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."

The different social scenes swirl around golf and tennis at the Longboat Key Club, or classes and lectures at the art and education centers, or the churches and the one synagogue. The biggest social event of the year is the St. Jude's luncheon in November; it's become a Welcome Back gala, and 800 to 1,000 residents turn out. Last year, it raised almost $30,000 for St. Jude Hospital in Memphis.

George Rauch, who moved to a wooded, bayfront property on the north end of the key with his wife, Sally, 31 years ago, says Longboat has been an idyllic place to live and to raise their three children. He remembers when there were only two high-rise condominiums along the Gulf, and an evening's entertainment would be walking across to the beach to build a bonfire and cook hot dogs and hamburgers with friends. Today's Longboat may be richer and more sophisticated, he says, but it's still an easygoing place where plenty of old-timers know each other and people are more "down to earth" and less "status-conscious" than in resort enclaves such as Palm Beach.

"Oh, my God, it's fabulous, we have everything out here," agrees gregarious Murf Klauber, who just celebrated his 35th anniversary as owner of The Colony Beach and Tennis Resort. "My new car is a year old and I have 1,100 miles on it."

Janet Walter, 33, marketing director at the Flanzer Jewish Community Center, who moved from the mainland to the north end of the key with her husband, Steve, three years ago, says life on Longboat is "awesome." They bought a home on a quiet street with canals on either side, where many of their neighbors are also young couples with children; and though they both work in Sarasota, Walter says the drive, with its expansive views of the Gulf, is so beautiful they don't mind the commute. Weekends, they kayak across the canal to visit neighbors, cruise around in their boat or meet friends for dinner at Mar Vista, a casual bayfront restaurant, or Pattigeorge's, a trendy mid-key place.

"I've never felt isolated," says Walter. When she was pregnant with her second daughter, she ran on the bike path along Gulf of Mexico Drive right up to her last week. One day in the Publix at Avenue of the Flowers, two Longboat policemen told her, "We know you! We've been watching to make sure you don't fall down."

But skyrocketing property values and a fundamental change in demographics are changing Longboat Key once again. A bastion of quiet affluence and Midwestern conservatism mixed with a sizeable contingent of Canadians in the '70s and early '80s, the population has steadily become artier, more urbane, more liberal and more drawn from the New York and the Northeast. Now it's also becoming richer-much richer, say island residents.

"We're seeing a lot of wealthy newcomers," Rauch says. "They come in on corporate jets-Dolphin Aviation is stacked with them." And as property values have risen, the comfortably well-off retirees who could once afford a nice home in Country Club Shores or the artists who could buy a funky little cottage in the Village can no longer pay the price of admission. A nondescript home in the Village now sells for more than $400,000; and Walter, who notes that she and her husband bought their home right before prices began to shoot up, says many young couples in their neighborhood do not work-presumably, they are "trust-fund babies," she says, with private incomes.

Along with soaring home prices have come soaring property taxes. Rauch says that many part-time residents (who do not qualify for Florida's homestead exemption tax break and the additional three-percent-per-year limit on property tax increases) can't pay their ever-escalating tax bills. "They're selling their property and moving to North Carolina," he says. How high are property taxes? Rauch has a friend who recently bought a Gulf-front Longboat home. "He's paying $76,000 a year [in property taxes] for a house on a 100-foot lot," he says.

Annette Rogers swings her shiny white Mercedes through the gates of the Longboat Key Club and turns north along Longboat Club Road. "We call this the Longboat Riviera," she says, gesturing toward the pearl-hued high-rise condominiums and $10-million-plus waterfront estates that extend north of the Resort at Longboat Key Club. ("Houses," she shrugs. "They look like hotels.") She points out L'Ambiance, where philanthropist Bea Friedman's penthouse apartment was snapped up for $5.8 million the day it went on the market last year; the Pierre; the Sanctuary; Longboat Key Towers, the original high-rise, where Gulf and bay view units sold for $50,000 in the 1970s, $450,000 six or seven years ago, and $750,000 today; and Regent Place, where the ninth-floor apartment she sold to a friend for $900,000 nine years ago recently sold for $3 million.

