The Gulf shore here was Calusa homeland for centuries before any of it carried a Kentucky accent — the people who fished these waters and met the first Spanish ships off this coast in 1513; Seminole people followed in the early 1800s. The town itself begins in the autumn of 1886, when the Naples Town Improvement Company — organized by Walter N. Haldeman, publisher of the Louisville Courier-Journal, and his partner John Stuart Williams, a former Confederate general and U.S. senator from Kentucky — bought 3,712 acres between the Gulf of Mexico and Naples Bay for $11,136. They named the place after the Bay of Naples in Italy and marketed it as the "Bay of Naples of America," a winter retreat for wealthy Northern families.
A few landmarks carry the early colony into the present. Historic Palm Cottage, built in 1895 of tabby mortar — a mix of lime, crushed shell, and beach sand — is the oldest house in Naples and today the home of the Naples Historical Society. Out past the edge of town, the gladesman country gave Naples its other identity: the Swamp Buggy Races, first run formally on November 12, 1949, when home-built marsh machines tore through the mud at the start of a tradition that still runs today. And after mid-century growth nearly buried the old main street, the 1990s brought a celebrated revival of Fifth Avenue South — a redesign that turned the historic town-to-pier street into one of the country's most admired walkable downtowns.
Why People Visit Naples Florida
Most people come to Naples for the beaches, the golf, and the Gulf sunsets — but the city rewards anyone who looks for the older layer underneath: a winter colony planted in 1886 and named for an Italian bay, a pier rebuilt through more than a century of hurricanes, and a frontier-grit swamp-buggy tradition at the edge of the Everglades. It's bright, warm, and welcoming, with its real history sitting quietly alongside the resort polish.
