Within the space of 10 minutes during one recent San Juan sunset, I walked along the fat ocher stones of a centuries-old fortress, passed through a garish strip mall with an ocean view, and ended up at a romantic Italian restaurant. I went in, of course, and ate well, surrounded by Renaissance images. At the next table a family spoke rapidly in Spanish; then the eldest daughter stood and made a toast in crystalline English. Her bilingualism shed some light on this mysterious city, a distinctive blend of Caribbean and Latin American cultures that has also absorbed and transformed Uncle Sam's considerable influence. Mainland tourists will feel both at home -- what with the English-language newspapers and Walgreen drugstores -- and as if they are somewhere far away. This is, after all, a city of lush foliage, dark late-night bars throbbing with tropical sounds, and endless beaches where a coco frío is never far from reach.
Related: Best Hotels in Puerto Rico
where to stay
Which hotel you should choose depends on what you're after. The resorts of Isla Verde -- with casinos and all the amenities that anyone could want, except golf -- front a broad, dreamy beach. Non-ocean-view rooms, however, generally overlook the airport, and there isn't much to do outside the resorts. Old San Juan has hotels that are more eclectic, but they're a 20-minute walk from the beach. The area does, however, have the city's best stores, museums, restaurants, and strolls. Condado, with the look and feel of Miami Beach, is not as inviting as it used to be (and the undertow can be dangerous).
El San Juan Hotel & Casino 6063 Isla Verde Ave., Isla Verde; 800/468-2818 or 787/791-1000, fax 787/253-0178; doubles $345-$495. It's rare when Hollywood set-decorating techniques result in such an inviting rococo atmosphere. Improbably, the overuse of murals, marble, gilt, and candelabra make the soothing, dark interiors the most inviting on Isla Verde, even while they remind you of Liberace's boudoir. The service suggests that someone actually cares, and the mammoth pool and grounds are done in full tropical splendor. The restaurants are frequented by locals as well as guests.
Ritz-Carlton San Juan Hotel & Casino 6961 State Rd. 187, Isla Verde; 800/241-3333 or 787/253-1700, fax 787/253-1777; doubles from $400. The lobby oozes easygoing affluence, from the Puerto Rican women in frilly dresses sharing an elaborate tea while talking on their cell phones, to the business travelers trying to close a deal as the pianist tinkles out "Close to You." Everything is done in pretty, light colors, and the employees are prone to smiling as you pass. Hang out at the spa -- for beauty treatments, yoga, fitness classes -- or on the beach right out the back door.
Hotel El Convento 100 Calle Cristo, Old San Juan; 800/468-2779 or 787/723-9020, fax 787/721-2877; doubles from $313. On the top floors of a converted 17th-century convent, the 58-room El Convento has an intimacy and luxury not found in the large resorts. Guests enter their rooms from balconies over the courtyards, and from most windows you can see the old city and the harbor. Breakfast is served on the terrace, a few steps below the small plunge pool and outdoor spa tub overlooking the water.
La Galería San Juan 204 Calle Norzagaray, Old San Juan; 787/722-1808, fax 787/724-7360; doubles from $95. At the highest point of Old San Juan, artist Jan D'Esopo has turned several buildings -- linked by stone patios and public areas -- into an eccentric hotel. From the roof decks, you can see the whole of San Juan, old and new. Tropical birds chatter back and forth, and the owner's artwork is everywhere (and for sale). If you're splurging, go for the recently constructed suite with terrace and ocean-view spa tub.
El Conquistador 1000 Conquistador Ave., Fajardo; 800/468-5228 or 787/863-1000, fax 787/253-1078; doubles from $375. An hour's drive east from San Juan, the massive El Conquistador has everything -- golf, tennis, beaches, swimming pools, restaurants, great rooms -- except a sense that you're in Puerto Rico. That said, there are incredible views of the islands of Vieques and Culebra. At the hotel's private Isla de Palomino, you can walk the secluded beach, ride horseback, snorkel, or ply the waves on a kayak or sailboard.
