As the finishing touches of its restoration are applied, Old San Juan, Puerto Rico is emerging as the new Latin capital of America


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.

When we arrived at Arango's apartment building, Isa shouted up twice, three times, until finally a face appeared at the window"Hola!" Isa calledand down came a set of keys on a long string. Isa unlocked the steel gate, and we climbed the stairs to the fourth floor.

I had to shield my eyes when I walked in. The sprawling loft, which took up a whole floor, overflowed with whimsy—hand-painted kewpie dolls, lurid-colored shrines, weirdly anthropomorphic chairs—and though my memory may be deceiving me, the place seemed a kaleidoscope of shades of red, from fire engine to Chinese temple. On a zebra-skin couch, wearing a dalmatian-spotted dress, sat Arango's daughter Lisa, playing with her daughter, a baby dressed in black-and-white stripes. Arango herself, a blur of motion in a caftan, whisked in, said hello, and whisked out.

A houseguest, a young American named Kim, wandered over to chat. For three years, she told us, she had lived in Old San Juan, working as a masseuse; then, against her better judgment, she moved to L.A., where by accident she became a television personality. Even so, she said, she jumped at the chance to come back to San Juan and immerse herself again in Arango's extended family of bohemians.

She nodded as I admired the rambling array of artwork. "You have to come back here between ten and eleven o'clock in the morning," she told me. "The light—it's incredible."

People, i noticed, kept going on about the light. "I. M. Pei came here and fell in love with the light," said Sila Calderón, San Juan's newly sworn-in mayor, when I paid her a visit. "Every artist falls in love with the light."

I'm no expert, but there is definitely a lot of light in San Juan, especially at the height of the day, when the sunshine gushes down and bounces around those bold pastel buildings. No wonder they're painted such bright colors: they have to be, to compete with the fierce blueness of the sky.

Through Arango's friend the artist Victor Vázquez, I met Jorge Zeno, a painter, who offered to show me his studio. We met one morning at La Bombonera, a diner and pastry shop that functions much like the coffee shop in Seinfeld: everyone drops in at some point during the day.

We strolled down the street to Calle Cristo and rode the elevator to Zeno's rooftop home and workshop. "The light is perfect this time of day. Perfect!" he declared with a sweep of his arms. Through his patio doors filtered the clear light of a flawless sky.

Vázquez and Zeno both number among an informal group of young Puerto Rican artists whose work shares a playful exuberance, with a deliberately rough-hewn and childlike quality that draws some of its inspiration from the wildly colorful vegigante masks worn at Carnival time. Not everyone seems to get what their art is about.

"Critics!" he spat, when I asked him about its reception. "I am an outsider. The academy does not appreciate what I do." Outsider is perhaps too strong a word. As I got up to leave, Jorge passed me a hefty catalogue raisonné of his recent work, along with a brochure from a Christie's auction that pictured a work of his that sold there for $25,000.

After a while Old San Juan, apart from the architecture, doesn't seem very old at all. What had first struck me as an amazing re-creation of a Spanish colonial city proved to be less a restoration than an emphatically modern vision of an idealized past. For one thing, this distant outpost of a crumbling empire surely had never been so carefully tended. And what was being restored, anyway?If a building had been constructed in stages over the course of four centuries, to which century should it be returned?

These questions may sound academic, but for the people of Puerto Ricowho have spent the past century debating what exactly it means to be Puerto Ricancultural issues carry a heavy emotional weight. In fact, not long before I arrived in Old San Juan, just such a controversy was raging in the local newspapers.

The antagonists were the Catholic church and a newly refurbished hotel, then due to open shortly, called El Convento. The Catholic Church is no minor institution in Puerto Rico. From the earliest days of the colony, when little wooden ships anchored in the harbor after months at sea, the first thing their crews would do was march through the city gate, straight to the Catholic cathedral, to give thanks for their safe delivery.

Some time after the cathedral was built, a convent for Carmelite nuns went up alongside it. A grand structure, it had a spacious courtyard and a towering chapel. But eventually the convent's numbers shrank, until finally, in the early part of this century, the church gave the building to the city, which used it as a garage for garbage trucks.

It has answered other purposes as well. "This used to be the best whorehouse in Old San Juan," said hotelier Hugh Andrews proudly. A portly, cigar-smoking American who has lived in Puerto Rico for some 30 years, Andrews is the kind of perennial expatriate who could have stepped out of the pages of a Graham Greene novel. (In Vietnam he served in the army's recreation corps, setting up the resort that later became famous on TV as China Beach.)