What's happened to Country Club Shores is even more "unbelievable," Rogers says. "The most nondescript house [on Gulf of Mexico Drive] that was worth $50,000 in the 1970s is selling for $500,000 to $800,000; one went for $2 million. And the end lots on the bay-$4 to $5 million."

Rogers, who celebrated her 30th year of selling Longboat Key real estate in 2004, discovered the island in the 1960s as a vacationer at The Colony, "back when it was cottages with little screened-in porches, when Herb Field [an early island developer whose Buccaneer Inn on Dream Island Road was beloved by children, who could pick a prize from an overflowing treasure chest when they finished their meal] owned it," she remembers. A warm and energetic woman, she's one of Michael Saunders & Company's top producers, a member of an informal club of realtors who sold more than $30 million worth of Longboat real estate in 2003. ("But don't print that," she says. "It was much, much more.")

"In the old days, it was mostly Midwestern and only retirees," Rogers remembers. "Now a lot of younger people are coming in-young retirees and even people with children. It's a lot more interesting." Rogers stops to take a call from a Baltimore client, a businessman with a young family who plans to fly in the next morning and spend the day previewing potential second homes. Rogers' only dilemma: He wants something in the $700,000 range, and she's only found 11 listings on the island she can show him.

In the mid-1920s, John Ringling had big plans for bringing tourism to Longboat. He spent a fortune building a Ritz-Carlton on the island's southern tip, where the Chart House now stands. The Florida real estate bust and stock market crash of 1929, however, put an end to his dreams; the half-finished shell deteriorated for decades and was finally demolished in 1964.

Today, the island's tourism industry faces new adversity in the razing of hotel properties, large and small, to make way for high-end condominiums.

Shop and restaurant owners are nervously eyeing the closure last year of the 146-room Holiday Inn and the 50-room Silver Beach Resort, both on the Manatee County side of Longboat. The smaller, six-unit Starfish Motel also sold, but it remains open through the season; demolition is scheduled for this spring. The 25-room Holiday Beach resort was sold, but the new owners are denying rumors that it's coming down. (A look at the sale price explains why hotel owners might decide to sell out: The mom-and-pop resort was purchased in 1970 for $700,000; its owners sold it last July for $11.8 million.) And last fall, rumors swirled that the 14-unit Sea Bird Beach Resort would imminently close.

"We're definitely concerned," says Susan Estler, marketing director for the Bradenton Area Convention and Visitors Bureau. "Over the course of time, [the loss of these hotels] brings less people to the area, and that makes our job harder to promote the properties that are left." Let's face it, she says, the million-dollar-plus condos replacing these hotels "won't go into the rental pool."

Virginia Haley, executive director of the Sarasota Convention and Visitors Bureau, is also worried. "When you lose the hotel rooms, it's harder for places like restaurants and shops to stay open. And staying in a hotel is the most common way people are introduced to the area," she says. "Then the next time they come they say, 'Oh, we want to stay longer,' or 'we're maybe interested in relocating.'"

Historically, Longboat Key properties have drawn a large number of tourists to the area, accounting for about 15 percent of Sarasota County's bed tax, says Haley. "Remember that Longboat is split between the two counties," she says. "For us, the Longboat market has been the Resort at Longboat Key Club, the Colony, and the one- to six-month condo rentals. In Manatee County, it was the Holiday Inn and Hilton, and a lot of mom-and-pops."

