42 miles S of Fort Myers, 106 miles W of Miami, 185 miles S of Tampa
Ah, sleepy, swanky Naples. A place that may have defined the meaning of R & R, considering the fact that there's not much to do here besides linger on the beach, play golf, and dream that this isn't a vacation but a way of life. Naples is also easily Southwest Florida's most sophisticated city. But while Naples has its requisite waterfront mansions, sprawling country-club fairways, and a thoroughfare of pricey boutiques and restaurants, it's not nearly as upper-crust as, say, Palm Beach or Beverly Hills. Although the people are indeed very 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.
Don't even think of thumbing your nose at the long-bearded man dressed in ratty shorts and a Hawaiian T-shirt until you make sure he doesn't 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. Your relaxation will be disturbed when little Johnny and Jane start tugging at your shirt whining of boredom. Naples is a romantic spot for couples; it's not a swinging singles scene whatsoever. In fact, this is the kind of city where young singles need to try out for reality shows in order to find a mate. But you never know if the Mr. or Ms. Howell sitting at the bar is recently divorced and looking for a companion with whom to share their wealth. 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 carefully protected by its modern residents. Despite a building boom that expanded the city, the original settlement still retains the air of that time 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 very 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.