San Juan is divided into many neighborhoods, but visitors usually stick to three on the city's Atlantic, or northern, edge: Isla Verde, Condado, and Old San Juan. (Another barrio, Santurce, isn't the most tourist-friendly, but it does have the central market and La Casita Blanca restaurant.) Taxis are always available, although the ride from Isla Verde to Old San Juan can cost $20, and you'll probably make the trip several times during your stay. Cars can be rented for as little as $35 a day, but traffic and parking can be a problem. Driving is about as easy -- or as stressful, depending on your point of view -- as in any large mainland city. Nearly everyone speaks English, and U.S. dollars are the currency.
on the natural side
Just an hour outside of San Juan, and I could breathe the difference. The air was fragrant with forest decay and a hint of rain -- no wonder, because I was in the Caribbean National Forest, or El Yunque. This part of the U.S. National Forest system gets 120 inches of rain a year. It is home to almost all that remains of Puerto Rico's vast rain forest.
Though it has many rivers, several peaks, and more than 250 species of trees, El Yunque was almost too easy to explore. Instead of the muddy paths found in most tropical forests, there are paved trails in some places, wooden steps above the rough spots, and a road winding up the mountain to lead lazy day-trippers like me from trailhead to trailhead without strenuous hiking. In a little less than three hours I made my way through steamy lowland rain forest, a palm forest spotted with clumps of ferns and mosses, and a magical dwarf forest, high in the mountains, where the trees are small, the epiphytic plants thick, and the clouds dense. The Taino Indians who once lived on the island believed that their gods passed the days here.
At one point I climbed to a lookout tower called Torre Britton. I found offerings of feathers and other objects from a recent ceremony of Santeria, the Afro-Caribbean religion practiced in Puerto Rico. I searched for blue-and-red flashes in the trees, but I never did see one of the endangered Puerto Rican parrots (only 32 of which remain in the forest).
Leaving El Yunque, I stopped at Luquillo Beach, white sand and calm water ringed with thousands of palms. Small, clean restaurants sold sandwiches, coco frío (a whole green coconut with a straw to suck out the water), and fritura (tacos, fritters, and other finger foods, filled with meat and deep-fried). A souvenir shop had pretty little jewelry boxes encrusted with seashells, and a stand rented beach chairs and umbrellas.
You could spend the afternoon at Luquillo, but I chose to visit the Cabezas de San Juan Nature Preserve (reservations required; 787/722-5882 weekdays, 787/860-2560 weekends; $5), a half-hour away in Fajardo. Its 316 acres contain a stunning variety of ecological zones, including mangrove swamps, coral reefs, dry forest, and phosphorescent lagoons. Going against my worst instincts, I refrained from pocketing a treasure on the coral-covered beach my tour visited, but was rewarded when our guide let me -- along with the kids -- hold a live sea urchin. A pleasant tram tour winds through the park and up to the 19th-century lighthouse with its commanding views -- the kind that make me think I could (and should) live here.
a sunset stroll
Descend Caleta de San Juan, a narrow street in the old city, until you hit the arched gate called La Puerta de San Juan. To the right is a rocky path that runs by the sea wall below El Morro. The trail, which takes about 30 minutes round-trip, offers a remarkable bit of solitude in the bustle of Old San Juan. You'll pass massive stonework put in place by the Spanish, and eroding 100-foot cliffs. Cruise liners and frigates ply the shipping channel, and fishermen cast lines from wave-drenched boulders. If you're inclined, bring some treats for the dozens of stray cats slithering around and napping on the sand.
the glowing stones
Whenever I walk in Old San Juan, my eyes are invariably drawn to the cobblestones the Spaniards used to pave the narrow lanes. These little oblong blocks shift mysteriously in tone throughout the day, from iridescent blue-black to gray and even to sky blue. Sometimes you'll come across one that has been decorated with a Puerto Rican flag sticker, a drawn-on marijuana leaf, a cross, or a set of lovers' initials carved in a heart. One morning I was squatting, examining some stones, when a middle-aged couple walked by.
"You like them?" asked the man, a dandy in white shorts and shirt and a straw fedora.
