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42 miles S of Fort Myers; 106 miles W of Miami; 185 miles S of Tampa

Ah, sleepy, swanky Naples. This is a place that may have defined the meaning of R & R, since there's not much to do here besides linger on the beach, play golf, and dream. Naples is also easily Southwest Florida's most sophisticated city. But while Naples has its requisite waterfront mansions, country-club fairways, and a thoroughfare of pricey boutiques and restaurants, it's not nearly as upper-crust as, say, Palm Beach. Although the people are indeed Ralph Lauren types, heavy on the starch, the snobbery factor and upper-tax-bracket lockjaw are conspicuously absent here -- unlike the east coast of Florida, which is just as moneyed, but nowhere near as friendly or laid-back.

The long-bearded man dressed in ratty shorts and a Hawaiian T-shirt might just walk past you and hop into a Bentley or zillion-dollar yacht. Therein lies the beauty of Naples. People are wealthy here, but have no need to flaunt it -- what they do flaunt are St. Tropez tans and a general joie de vivre. Leave the kids at home -- even though there's a zoo here, it's not a place where the little ones will have fun. Naples is a romantic spot for couples; it's not a swinging singles scene whatsoever. The median age in Naples can't be much lower than 45, but Naples itself isn't a spring chicken, either.

Naples was born in 1886, when a group of 12 Kentuckians and Ohioans bought 8,700 acres fronted by a gorgeous beach, laid out a town, and started selling lots. They built a pier and the 16-room Naples Hotel, whose first guest was President Grover Cleveland's sister, Rose. She and other notables soon built a line of beach homes known as "Millionaires' Row." Today the area is known as Olde Naples and is protected by its modern residents. Despite a building boom that expanded the city, the original settlement still retains the air of that time more than a century ago.

Although high-rise buildings now line the beaches north of the old town, the newer sections of Naples still have their charm, thanks to Ohio manufacturer Henry B. Watkins, Sr. In 1946, Watkins and his partners bought the old hotel and all the town's undeveloped land, and laid out the Naples Plan, which created the wealthy but environmentally conscious city you see today.

About 4 miles north of Olde Naples, Vanderbilt Beach has a more traditional beach-resort character than the historic district. Lined with high-rise hotels and condominiums, the main beach here sits like an island of development between two preserved areas: Delnor-Wiggins Pass State Park to the north, and a county reserve fronting the expensive Pelican Bay golf course community to the south.