For 123 years, Puerto Rico has walked a wobbly line on the Caribbean edge of America. It is still commonly mistaken for a foreign territory. But as a once-in-a-generation cultural and political awakening has swept the island, Puerto Rico has swung dramatically from castaway to contender to become the first new state since Alaska and Hawaii joined the U.S. 62 years ago.
World-class restaurants and bars have brought modernism to San Juan, the second-oldest colonial capital in the Western Hemisphere, a mirror of Spanish Imperial cousins such as Havana and Cartagena. And years of turmoil—hurricanes, earthquakes, political protest—have recently jolted the island with a newfound electricity of identity. That spark has reignited the criollo melting pot of 3 million people, which is hot enough to melt hearts as well. The beaches, rainforests, and surf towns that have drawn visitors for centuries are still there, of course, but after 500 years, Puerto Rico is now firmly focused on its future, and the paradise of possibilities that await.
Day 1
Castles, chocolate, and tchotchkes in Old San Juan
I begin at the beginning: Old San Juan, with its pastel splendor of Spanish colonial buildings along alleys of metallic blue cobblestone first settled in 1509. My hotel, Palacio Provincial, is a history lesson in itself, having been the site of the first Puerto Rican parliament and later Puerto Rico’s Department of State before being reimagined this January as a boutique property welcoming folks who are decidedly less stately (ahem, me).
I wake up starving, so I’m grateful that first on the docket is a neighborhood food tour with Spoon. I realize this is going to be a history lesson as much as a culinary one the moment I meet my guide, Pablo Garcia—nicknamed WikiPablo—who regularly quotes historical documents dating back centuries. (My favorite is the colonial navigation from Europe to Puerto Rico: “Sail south until the butter melts, then turn right.”)
The tranquility of our meeting spot belies the wild history at our feet. We’re standing by a tall granite and ceramic column dedicated to the island’s indigenous people, at the tiered Plaza del Quinto Centenario, which commemorates San Juan’s 500th anniversary, and the 16th-century colonial fortress of Castillo San Felipe del Morro, which juts out on a promontory like a proud chin. In the surrounding meadow, where Sanjuaneros now fly kites, an obelisk marks the closest the Dutch ever came to the fortress before giving up their invasion in 1625 (after Sir Francis Drake’s failed invasion in 1595). A jarring Moorish Revival lighthouse pokes out, first erected in 1846 but rebuilt in 1908 after being destroyed during the Spanish-American War. It’s a modest site, more fortress than castle, but enough battlefield victories make anyone feel regal.
We dip into Cuartel de Ballajá, the old barracks, which now houses the Museum of the Americas and, more important for our tour, the fourth generation Don Ruiz Coffee Shop.
Emboldened by the strong brew, we make our way into the narrow lanes of the Old City, passing a statue—made of repurposed cannons from Britain’s failed 1792 invasion attempt—of Puerto Rico’s first governor, the conquistador Juan Ponce de León. (He was replaced by Diego Columbus, Christopher’s son.)
A popular legend disputed by historians is that Ponce de León left to search for the Fountain of Youth, and while WikiPablo can’t take me there, he does introduce me to the next best thing: Chocobar Cortés, a long-lines-all-day shop that sells products from a 92-year-old, family-owned chocolateria. We indulge in decadent chocolate bars that take us back to our childhoods. And, as a reward for adulthood, icy chocolate martinis, kissed by Baileys. Yes, for breakfast. Very yes.
The tour continues. I devour a bowl of mofongo at Hecho en Casa, a beermosa (which includes rum) and an incredible local twist on a Cuban sandwich at La Taberna Lúpulo, and too many other nibbles to list (with dignity). “I love that we live in the future,” WikiPablo cheers. “A world without hot sauce is 1491.” Belly full, I part ways with WikiPablo and stroll for a while on the sunny sides of the streets. (As my guide informed me, the streets and buildings in Old San Juan were designed so there’s always a sunny side.)
I stick close to Calle de San Francisco, the district’s main artery, but there are so many offshoot lanes and alleys with come-hither curiosities: a bold mural here, a flowery balcony there. Rounding a corner of the city wall, I stumble upon Casa Estrecha (the Narrow House), a slender, bright yellow home that, at just 5 feet wide, has an almost magical Platform 9¾ vibe.