"They absorb the color of the night sky," said his companion, who was wearing an African-print gown. "If there's no moon the stones will wake up black. If it's a clear night the stones will open their eyes blue. By the end of the day they always fade to gray."
Before I knew it, the couple had disappeared. A quick stop at the tourist office cleared things up. Made in England using iron ore, the cobblestones were brought to the New World as ballast in ships and dumped at the harbor to make room for more valuable cargo. The iron gives the stones their color, which shifts depending on the heat, sun, and humidity. That night, in a dark bar in the old city, I discovered that I wasn't the only one captivated by them. The back wall was decorated with photographs of the stones. In the low light, the photographs glowed softly.
rum's the word
The promise of free rum is what draws most people to the Bacardi Rum Distillery (787/788-1500) across the bay in Cataño, but getting there is more than half the fun.
Hidden between the cruise ships in Old San Juan is a small ferry terminal where, for a buck, I bought a round-trip ticket to Cataño and climbed to the top deck. What followed was my second-most-pleasant afternoon in San Juan (the best was when I fell asleep after lunch in the shade of a palm tree, waves breaking a few yards away). I sat in the sun and watched the city and harbor drift by -- Isla de Cabras, Fort Cañuelo, the shark-infested waters off El Morro.
In Cataño, I caught a colectivo (a small bus) to the Bacardi plant. On a huge plot of perfectly manicured grass is a collection of Modernist buildings and a kitschy re-creation of a sugarcane plantation. (Funny, the guide didn't mention that slaves originally made all this possible, other than noting that the laborers "worked in exchange for food and housing.") The tour is a view of rum production as performed in a refrigerated, sterile plant. There's even a pop quiz on how to prepare tropical drinks -- and guess what, Bacardi's in all of them. But the rum flowed freely in cocktails and in the special spiked limonada, with no last call in sight. I caught a colectivo back to the ferry before things got out of hand.
where to eat
Some of the best food in San Juan is found at restaurants that fuse the flavors of Puerto Rico -- an Afro-Caribbean blend of the freshest seafood, fruits, beans, and spices -- with European styles. But there are also plenty of fine restaurants that have no hint of the islands.
Parrot Club 363 Calle La Fortaleza, Old San Juan; 787/725-7370; dinner for two $75. Navigate through the bar -- where Hollywood stars drink martinis with local glitterati, and everyone is tan, well dressed, and practiced in the air kiss -- and take a seat on the back terrace. Here, under the night sky -- where the stars twinkle above, not on the barstools -- chef Roberto Trevino serves an astonishing array of Euribbean foods from a menu written in Spanglish: tamarindo-glazed baby back ribs, risotto con chicharrones del país, Nuestra Famosa blackened tuna.
Il Perugino 105 Calle Cristo, Old San Juan; 787/722-5481; dinner for two $140. Chef and owner Franco Seccarelli has given a Roman ambiance to the colonial building, with murals, plush fabrics, and gilded statues. All the better to show off his traditional Italian dishes: carpaccio classico, pennette all'arrabbiata, scaloppine alla pizzaiola. Quiet and discreet, this is the ideal place for lovers seeking an escape, and for others in the mood for tiramisù.
Urdin 1105 Avda. Magdalena, Condado; 787/724-0420; dinner for two $70. Stylish, young Julian Gil meets you at the door of his distinctly modern restaurant. The menu is sophisticated but not fussy, in keeping with the restaurant's minimalist approach. A pleasant staff serves squid with garlic and cilantro, seafood paella, and enormous steaks. Wear Prada, and arrive late.
El Picoteo Hotel El Convento, 100 Calle Cristo, Old San Juan; 787/643-1597; dinner for two $40. Anywhere else, the setting -- a terrace overlooking a courtyard, flamenco music in the background, a clear view of the sky above -- would overshadow the food. But the tapas are as delightful as the still-life of acid-colored tropical fruits on the bar's pomegranate wall. Start with the shockingly refreshing green salad with hearts of palm and a crisp mustard dressing, and follow it with the bacalao (salted codfish), a difficult dish done well here.
