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Insider: Orlando Confidential

Florida chic means more than Miami these days. Orlando (yes, Orlando) has become a tantalizing, luxury-minded hallucination, "themed" with movie-set precision. And fashion folk like Helmut Lang, Calvin Klein, and Jill Stuart have been rushing to Jacksonville, looking for inspiration. Surprised? You won't be when you see what they've found. Throw in deserted beaches, sophisticated new menus, cutting-edge entertainment technology, and old-school resort-era charm, and voilà — you have America's most popular vacation destinations, but on your own stylish terms.

ORLANDO HOTELS + RESTAURANTS

The Contemporary Resort in Walt Disney World (at the Magic Kingdom; 407/934-7639; doubles from $295) is to Orlando what the Desert Inn or Caesars is to Vegas, an emblem of the city's iconic promise. Arrive by monorail, which whirs quietly through the cavernous lobby. On the 15th floor, have a glass of Krug and a plate of toro at the bar of Orlando's hippest restaurant, the California Grill (407/939-3463; dinner for two $70). You'll love the view of Cinderella Castle, white against that squid-ink sky — not to mention the 100 wines by the glass, no-attitude vibe, and nightly fireworks over the Magic Kingdom. Even the fresh-scrubbed tourists get awfully louche here. • The most luxurious spot in town? Universal's Portofino Bay Hotel (5601 Universal Blvd.; 407/503-1000; doubles from $245): studio-sized bathrooms, sumptuous beds, and punishingly seductive expanses of plazas, pools, and lounges. Re-create tense moments from The Talented Mr. Ripley, pretending not to recognize your friends as you walk past, footsteps echoing on the harbor piazza. Buy yourself a drink in the American Bar, a mellow waterfront lounge that NBA stars and movie moguls have made their own. Dine on haute Italian in the hushed Delfino Riviera (407/503-1000; dinner for two $66). • At Fish Bones (6707 Sand Lake Rd.; 407/352-0135; dinner for two $60), tourists mingle with local golfers and tennis hotties in a nautically themed patio atmosphere, with cocktail-hour lighting. • Go to Emeril's Orlando (Universal CityWalk; 407/224-2424; dinner for two $130) for the tasting menu: crawfish-and-cornbread-stuffed quail with venison prosciutto, seared ahi with watercress, cashew crème brûlée. Despite the theme-extreme CityWalk landscape outside the windows, a genuine calm prevails in the second-floor dining room, making this outpost of the "Bam!" empire more relaxing than any of Emeril's three New Orleans hot spots.

NIGHTTIME

Barhop the Disney hotels. Really. For a maximum mind-bender, be sure to wallow in the Kennebunkport vibe of the Grand Floridian and then rush to the nearby Wilderness Lodge, where they take Yosemite very seriously, right down to the roaring fire (perfect for those swampy nights). If you're looking to shake your groove thing, the dance-mecca Tabu (46 N. Orange Ave.; 407/648-8363) and the mostly gay Parliament House (410 N. Orange Blossom Trail; 407/425-7571) offer a wilder club scene. For stopless topless, take your pick of the showgirl bars on Orange Blossom Trail in downtown Orlando.

ISLAND LIFE

The newest theme park at Universal Orlando, Islands of Adventure (1000 Universal Studios Plaza; 407/363-8000; $46 for adults), is a $2.7 billion miracle of whimsical design. The scale? Larger than life. Rides such as the Amazing Adventures of Spiderman and Popeye & Bluto's Bilge-Rat Barges are gee-whiz multimedia knockouts — while Seuss Landing is a giggling, riotous Pop explosion, with a genuine Green Eggs and Ham Restaurant and a genuine Sneetch Beach. If you stay at the Portofino Bay Hotel, you get front-of-the-line access until noon. • At SeaWorld's upscale water park, Discovery Cove (7007 SeaWorld Dr.; 877/434-7268; $179 adult day pass and seven-day admission to SeaWorld), you can swim with dolphins, snorkel with stingrays, or bob along the Lazy River, through waterfalls, and into a tropical aviary where exotic birds eat from your hand and sweet puppy-sized deer cuddle against your shins. After lunch at the patio cafeteria, nap on lounge chairs scattered across the enormous, nearly bug-free beach. • Wet 'n Wild water park (6200 International Dr.; 407/351-3200; $29) is like a Stella McCartney T-shirt come to jubilant life. Join a group of very Abercrombie & Fitch dudes at the splash-pool bottom of Der Stuka, the park's steepest ride, to watch buff girls and boys lose their bathing suit tops and bottoms in the whooshing descent. On your way out of the park, order custom airbrushed T-shirts from Monsoon Mike; he's got an encyclopedic catalogue of old-school designs at nice prices. • Swimming at Disney's Typhoon Lagoon (Walt Disney World Resort; 407/560-4141; $29) is like paddling around in a Sigmund and the Sea Monster set: raft slides, bareback slides, and hidden beaches. An enormous wave pool produces Perfect Storm-worthy breakers.

DAY TRIP

Go west of Orlando, 106 miles, to Clearwater's tranquil shores. Or go east 60 miles to the pristine Canaveral National Seashore. Drive 45 minutes south to shop for citrus fruits and taste their sublime juices at Hale Groves (9255 Hwy. 1, Wabasso; 800/289-4253). Halfway between Orlando and Jacksonville, pull off the road to claim your stretch of the perfect red-sand beaches at Ormond by-the-Sea.

SHOPPING

Strut through Orlando's version of Manhattan's East Village, a three-block slice of North Orange Avenue lined with cafés and consignment shops — make sure to stop at Flo's Attic (1800 N. Orange Ave.; 407/895-1800). Browse for fashion's up-and-comers on the racks at Tuni's (301 Park Ave. S.; 407/628-1609), an oasis of actual chic in upscale Winter Park. Or bargain-shop at Orlando Premium Outlets, filled with Armani, Burberry, Versace, and Barneys New York (8200 Vineland Ave.; 407/238-7787).

FASHIONABLE JACKSONVILLE

With its prairie-style architecture and small-town friendliness, Jacksonville would seem an unlikely place for the fashion set. Yet thanks to one Florida designer who died last year at 88, leaving behind 100,000 pairs of his signature shoes, it couldn't be much hotter. "Joseph La Rose shoes scream Florida so loudly they actually transcend it," says Tiffany Dubin, author of Vintage Style. Currently, the Florida shoemaker's confections, beloved by Joan Crawford and Jackie Kennedy, are available only at Manhattan's hipper-than-thou Cherry boutique (185 Orchard St.; 212/358-7131). Serious shoppers, however, can make an appointment with Cherry's owners to tour the Jacksonville warehouse, which still houses 50,000 pairs, and take in the town's sights. Near the original La Rose boutique, on Hemming Plaza, is the Jacksonville Museum of Modern Art (333 N. Laura St.; 904/366-3911), whose collection ranges from Picasso to Robert Longo. (An exhibition of La Rose shoes is in the works.) From the plaza, cruise across the Blue Bridge over the St. Johns River, which divides the city. For dinner, follow the fashion set's lead: French chic at Bistro Aix (1440 San Marco Blvd.; 904/398-1949; dinner for two $60) and taxidermy-casual at Clark's Fish Camp (12903 Hood Landing Rd.; 904/268-3474; dinner for two $40). Sleep off your meal at the Lodge at Ponte Vedra Beach (607 Ponte Vedra Blvd., Ponte Vedra Beach; 904/273-9500; doubles from $175), in Jacksonville's toniest beach suburb.

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