Old San Juan is the historic core of the city, and also its souvenir core—although the glut of trinkets is far more fun and wondrous than tacky. I like things with a bit of mystery or poetry to them, so I can’t resist The Poet’s Passage, where I pick up a map of the island for a Puerto Rican friend back home in New York. At Mundo Taíno, I wish I could buy one of the striking indigenous vejigantes (unwieldy spiky folkloric masks that are popular during Carnival but too big to cart home in my carry-on). And at Mi Pequeño San Juan, housed in the birthplace of Luis Muñoz Marín, the first elected governor of Puerto Rico, I examine the ceramic miniatures of Old San Juan’s famous Spanish colonial doors to see if I recognize any from my time today.
The heat is beginning to take its toll, so I cool down with a piragua, a shaved-ice treat sung about in Lin-Manuel Miranda’s other musical, In the Heights. There are little street carts selling it everywhere, and after a few bites of a passion fruit one, I too feel like dancing and singing in the streets.
That’s what modern Puerto Rico is about: finding comfort where maybe you didn’t expect it.
I start to wander back to my hotel but stop into one last shop, the elegant Pure Soul, where owner Sylma Cabrera has pulled together apparel from around the world, accessories from more than 200 local designers, and her own vibrant linen dresses, blouses, and menswear. “I want people to know they can be comfortable in style,” she tells me as I ponder a braver, bolder wardrobe. “That’s what modern Puerto Rico is about: finding comfort where maybe you didn’t expect it.”
Over a cocktail beside the rooftop pool back at the Palacio, I think about Sylma and how 21st-century life flows through this 16th-century mural of a town. In search of a bridge between centuries, I leave Old San Juan in favor of the 102-year-old Condado Vanderbilt Hotel in Condado, the Ibiza of San Juan. Enough of the city’s past—I want to teeter on the edge of its future.
Feeling suddenly modern, I try something almost heretical: the avant-garde cuisine of executive chef Juan José Cuevas’s 1919 Restaurant, at the hotel. Cuevas is the first Puerto Rican chef to earn a Michelin star, and his philosophy of “flavor without distraction” has sent him down paths as unexpected as, for example, an espresso risotto. He recommends the “chef ’s table,” which is basically an improvised tasting menu. “I just take a piece of paper and do it by hand, of the moment,” he explains. “The amount of energy you get back is the best. The more chef’s tables out there, the more energy I get.”
The energy shows: a shot glass of coconut-cucumber gazpacho; creamy polenta soup with truffles and codfish croquettes; salmon softer and richer than butter (I cry out with gustatory joy when I take a bite, and three other tables look at me); wild purslane with organic mushrooms and cassava juice; cochinillo (suckling pig) with caramelized onions; grilled short ribs on a bed of creamy parsley with potato churros; a dessert called “chocolate decadence” that lives up to its name. There are actually three desserts, four petit-fours, and a farewell loaf of banana bread. Can you imagine his Thanksgiving spread?
Feeling gluttonous and a bit buzzed from the wine pairings, I know I should get to bed, but a devil on my shoulder reminds me I forgot to visit Old San Juan’s La Factoría, which some people know because it was ranked number 32 on 2019’s The World’s 50 Best Bars list, and other people know because it was the location for the bulk of the interior party shots in the music video for “Despacito.”
The insides of the club are cavernous—room after room, each nook substantial enough to be a bar in its own right—but fortunately I find one of its owners, Leslie Cofresí, out front. Cofresí would never say this, but he’s pretty much the unofficial mayor of San Juan’s nightlife. We clink his signature cocktail, a Lavender Mule, but I pass on the 25-ounce take-home bottles for sale. “Too much of a good thing,” I say.
Cofresí pretends not to understand, but his smile gives him away. “Tomorrow, I will take you to real Puerto Rico,” he tells me. “Be ready.”
Day 2
Contemporary art, beachfront piña coladas, and lip-sync battles
Along hip Calle Loíza, I pass makeshift walls of books offered free to the community as I wend my way to Santurce, the city’s arts district, and Kamoli, a café and design shop that feels as if it’s run by Chrissy Teigen and Stevie Nicks. After a coffee and a lemony salad of avocado, cucumber, quinoa, and spinach, I sally forth.
I wander onto Calle Cerra, a stretch of street lavished with murals: trippy psychedelia, whimsical geometry, and tributes to everyone from Spike Lee to Ismael Rivera, a legendary local singer. There are lots of playful and political riffs on the Puerto Rican flag, but also graffiti as goofy as a lawn gnome in sunglasses flashing a peace sign.
