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.
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.