After years of desuetude the old convent building was sold by the city of San Juan to the Woolworth family, which poured money into the property and opened it in 1962 as the El Convento hotel. The jet set loved it, but El Convento never made money, and in 1971 it was given back to the city in lieu of taxes. The property continued to decline. Finally, in 1995, Andrews, the man behind the ultra-fashionable El San Juan Hotel and the epic El Conquistador mega-resort, assembled a team of investors to buy the property.

Hoping to make El Convento a top-end hotel once more, they embarked on a vigorous rebuilding program. A wall was knocked down to open the courtyard to the street, and a casino and gallery of shops were constructed. The guest rooms, meanwhile, were kept segregated from the hustle and bustle of the public spaces, so that guests could enjoy a glass of wine by the miniature roofside pool without suffering the intrusions of window-shoppers. The result is an impressively luxurious, graciously old-fashioned hotel.

The church hated it. Members of the original order emerged to declare that the casino represented a desecration of the nuns supposedly buried beneath it. Ricardo Alegría also hated it, accusing Andrews of knocking down too many walls. Andrews is steamed at both of them for what he sees as irrational obstructionism.

The close quarters that make for a tight community also mean that squabbles flare with unusual vigor. Even for Old San Juan, the players happened to be located particularly close together: just as Hugh Andrews could look out of his office and shake his fist at the cathedral, Alegría could lean out his window and shake his fist at El Convento. Everyone else seemed to find it good entertainment.

By now i have spent enought time negotiating Old San Juan to realize that there was, in fact, a center to this labyrinth. Behind it all one man seemed to be lurking. Every discussion of the old city's history invoked his name; every controversy over a demolition or construction featured him as a character. Ordinary Puerto Ricans spoke of him with the sort of reverence usually reserved for martyred revolutionaries.

Ricardo Alegría is old now, a stooped and frail 76, and he has been retired from the Institute for Puerto Rican Culture for 23 years. In his youth he made headlines when he discovered ceremonial ball courts built by the vanished Taino Indians, similar to those used by the Aztecs. For decades he oversaw the painstaking process of rebuilding Old San Juan. Along the way he helped revive dying Puerto Rican handicrafts, including the santos figurines that feature so prominently in the tourist shops on Calle Cristo: every single one made nowadays was carved by an artisan trained by the Institute for Puerto Rican Culture. He is often, and without irony, referred to as the Father of Puerto Rican Culture; and while he has many enemies, there are few who don't respect, no less cherish him. Even Andrews had to admit that if it weren't for Alegría, there wouldn't be an El Convento hotel to argue about.

But Alegría's health has been poor, and his schedule is still busy, so meeting him proved difficult. After a week I had heard no word. It could have been worse: Hugh Andrews had been waiting eight months to arrange a powwow.

"Get Jan to take you," Andrews finally advised. "And whatever you do, don't mention my name."

Evidently, Alegría has had a crush on Jan for years. And so the doors, long shut, swung magically open, and the two of us tramped down to his office.

Too energetic to slow down after his retirement, Alegría had immediately founded a research institute called the Center for Advanced Studies on Puerto Rico and the Caribbean. Laid out around the enormous central courtyard of a former seminary, the place is as dignified and rambling as the old man's career.

Jan and I were summoned to a meeting room where massive high-backed wooden chairs stood around a black hardwood table. Don Ricardo shuffled in. His white hair was slicked back; great swooping white eyebrows hung over his eyes like summer clouds. He greeted us warmly and bade us sit. I asked him about his long years of work in San Juan.

"There was a time," he recalled, "when progress meant demolition. Progress meant chrome and plate glass and skyscrapers. Architects and merchants said I was stopping progress because I wanted to preserve the spirit of the old city." He added, with pride, "Now they see I am right."

He recounted his various struggles with the government and bits of historical lore. Casting a twinkling eye at Jan, he recounted the story of the Spanish army officer who set his mistress up in a house below the fortress walls, connected to his quarters by a subterranean passage. Then, growing restless, he pushed himself to his feet and announced that he would give us a tour.

He led us through the shaded cloister to a newly restored chapel with a magnificent trompe l'oeil rotunda, and then to an old kitchen with a large fireplace and hanging iron pots. At last we reached the very back of the seminary. A pair of huge black doors stood in the shadows, heavily padlocked. Don Ricardo led us around through an antechamber to a smaller side door, which he unlocked, and we passed into the startling light of afternoon.

It was a secret garden, tucked between the ancient buildings like the hidden compartment of a suitcase, lush and overgrown and dominated by a towering mango tree. Jan's mouth fell open in wonder: she had spent decades wandering up and down the surrounding streets without guessing that such a place existed.