Melting in the heat, I dip into El Patio de Solé for a quick mango smoothie but linger in the space, a kind of Puerto Rican Narnia that seems impossible on the other side of such a simple entrance. It’s a madcap art gallery in its own right, and I’m tempted to camp out here a bit, but I’m late for a date.
I meet Naíma Irizel Rodríguez Rivera—who runs a local theater company, Teatro Breve, and a cultural events space, Pública—at the Museum of Contemporary Art. After a quick introduction, I discover that Cofresí, the La Factoría co-owner, is her boyfriend, which makes her, effectively, San Juan’s deputy mayor.
So much of the art at the museum is nudity, in the sense that the works show the Eden of Puerto Rico without fig leaves: candid anger, fearlessness, romance, torment, and vulnerability—the Puerto Rican heart laid bare. There’s Dhara Rivera’s Palingénesis, a storm shelter filled with a tribute to the island’s botanical diversity; Sebastián Gutiérrez’s Comfort Zone, a portrait in which the face’s lips and eyelids can be opened by curious, handsy viewers; and a simple, untitled landscape painting from 1936 by Luisiña Ordóñez, which the artist describes as “the inner ecstasy of her sensibility.” Rodríguez and I don’t get that deep, although at one exhibit we each talk to an ATM about our identities and our values before it spits out some money. I get $5. She gets $6.
Unfortunately, there are also a lot of video works of dance. I say unfortunately because it inspires Rodríguez to give me an impromptu salsa lesson. The less said about that lesson the better, but it’s safe to assume the museum’s curators are not aching to enshrine my performance in their collection.
“There’s a phrase in English,” I offer, but Rodríguez is far ahead of me: “Two left feet,” she says.
“Yeah,” I reply. “I think I have three.” After all that walking and dance-like motion, I’ve earned a big lunch, so I head to meet José Enrique—the first Puerto Rican chef to be nominated for a James Beard Award—at his eponymous diner a few blocks from my hotel.
“Can you cheers deviled eggs?” I ask. Enrique shrugs. “We just did.” We laugh, and he continues. “I love eating my lunch bigger than my dinner. It makes sense to eat better during lunchtime.” He then proceeds to make a lot of sense: elegant cod fritters, skewers of smoked pork, a pumpkin and beet salad, and filet mignon with mamposteao (rice and beans that is a translational offshoot of “masonry” for its ability to fortify).
All I want to do after that meal is sit and rest. Luckily, San Juan has a place for that: the beach. There are plenty of strips of sand here, and I choose a small roadside one that shows up in Google Maps as “buen spot” with two flame emojis. Before that, though, I swing by Caribe Hilton, the first Hilton built outside of the 48 states and, in 1954, the birthplace of the piña colada. I have just one, but if you need an excuse for a second, La Barrachina, a restaurant in Old San Juan, also claims to have invented the island’s official cocktail (albeit in 1963).
Drink in hand, I kick off my Converses and splash around a bit before finding a shady palm tree to lie under. Did I nap? Or is this place just that dreamy? Either way, I’m lost in the moment, watching waves lap the island’s crumbled fortifications, when Cofresí’s Jeep pulls up, with Rodríguez riding shotgun, to whisk me off to the countryside. After an hour of winding single-lane roads—more like trails—we pull up to a huge, barn-like, red-and-green farmhouse on the shore of a lake. This is Bacoa Finca + Fogón, a community-minded restaurant specializing in wood-fired cooking that plays on the Puerto Rican tradition of bonfire feasts in the woods.
We take a table outside, on a covered deck, and devour dish after dish. The green plantain tostones with cream and caviar and the chicharrón with citrus horseradish gremolata are addictive, but the whole red snapper with pickled chayote takes the cake. Speaking of dessert, there’s a pumpkin and sweet potato pie that leaves me light-headed. The chefs—Raúl Correa, Rene Marichal, and Xavier Pacheco—join us, and the whole meal is spiced with bawdy banter and unprintable jokes. Plates cleared, we dance—yes, even my three left feet—swirling as playfully as the cigar smoke.
I peer through a window shaped like a lopsided heart into the Pepto-pink interior. Wowza.
When we get back to San Juan, we decide to keep the party going at Loverbar, an LGBTQ hangout with a relatively strict velvet rope. I peer through a window shaped like a lopsided heart into the Pepto-pink interior. Wowza.