Regardless of what side of the county line they choose, "the Longboat visitor is the most-wanted visitor," says Haley. "They spend a lot of money-and luxury travel is back big-time." They are older, more educated and wealthier than Sarasota County tourists as a whole, recent SCVB focus groups reveal. "They have the highest income of all our visitors in general," she says. How high? "We made a mistake and didn't ask high enough; we only asked to $125,000 or more, and the majority said more," Haley says. Interestingly, when the SCVB surveyed interests, Haley says, Longboat visitors were the only group who expressed an interest in attending the performing arts while on vacation.

Gail Loefgren, executive director of the Longboat Chamber of Commerce, is not panicking. The transformation of hotels to condos is not unique to Longboat, she says; "it's happening to all the oceanfronts all over the country." The chamber recently held a board retreat to strategize possible solutions. "You always have to be positive; we don't know, there may be things we can do to turn this to our advantage," she says.

Loefgren says chamber membership is holding steady at 534 member businesses, about 250 of which- primarily accommodations, retail and real estate-are located on Longboat. And last fall the chamber moved into a much larger, 4,700-square-foot building at the north end of the island, the former home of a bank branch that folded.

"About the time I retired from politics in 1994, development was essentially completed," says former mayor Brown. "Now the shift has changed to redevelopment." He points to another indicator of change: property valuations. Ten years ago, when Brown left office, the total was $1.7 billion. Now it's closer to $5 billion. "That's a lot of money," Brown says. "The last time I looked, we paid 11 or 12 percent of the total property tax in Sarasota County, and that's just half of the key."

Those taxes, point out Rauch, enrich Sarasota in many ways. "Schools are not much used by Longboat's population, but Longboat taxes support a very good school system that Sarasota otherwise could not afford," he says. "And money for the arts? Where does it come from? Longboat Key-we have a generous population of older people who donate to the arts."

But if Longboat's escalating wealth is good news for Sarasota, some worry that it will cost Longboat its long-established character.

"The bigger and more expensive the house," Brown says, "the less time people spend here. The people who own those mansions on the Longboat Riviera own three or four houses like that elsewhere, and probably spend a month here. The result is you're not changing the population, but you're decreasing the number of full- and half-year residents. When I was mayor, it was more of a mixed community. Ten percent of the registered voters lived in trailer parks. The price of the, I won't say lower-end, I'll say less expensive end, has skyrocketed."

Because of the growing part-part-time population and the replacement of the Holiday Inn and other hotels with ultra-luxury condominiums, Brown predicts, "Summers are just going to be empty here. Last summer the duplicate bridge club that meets Tuesdays at the rec center had difficulty having games because they couldn't find enough people."

That could also be the result of changing tastes, of course, as older, bridge-playing residents give way to a new generation with different interests. Brown concedes the guard is changing. "When we moved here we were in our 50s. The first party we went to at the country club, the band packed up at 9 o'clock. My wife said, 'My God, I stayed up later than this in junior high.' Now we leave at 8:30."

At the Longboat Education Center, in-season business has never been brisker, says executive director Susan Goldfarb. Some 2,500 islanders attended 150 classes at the education center between January and March last year. (It doesn't offer summer classes because of lack of students.) "It's not sleepy little Longboat Key with a few deep-pocket folks anymore. That's why we're doing better," says Goldfarb.

For all those who fear that Longboat will become a seasonal ghost town, a soulless enclave of glittering mega-mansions and multi-million-dollar condominiums used only occasionally during the year, there are others who insist it will remain a community, even if it's a community of a different sort. "People buy here and they love it and they make it their home," says Rogers. For example, she recently sold a five-bedroom home for $1.9 million in the bayou section of Bay Isles to a couple from Ohio in their late 40s or early 50s. They're home-schooling their two young boys, and intend to build a larger, more permanent home on a property they own along the Gulf. Such richer, younger residents will be the new Longboaters, Rogers and others predict, and if the island they live on has fewer businesses and motels, it will nevertheless be one of the most exclusive enclaves anywhere, bordered by miles of white beaches and within easy reach of the ever-more upscale services and diversions of Sarasota.

