I remember the first time I saw Longboat Key. It was 1967, and my family had just moved to Florida. Dad and Mom crammed us four kids in the back of our Pontiac and took us on a Sunday drive down Longboat Key. Except for the short finger avenues of Country Club Shores, where small, cement-block ranch houses were being constructed, the entire southern half of the island was as empty as it had been during World War II, when the Air Force used it as a target range. I'll never forget Dad's reaction: 'Who the hell would want to live out here in the middle of nowhere?'"

That, of course, was just five years before the Arvida Corporation (now St. Joe Towns and Communities) descended on the isolated island community and tipped everything upside down. Between 1973, when it built Seaplace, its first Gulf-front condominium community, and 1994, when it completed the bayfront Grand Bay, Arvida created a genteel Northerners' vision of paradise, lining Gulf of Mexico Drive with pink oleanders and meandering golf courses and building exclusive gated neighborhoods on either side. Retirees from the Midwest and Toronto flocked to the new developments. Many spent much of the winter here, golfing, walking or biking the wide, paved path along Gulf of Mexico Drive, frequently hosting visiting children and grandchildren, and enjoying the island's beaches, family-owned restaurants and shops and the amenities of nearby Sarasota.

For centuries Longboat Key was a camping ground for native Indians; from the late 1880s to the great hurricane of 1921 it was an agricultural center that produced avocados, papaya and tomatoes. By the 1950s, says David Miller, second-generation owner of Cannons Marina and Cannons-by-the-Sea vacation cottages, there were a few more people but the key was still mainly "a place where rabbits, raccoons and rattlesnakes lived." Today, this island west of Sarasota is a 12-mile stretch of beach-to-bay manicured resort living, with multimillion-dollar condominiums and mansions set amid golf courses and tennis clubs and gated communities of handsome single-family homes. It also has a few fashionable boutiques, a handful of restaurants and two big resorts-The Colony Beach and Tennis Club, one of the top-rated tennis resorts in the country, and the Resort at Longboat Key Club. Both attract wealthy visitors, including a smattering of celebrities.

Along with the ritzy resorts, Longboat is home to some friendly mom-and-pop beach hideaways, an anomalous "village" at the north end where concrete-block ranch homes and a few last wooden cottages like Cannons-by-the-Sea from a less glamorous era remain. Mid-key stand two mobile home parks, Gulfshore and Twin Shores. The parks have 298 mobile homes between them; the last to change hands at Gulfshore sold for $179,500.

Longboat has a year-round population of nearly 8,000, a peak tourist season population of 23,500 and a reputation for being one of America's most affluent resort communities. In 1999, Money magazine named it "one of America's five wealthiest zip codes."

Palm Beach is flashier, and Hobe Sound is more the woody-station-wagon kind of old money. Longboat has bits and pieces of both those places and of Naples and Fisher's Island, too. But Longboat's combination of Gulf and golf has drawn many of the nation's top corporate executives-men (mostly) of a certain age whose hard work and bright ideas took them up their corporate ladders and who are ready for active retirement. "At a tennis scramble, I remember, I introduced myself to my partner and asked him what he did," says former mayor Jim Brown. "He told me, 'I was in radio with ABC.' I said, 'Oh, really. What did you do at ABC?' He told me, 'I was chairman of the board.'"

Brown, a former newspaperman, retired to Longboat Key from Michigan in 1976, was elected town commissioner in 1989 and served four terms as mayor until his retirement from politics in 1994. Today, he writes a weekly column about Longboat Key for the Sarasota Herald-Tribune.

He says that although the island may feel impenetrable to a visitor driving north along Gulf of Mexico Drive, "It's not a closed community. New people are welcomed here. People run for town commission who have lived here three years. People do get involved."

And Brown says that although residents may be seasonal, they're not afraid to tackle their town's problems. "We're on the third round of beach renourishment, we built a new town hall, fire stations, a new public works department. We were probably the first community in Southwest Florida to vote for a bicycle path, and we voted to tax ourselves to build it."