a terrible nightcap, in that it makes me want to go dance the merengue rather than settle down. But it’s been a long day. Maybe tomorrow.