Ricardo Alegría, the wizened gardener of all that Old San Juan had become, stood smiling amid the tangle of shoots and vines glowing in the sunlight. I asked him about Isa's mystery, the horseman of Calle Cristo.

"Historians say he was killed," he said, nodding. Then he added: "I like to believe he was saved."

  • La Fortaleza the palatial fort turned governor's mansion.
  • Museo de las Americas wonderful cultural exhibitions in newly renovated former military barracks.
  • San Juan Cathedral the resting place of the quixotic explorer Juan Ponce de León.
  • Casa Blanca the former home of the Ponce de León family, with a beautiful garden.
  • Paseo de la Princesa the recently restored promenade where locals stroll away the evening hours.
  • Parrot Club for dinner among the old quarter's swankiest young people.

Old San Juan is about a 20-minute drive from Luis Muñoz Marín International Airport. Once there, you're within walking distance of everything you need. (Except for a beach— the nearest one is in Condado, 10 minutes away by taxi.) People take pride in their appearance. Men should wear trousers, especially at night; women, pants, a skirt, or a light dress.

Hotel El Convento 100 Calle Cristo; 800/468-2779 or 787/723-9020, fax 787/721-2877; doubles $315. A historically evocative boutique hotel with the grace of monastic life but not the asceticism. It has 57 small but comfortable rooms for guests, who can enjoy breakfast on the patio and take a dip in the rooftop mini-pool.
Galería San Juan 204206 Calle Norzagaray; 787/ 722-1808, fax 787/724-7360; doubles from $95. Better known as Jan D'Esopa's, this Old San Juan institution has evolved over the course of nearly four decades as its innkeeper has joined together adjacent properties and renovated them. Every square inch is covered in D'Esopa's artwork, which she'll sell you straight off the wall.

Chef Marisoll 202 Calle Cristo; 787/725-7454; dinner for two $100. (Prices do not include drinks, tax, or tip.) Puerto Rico's first female executive chef—formerly of the Condado Plaza—presents classic European cooking with subtle island touches. Curried chicken served with basmati rice and Indian papadums share the menu with prosciutto and Manchego cheese in white-truffle oil.
Parrot Club 363 Calle Fortaleza; 787/725-7370; dinner for two $50. Since it opened last year, this has been the place to be seen for San Juan's fashionable set. The "Nuevo Latino" kitchen is surefooted: curried crab cakes, tender marinated ribs, seafood seviche.
Il Perugino 105 Calle Cristo; 787/722-5481; dinner for two $100. The toniest of Old San Juan's dining spots (request a table in the covered courtyard and try the scallops bathed in tomatoes, mushrooms, and butter sauce).
La Mallorquina 207 Calle San Justo; 787/722-3261; dinner for two $50. The oldest Puerto Rican restaurant in San Juan, and probably the best known.
La Bombonera 259 Calle San Francisco; 787/722-0658; lunch for two $16. The pink banquettes and the waiters in red jackets and black bow ties make it look like a fifties lunch counter. The food is cheap and authentic: order the marinated roast pork and fried plantains.
El Jibarito 280 Calle Sol; 787/725-8375; dinner for two $20. Locals come to this joint for meals like the ones mami used to make. The simplest dishes, such as lamb stew, are the best.

Aquí Se Puede 50 Calle San Justo. Island music performed live most nights. On Tuesdays, opera.
Violeta 56 Calle Fortaleza; 787/723-6804. Wood beams and ceiling fans lend this bar a colonial charm.
El Batey 101 Calle Cristo. Dark and graffiti-filled, but a required stop for anyone making the ritual tour of the bars along Calle San Sebastián and down Calle Cristo.

El Alcazar 103 Calle San José; 787/723-1229. This antiques shop, recommended by Ricardo Alegría, has a fine collection of old handmade santos figurines.
Galería Botello 208 Calle Cristo; 787/723-9987. Art by Jorge Zeno, Victor Vázquez, and others.
Luigi Marrozzini Gallery 156 Calle Cristo; 787/725-2840. This third-floor walk-up gallery features individual artists, including Mili Arango.

Adventure Guide to Puerto Rico by Harry Pariser (Hunter Publishing)How to explore the rain forests, beaches, and water by bicycle, foot, car, and boat.
The House on the Lagoon by Rosario Ferre (Farrar, Straus & Giroux)The rise and fall of a wealthy family provides a crash course in island history.
—Martin Rapp

On the Web
Welcome to Puerto Rico ( ) Solid tourist information and a picture-rich Old San Juan section.
—Mark Orwoll