La Casita Blanca 351 Calle Tapia, Santurce; 787/726-5501; dinner for two $25. In a working-class neighborhood with traditional wooden Caribbean houses, the charming and slightly run-down Casita Blanca makes some of the city's best comida criolla. Sit in the courtyard, decorated by an eccentric with a passion for the country life (at some tables, green fronds sprout from coconut shells, and along the wall, roosters in one cage crow at white doves in another). Shrimp a la criolla is sweet with tomatoes and garlic. Spice it up with pique, the hot peppers soaking in vinegar found in bottles on every table. After your last sip of limonada, the friendly waiter will no doubt convince you that a dish of rice pudding is in order, topped off with a chichaito (anise and rum).
La Bombonera 259 Calle San Francisco, Old San Juan; 787/722-0658; lunch for two $20. The old-fashioned soda-shop atmosphere is as much a draw as the food, a straightforward mix of sandwiches, shakes from an old Hamilton Beach blender, and Puerto Rican specialties such as seafood stew. Don't expect sterling (or even prompt) service, but do enjoy the café con leche and pumpkin pudding at the end of your meal.
Kiosko 4 Estaciones Plaza de Armas, Old San Juan; lunch for two $8. A snack stand smack in the middle of a lively plaza where, in the early evening, lovers kiss on the edge of a fountain, kids play, and old men sneak slugs from their vest-pocket pints. The food is basic -- coffee, sodas, sweets, sandwiches -- but the people-watching is spectacular, and it's open 24 hours.
The resort hotels of Isla Verde are great for extravagant shows and gambling, and discos like Egipto can keep you dancing to hits for hours, but the best night out consists of weaving through the mix of high-end and low-life bars of Old San Juan, drinking and dancing through several cultures.
Like the locals, I began my night late, around 10, meeting friends at Carli Café Concierto (206 Calle Tetuán, Plazoleta Rafael Carrión; 787/725-4927), a pleasant place with a terrace that's ideal for drinking margaritas and watching the parade. Besides the sun-fried cruise-boat tourists, elegant Puerto Rican couples, skateboarders, and strolling families, the street crowd this night included a thirtyish woman in a long pleated dress and heels. Bannered across the soft, café con leche skin between her shoulder blades was an elaborate tattoo: PERDÓNAME MADRE MÍA ("Forgive me, Mother"), the sad calligraphy read. She turned, saw me staring, and smiled lightly. There were tattooed teardrops on her cheek.
My friends and I made our way up the hill to Hijos de Borinquén (Calle San José at Calle San Sebastián; no phone). The checkered floor, posters of palm trees and girls in bikinis, and live music from an XXXL guitarist and a petite bongo player made me think I'd stumbled into a relic of the old city in the days before it was restored. Medalla beer, the excellent local brew, is the drink of choice. Leaving, I noticed a ruin of a building, the doorway painted with a replica of the flag used by Puerto Ricans in the 19th century. The political display was a quiet reminder of the conflict between Puerto Ricans who want to secede from the United States and those who don't. (A December referendum ended with a majority of voters choosing the status quo).
The next stop was Aquí Se Puede (50 Calle San Justo; 787/724-4448), where the dreadlocked bartender grinned as she served up a rum and tonic, and the stools were occupied by casually cool people, including a beautiful woman with short hair, yellow lenses in her sunglasses, white jeans, a muscle shirt, and colorful tattoos. Other upscale hippies and fashionistas lounged at tables, and just when it seemed that I'd wandered into a photo shoot, a woman in a white muumuu started dancing to the Cuban salsa music with a man in a wheelchair. Others joined them, and soon the room was filled with twirling dancers, completely unselfconscious and given over to the music, not a poseur among them.
Wanting live rhythms, my friends led me to nearby Rumba (152 Calle San Sebastián; 787/725-4407), where the crowd spilled out onto the cobblestones, hoping to cool off during a break in the music. Long and narrow, with 20-foot-high ceilings, Rumba was packed with overweight businessmen, sleek young Rastafarians, and every permutation in between. The rumba was acoustic and intense, and even amateurs were welcome. A word of advice: Keep your knees bent and move from the hips.
