Mention Naples, Florida, and images of ostentatious wealth quickly come to mind. On any given day, driving its residential streets requires dodging landscape company trailers for the hundreds whose buzzing equipment grooms banyan-lined, palm-studded green carpets of St. Augustine. Surely few places its size have more golf courses, gated “communities,” palatial homes, in-ground swimming pools, posh boutiques, and high-luxury cars (The town’s Ferrari Club is one of several local enthusiasts’ organizations). A trip down Fifth Avenue South conjures a vision that is one part Mediterranean seaside town and one part lifestyle center. It was not always so.

For much of the twentieth century, as American Tourism contributor Aaron Cowan of Slippery Rock University argues, Naples mixed downscale “old Florida” with upscale nods to Palm Beach. Perhaps nothing symbolized the enduring presence of old Florida more than Swamp Buggy Day. Created in 1949 by enthusiasts of swamp buggy racing (which involved the ultimate “sport utility vehicle, a balloon-tired amphibious craft), this civic celebration grew around the sport and included a swamp buggy parade down Fifth Avenue South.

Swamp Buggy Day Parade in the early 1950s. State Archives of Florida, Florida Memory.

As Naples built its reputation as an upper-class winter destination, Swamp Buggy Day evolved into Swamp Buggy Days. Drawing larger crowds each year as a result of national TV coverage on ABC’s Wide World of Sports in the 1950s, eventually the downtown parade clashed with the town’s efforts to make downtown streets more appealing to well-heeled snowbirds.  According to an article in 1962 in the St. Petersburg Times, officials responsible for the Swamp Buggy Days parade “decided that beauty should prevail over tradition and the line of parade moved off the Fifth Avenue South business area for fear the crowd, lining the avenue, would ruin or damage extensively the $15,000 worth of planting recently installed there.” The decision prompted a furor, with some arguing that the parade would not be the same if moved to another route. Ultimately a compromise was reached whereby the route would be shifted four blocks down Fifth Avenue South so as not to “endanger the ornate plantings to the west.”

Worth Avenue, Palm Beach, 1946. By the end of the twentieth century, Fifth Avenue South was converging aesthetically more and more with Palm Beach’s refined thoroughfare. State Archives of Florida, Florida Memory.

Eventually the parade shifted over to the Tamiami Trail (U.S. 41), a multilane highway that skirts “Old Naples” to the east, ending two blocks to the north of the city’s prettified main drag. Then last year the City of Naples, seeking to trim its budget, voted to stop sponsoring the annual event, turning over responsibility to the Collier County Sheriff’s Department. In a sense the parade, still highly popular, reflects changes all along Florida’s coastline, where tastes–and incomes–skew toward the high end while “old Florida” recedes ever farther inland. If U.S. 41 once divided the pricey from the affordable, in the last decade, as more and more tourists have made the destination home, the boundary has marched eastward to I-75 and beyond, propelling the market for affordable housing far away from the Gulf.

Naples straddles two worlds: Ferraris centered on Fifth Avenue South and swamp buggies at Florida Sports Park, home of the Swamp Buggy Races, at the dead end of Rattlesnake Hammock Road–and, for a day, parading U.S. 41. As a New York Times reporter noted several years ago (Robert Andrew Powell, “On Florida’s West Coast, A Would-Be Palm Beach,” New York Times, March 12, 2004, F1), one ambivalent buggy racer and air conditioner installer who turned to selling high-end real estate mourned the gradual eclipse of old Florida. For now, though, the swamp buggies roll on in Naples.

Tropical landscaping added to the refined appeal of Fifth Avenue South by the 1960s. State Archives of Florida, Florida Memory.