Real estate magnate Michael Saunders, who grew up on the island's north end where her uncle had a cottage in the late 1880s, agrees that in 10 years, Longboat Key residents will be "much younger, younger, younger. They will be living year-round and raising their children here, and that means a stronger sense of community." The growth to come, she forecasts, will be in rebuilding from mid-key northward, and to a lesser extent in Country Club Shores and Harbourside. "Hopefully," she says, "the craft-cottage feel of the north end of the key will remain."

And really, she adds, when it comes to Longboat Key, or much of Florida, for that matter, "There aren't many of us who can claim deep roots." Change is the nature of the place, especially in a retirement resort community-people pass away, taking their memories and sense of the place with them, and newcomers arrive and create their own memories and reality.

And to those who mourn the passing of the tranquil little island where thrifty, successful Midwestern retirees enjoyed their well-earned reward of winter sunshine and early dinners at the club, and the same family would return every spring to a rustic Gulf-front motel, there's this consolation. A more glittering Longboat Key will cast its glow on Sarasota, raising the city's national and international profile and affecting everything from real estate values and tax revenues to charitable giving and business opportunities. The Longboat magic will endure.

KEY FACTS

Year-round population over 7,600

Peak seasonal population (February-March 2003) 23,500

Ethnic composition 99.24 percent White

Households with children under 18: 3 percent

Average annual household income 1980: $32,800; 2002: $160,000

Percentage of households with income over $100,000 1990: 27 percent; 2006 (projected): 52 percent

Statistics courtesy 2000 U.S. Census, Town of Longboat Key and the economic forecasting firm of Fishkind & Associates, Inc.

WHO LIVES ON LONGBOAT?

Beyond Longboat Key's manicured lawns live celebrities, scions of industry, and offspring of some of America's oldest families. A sampling:

Marcella Hazan. Sometimes called the godmother of Italian cooking, Marcella and her husband, Victor, celebrated the debut of her sixth cookbook, Marcella Says, on the Today Show in October. Hazan earned a lifetime achievement award from the James Beard Association and a knighthood of the Star of Italian Solidarity from the Italian government, and is credited with, among many other culinary triumphs, introducing balsamic vinegar to America. The charming chef says she found many of the recipe ingredients for Marcella Says at the Publix at Avenue of the Flowers.

Joey Tanenbaum. One of Toronto's most well-known and prolific philanthropists, the former builder and his wife, Toby, have donated an estimated $200 million in artworks and money to museums and educational institutions there. The home of the Canadian Opera is known as the Joey and Toby Tanenbaum Opera Centre. Tanenbaum also funded the restoration of Toronto's first synagogue, in honor of his grandparents, who were members.

Mary Lou Whitney. The former Mrs. Cornelius Vanderbilt Whitney and now Mrs. John Hendrickson, she is the doyenne of Saratoga Springs; it's been said the thoroughbred racing season doesn't start there until she arrives. Whitney is owner of 2004 Belmont Stakes winner Birdstone, who upset Smarty Jones in his bid for the Triple Crown.

Bruce and Mary Ann Bozzi. He's the third-generation co-owner of the famed Palm Restaurant chain, which now has 25 upscale steakhouses in such major cities as Chicago, Atlanta, Boston and Washington, D.C., besides its flagship restaurant in New York.

Klaus Jacobs. Former chairman of the board and still major shareholder in Swiss-based Adecco S.A., which, with over 130,000 clients and 650,000 employees around the globe, is the world's largest employment company.

Aaron Cushman. The public relations legend is founder of CushmanAmberg Communications, Chicago's biggest p.r. agency. His new autobiography, A Passion for Living, dishes the long list of icons-from Harry Truman to the Three Stooges-whom he has counseled.

Leo O'Neill. Chief executive of Standard & Poor, who guided the expansion of the bond rating firm into 20 countries, passed away last April; his widow, Kip Bleakley O'Neill, is a legislature in Duchess County, N.Y.