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A Visit to Old San Juan

Old forts take on a strong beauty in the Caribbean sunlight. I'm thinking, in particular, of the steep, enfolded bastion of San Cristóbal at the entrance to Old San Juan, how its precise angularity is softened by a centuries-old patina, how the cannon embrasures are set off by the radiance of the sky and the deeper, more languid blue of the sea. Basking in the heat, the battlements lie so peaceful and dignified that it's easy to forget their original purpose: killing.

Columbus discovered Puerto Rico on his second voyage, in 1493, but it wasn't until 1508 that the Spanish started a permanent settlement here; another 13 years passed before the settlers gave up their first malarial outpost and began building what today is Old San Juan. They had brought themselves to a spacious new world, but the world in their heads was still war-torn Spain, and they built what they knew. From the top of San Cristóbal you can look down over the result: though the island's green interior sprawls south and east, and a wide swath of sea stretches to the northern horizon, the city they constructed is a dense honeycomb of two- and three-story masonry buildings, threaded through with narrow streets and bounded by thick, outward-sloping walls.

Old San Juan today is a modern city in most senses: it has cars, television, T-shirt shops. Colossal cruise ships disgorge tourists who scurry to the Hard Rock Café and the Ralph Lauren outlet. But the symptoms of the 20th century are forgotten once you walk down the cobblestoned streets, beneath the wooden balconies, past the neat façades painted pastel blue, yellow, and pink.

If you stroll to the highest point in Old San Juan you will find a green-painted building that at one time served as the captain's quarters for the Spanish artillery. It's easy to understand the building's appeal to gunnery officers: on the roof they had a clear view over the entire city, from El Morro fortress in the west to San Cristóbal in the east to the whole expanse of the harbor lying southward. Today the building is the old city's only bed-and-breakfast, Galería San Juanbut everyone in town refers to it, after its owner, as Jan D'Esopa's. And if you happen to be, as I was, intrigued by the notion of finding out what lies behind the façades of Old San Juan, Jan D'Esopa's is the place to start.

D'Esopa, an effervescent, rather wacky American artist, runs her inn as a sort of crash pad. She has spent the last 36 years turning her Old San Juan house into a shrine to personal expression. In the sixties and seventies—so the story goes—Jan D'Esopa's was the scene of every kind of high jinks imaginable and unimaginable. Now that she's a grandmother, the fun has simmered down to a continuous happy hour, and those who jet in to enjoy her hospitality probably won't be unduly scandalized.

After greeting me with a glass of wine in her hand, D'Esopa gave me a tour of her rambling establishment. It's an agglomeration of several adjoining buildings, not atypical for the old quarter. When D'Esopa arrived in the early sixties, the area was full of whorehouses, flophouses, and thieves' dens. Had the neighborhood not been so poor, and so unpromisingly situated on a narrow peninsula, it would have been razed to make way for parking garages and office buildings.

Around the time D'Esopa first hit town, an energetic anthropologist named Ricardo Alegría had begun to flex his muscles as the founding director of a government agency called the Institute for Puerto Rican Culture. Back then most Puerto Ricans viewed Old San Juan as an eyesore, a threat to public morals, but Alegría devoted himself to preserving the area's cultural heritage.

Thanks to a law passed by the commonwealth legislature, the institute was able to offer tax exemptions on any building restored with historical fidelity. Thus began the slow transformation of a slum into a virtual living museum of Spanish Colonial architecture— emphasis on "slow." At first Alegría had a hard time convincing landlords that their decrepit and disreputable properties were worth fixing up, and so he enlisted Jan D'Esopa, a newly arrived gringa artist, to help him create watercolors of the buildings as they might someday appear: dappled in sunlight, with fresh paint and blooming trellises and happy faces in the windows.

D'Esopa doesn't have many of those paintings around anymore, but she does have plenty of her other work. In fact, the inn is crammed with four decades' worth of her paintings and sculptures. You can read her artistic stages like geological layers: now disembodied faces of clay, now bronze busts of politicians, now bas-relief scenes of semi-naked volleyballers. Since she tends to make duplicate casts of her works ad infinitum, you never know when you might come across a familiar piece repeated unexpectedly in an unexplored corner of the house, once, twice, or a dozen times.