Once inside, we see a lot more. Cupcakes. A dog napping on a couch. Drag artists locked in fierce lip sync battles assailed with dollar bills sailed toward their feet in the form of paper airplanes. Shot glasses in our hands. Empty shot glasses. Finally, I see the time and realize I need to go to bed.
Day 3
A rainforest hike, a spa indulgence, and an illuminating kayaking trip
The trip to Bacoa reminded me that I’m here for the whole island, not just the city. To kick off a day of natural wonder, I dip into the Dreamcatcher, a surfer-chic beachfront hotel with mellow kibbutzy vibes, for a three-course vegan breakfast that starts with an apple-pie parfait, which consists of spiced almond mousse with oat streusel, chia pudding, and caramelized apples. Served like that, an apple a day sure does keep the doldrums away.
I take a car about an hour east, ready to explore the majesty of El Yunque, the only tropical rainforest overseen by the U.S. National Forest Service. First, though, I drop my bags at The St. Regis Bahia Beach, a 400-acre resort on a former coconut plantation. It’s a tranquil oasis that reminds me that the native Taíno gave English the words “canoe” and “hammock.”
In the lobby, I meet Ashley Perez, the resort’s environmental scientist (a perk that’s owed to the property’s status as an Audubon Society sanctuary). As we drive to the park and then continue on foot, she gives WikiPablo a run for his money, explaining everything from flammable tree sap (so that’s why it’s called candlewood!) to iguana tracks. She points out lizards, parrots, a red-tailed hawk, and even two mating snails.
Perez instructs me to be on the lookout for enormous champion trees and a tiny, 4-centimeter-tall orchid that grows on moss-covered trunks. It was endangered—numbering just 140 in 1991—but last year was proposed to be taken off the endangered list after a count of 3,000. I ask what it’s called, and she tells me its scientific name, because “there is no common name.” I see an opportunity: “Can it be called the Taneko orchid?” I ask, explaining that its namesake, my 2-year-old niece, is the tiniest human I know. She laughs and promises to suggest it to the proper scientific authorities.
At the end of a decent hike, we reach a waterfall where a family is scrambling around on the rocks. A little boy in just a diaper sees me looking a bit tired and gives me a thumbs-up. I reply with my own, and he counters with two thumbs up. I respond in kind, so he raises his two thumbs as high as he can. Scared of his infant brinksmanship, I decide to bow deeply. He laughs and claps, giving me the energy to continue. I’m glad he did, too, because I’m soon reveling in breathtaking panoramas of what feels like the whole island: forests and mountains punctuated by villages and towers, stretching toward the beach, the sea, the horizon, and the imagination. Yunque means anvil, and, wow, do I feel steadied by it.
I return to the St. Regis to steam and sweat out the aches from hiking in the spa. There’s an 11th-hour challenge ahead, so I get a massage that kneads me into relaxation while making me smell like starfruit (“Because you’re a star!” says my masseur). I linger, aprèsstar, in a poolside cabana and then freshen up in my room’s immense rain shower, which is large enough for an adult to do jumping jacks in. Hypothetically.
Is it monstrous to follow a meditative day of rainforest treks and spa tranquility with a barbecue dinner? Because that’s exactly what I do at La Estación, a converted gas station in nearby Fajardo. Just to be safe, I start with corn-battered lionfish, an invasive species. (Every little bit helps.) I do my best to devour El Matahambre, “the hunger killer” sandwich, but the pile of meat and cheese is really meant to serve two… families… of velociraptors. I never would have guessed my Puerto Rican vacation could mingle with my North Carolina childhood, but that’s the magic of barbecue.
A few minutes’ drive away, I’m at the island’s eastern shore for that 11th-hour challenge: I’m going to kayak solo—well, with a Kayaking Puerto Rico tour group, but in my own kayak—to a bioluminescent bay, where microorganisms have evolved to emit light when disturbed.
It’s a big deal for me, because I don’t really know how to swim. Also, I’m a Trekkie, glowing plankton is pretty alien, and I’m never going to see the bioluminescent waterfalls on Gedi Prime.
As I paddle against the current, through a mangrove swamp that slowly darkens to pitch black, I have an epiphany: It’s scary—and beautiful and awkward and romantic and difficult and calm. Like this island, and like me, travel can be all these things at once. When I get to the bay, under the glittering stars, I run my hands through the water and trigger the legendary blueish spark. Even after unprecedented hardship and isolation, Puerto Rico still has its glow—and, it turns out, so do I.
Next Up: Three Perfect Days in Belize