At about four in the morning, I stopped in at El Farolito (277 Calle Sol; no phone), a tiny shot-and-beer bar decorated with oil paintings of nefarious, drunken people. Although a quick survey of the patrons indicated they'd make apt subjects for the house artist, El Farolito felt safe enough. Try a coco frío with rum. It's open from noon until "whenever," says the bartender.
Entering the courtyard of my hotel, I heard women singing softly -- a group of New Caledonians and Australian Aborigines in town for a United Nations conference. I fell asleep to their sweet sounds just as the sun was rising. A typical night in Old San Juan.
on the radio
San Juan is famous throughout the Caribbean and Latin America for producing an unusual number of music stars. Here's who's hot now around the city.
• Fiel a la Vega These down-to-earth guys bang out a modern reprise of trova, the heartfelt rock music that was so popular in the islands in the seventies. The group is in the vanguard of the resurgent "rock en español" movement sweeping Puerto Rico.
• Olga Tañon An island diva who brews a mix of merengue -- the hyperactive Latin dance music that even klutzes can move to -- and schlocky, sentimental Spanish pop. Somehow, it seduces.
• Ricky Martin Lush Latin pop in a surprisingly original mix of styles, ranging from the accordion lilts of cumbia to the trance-inducing rhythms of Cuba. Martin is a sex symbol all over Latin America, but his music has unexpected depth.
• Gilberto Santa Rosa Classic salsa -- complete with staccato horns, careening piano, and a singer who knows about love lost and gained.
• Marc Anthony and La India Two of the leading purveyors of modern salsa, which mixes slick production, urban edginess, and old-fashioned rhythms. These are by far the two most popular voices on the island -- even though they live in Nueva York.
• Luis Rojas A satisfying fusion of Caribbean and Latin music with a rock-and-roll heart. Rojas is often called the Puerto Rican Bob Dylan.
if you like piña colada...
No visit to San Juan is complete until you've sipped at least one tropical drink, and you've passed a brief meditative moment in front of 104 Calle La Fortaleza, in Old San Juan. The bronze plaque reads: "The house where in 1963 the piña colada was created by Don Ramón Portas Mingot." Too bad he didn't get royalties.
There's no shortage of shopping, whether you're on the prowl for a tropical bird (they're sold from the back of a pickup near the Coast Guard base) or a tennis sweater (try the Polo Ralph Lauren outlet in Old San Juan). Here's a selection of some of the most interesting places to browse.
DMR (Designs & Museum Reproductions) La Cochera Bldg., 204 Calle Luna, Old San Juan; 787/722-4181. A cool, calm spot on a mad, muggy day, DMR sells handmade mahogany veranda chairs in children's sizes, colonial-style paintings, and reproductions of Caribbean plantation furniture.
Jah Rastafari 366 Calle San Francisco; 787/725-5432. Imagine you're in Jamaica as you browse through everything from T-shirts silk-screened with portraits of Bob Marley to red, green, and yellow driving gloves. Reggae blares as Rastas compete with punk skateboarders for the newest CD's.
Olé 105 Calle Fortaleza, Old San Juan; 787/724-2445. Go for the hand-carved trinkets, colonial paintings, antique santos (carved images of saints), and curiosidades.
Plaza del Mercado Calle Capitol at Calle Dos Hermanos, Santurce; 787/723-8022. A pretty, old-style Caribbean building housing what is perhaps the most serene central market in all of Latin America. The botanicas sell medicinal herbs, Santeria offerings, bay rum, candles, and patchouli roots, which are used in "religious ceremonies and to kill cockroaches." There's even a "spiritual" floor cleaner. Pause for a mango-banana shake along with a plate of roast pork at one of the simple restaurants.
El Alcázar 103 Calle San José, Old San Juan; 787/723-1229. Entering any of the many rooms here is like discovering a forgotten attic in a Newport mansion, filled with treasures from trips around the world. The selection might include a 19th-century Tibetan incense burner or a carved-wood Christ figure.
Read T+L’s guide to Puerto Rico for more destination ideas.