The whole of Old San Juan stretches only seven blocks in each direction. It was built on a smaller, handmade scale, and no more than 15 minutes are required to walk its length. Strolls tend to be brought up short by the forts and massive walls that still bound the quarter on three sides. Time and again I found myself back at San Cristóbal, walking the battlements that look out over the water and the town. The fortress is designed not simply to repulse but also to embrace: instead of a single wall, San Cristóbal comprises seven successive lines of defense, each higher than the last, each convoluted and indirect, so that the invader overcomes the first line only to discover himself trapped in the next.

It struck me as an apt metaphor for the city itself. Having stumbled through the first gateway at Jan D'Esopa's, I found that the innermost recesses of San Juan remained a mystery, but a tangle of beguiling connections reached out from all directions. Everyone in Old San Juan seems to know everyone else. Walks down the street are slowed by an endless series of waves, hellos, and curbside conversations. Soon I was drawn in, too.

At a cocktail party before I left New York, I happened to meet an amiable Puerto Rican man who suggested I look up a friend of his named Isabel. A charming young lawyer, Isa not only agreed to meet me for dinner but offered to show me around town— all this sight unseen.

We agreed to meet at El Jibarito, a favorite restaurant among the locals. I arrived promptly, which left me with time to kill (in following the clock, as in many things, Puerto Ricans are a hybrid of Latin and Anglo-Saxon: they're always precisely a half-hour late). But waiting is never a chore in Old San Juan. Residents treat the quieter back streets almost as a communal courtyard, and it's entertaining just to watch the dance of life unfold. A group of men stand chatting on a corner. On a second-floor balcony an old woman appears, leaning on a walker, and looks down on the street. Salsa music seeps out from unseen apartments. A man and a woman cross paths, exchange a flying kiss, and hurry on.

At last Isa appeared, and we sat down at a plastic-topped table. El Jibarito demonstrates the first principle of Old San Juan restaurants: The less "authentic" it looks, the more authentic it is. The place with the old burnished-mahogany bar and sepia-tone photographs on the wall probably has a Paris-trained chef and a clientele from Miami. It's the little dives with the vinyl tablecloths, fluorescent lighting, and blinking Christmas bulbs around the molding that attract the locals. When he took our order, the white-mustached waiter thoughtfully removed the toothpick from his mouth and laid it on the table until he was done writing.

Over dinner, Isa and I talked about the many stories that have accumulated in the old city over the centuries. "They used to race horses down Calle Cristo," Isa told me. "One day, a horse couldn't stop at the end of the street, and the rider sailed off over the wall. He prayed to Jesus Christ to save him, was granted a miracle, and survived. That's why there's a chapel at the end of the street."

Having read that story in one of my guides, I told her: "In the book the ending is different. It says the man actually died, and the chapel was put up as a barrier to prevent further accidents. It'd be interesting to find out which is really true."

"No," she said with a laugh. "It's best not to know. The mystery is better."

After dinner we took a flying tour of San Juan by night, which is a very different city from San Juan by day. The tourists return to their cruise ships, the T-shirt shops shutter their doors, and out into the cool of the tropical darkness emerge the masters of the night. Young Puerto Ricans take their appearance seriously. The women,in particular, seem determined to make men's eyeballs explode. Perfect hair, perfect makeup; a tiny, clinging tank top; stretch pants that ride every curve down to a swoop of bell-bottoms; and in between—well, if the mission of the nineties is to perfect the abdominals of the world, then let the quest begin here, because San Juan is the Land of the Abs.

Isa and I made our way down Calle San Sebastián, poking our heads into the long line of bars where young people gather. The later it gets, and the farther down San Sebastián you go, the thicker the crowd becomes, so that by midnight on Friday or Saturday the intersection of San Sebastián and Calle Cristo is as packed as the floor of a discotheque, a jumble of bare torsos and fiery glances.

Turning left, we went downhill toward the harbor side of the city and the house of Mili Arango, matriarch of one of San Juan's more eclectic families. Arango, Isa told me, is one of Puerto Rico's best-known fashion designers, and a respected artist to boot. Her husband, a handsome and affable young man some 20 years her junior, happens to be a local rock star.

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