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.
The pier came first. Construction began in June 1888 — a six-hundred-foot freight-and-passenger dock that was, for years, the only practical way into town, with the post office itself sitting out on the pier after 1889. For decades Naples stayed a small, isolated winter colony reachable mainly by steamboat, supported by fishing and a little farming. Then in 1927 the Seaboard Air Line railroad arrived — the Orange Blossom Special pulling into the new Naples Depot on January 7 — and in 1928 the Tamiami Trail finally linked Naples to Miami and Tampa. The isolation that had defined the place was over.
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.
