Naples Florida — Retro Vintage History

Before the golf courses and the galleries, there was a newspaperman and a pier. In 1886 a Louisville newspaper publisher bought 3,712 acres of Gulf-edge wilderness, named it after a bay in Italy, and sold it to Northern families as paradise. In 1888 he built a pier into the Gulf of Mexico — a dock that storms have taken down and the town has rebuilt time and again. That's the Old-Florida story underneath the Paradise Coast: the winter colony, the pier, the swamp buggy, and Fifth Avenue South — and this page tells it.

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.

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.

What's with the Kentucky in Naples? Look hard at the founding and it's Bluegrass all the way down. The man who started it was a Louisville newspaper publisher; his partner was a Kentucky senator. The winter families they sold to came down from Kentucky and Ohio — and they named this stretch of Gulf wilderness not after anywhere in Florida but after a bay in Italy, then talked Northerners into believing it. A swamp-edge rechristened as a Mediterranean, sold out of Louisville. The Italian name stuck, the pier went up in 1888, and the Kentucky winter-colony idea quietly became the Paradise Coast.

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.

Our Naples logo carries Florida's alligator over "1845," the year of statehood and the shared emblem of every Merlin Classics Florida place. The alligator is the Everglades in shorthand — and Naples sits right at the gateway to the Everglades, the Ten Thousand Islands, and Big Cypress, where the gladesman frontier meets the Gulf-coast resort. Printed black-and-white with the worn look of an old crate label or a piece of marsh-camp signage, it reads as Old Florida. What makes this one Naples is the place behind it: the 1886 winter colony, the 1888 pier, the swamp buggy, and the home by the Gulf.

Today Naples is one of the most polished resort cities on the Gulf — the paradise its founders advertised — but underneath the galleries and the golf is a genuine Old-Florida story: a winter colony a Louisville newspaperman named after an Italian bay, a pier that hurricanes keep testing and the town keeps rebuilding, and an Everglades frontier that gave the world the swamp buggy. Our Naples designs gather that identity into wearable form — the pier, the alligator, the 1886 founding, the Paradise Coast. From a newspaperman's American Bay of Naples to the pier that storms could never keep down — wear a little of the Old-Florida Paradise Coast.

Naples Florida — Travel Guide

Visiting Naples Florida Today

Naples sits on the Gulf of Mexico in southwest Florida, the seat of Collier County and the western gateway to the Everglades. Beyond the beaches and the boutiques, the old winter colony is still legible — Palm Cottage, the Naples Depot, Fifth Avenue South, and the long-running Swamp Buggy Races.

Heritage, Gardens & the Old Town in Naples Florida

For visitors searching for things to do in Naples, Florida:

• Tour Historic Palm Cottage (1895), the oldest house in Naples and home of the Naples Historical Society.
• Visit the Naples Depot Museum, the restored 1927 Seaboard Air Line railroad station.
• Stroll Fifth Avenue South, the revitalized historic main street of galleries, courtyards, and palm-lined blocks.
• Walk the Naples Botanical Garden's themed landscapes and wetland boardwalks.
• See the historic Naples Pier site at the foot of 12th Avenue South, where the 1888 landmark is being rebuilt once more following Hurricane Ian (its latest reconstruction is underway).

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.

For deeper reading on the Naples, Florida history described here — the Calusa and Seminole Gulf coast, the 1886 founding by the Naples Town Improvement Company under Walter N. Haldeman and John Stuart Williams, the "Bay of Naples of America" winter colony, the 1888 Naples Pier and its many hurricane rebuilds, Historic Palm Cottage (1895), the 1927 Naples Depot and the arrival of the railroad and the Tamiami Trail, the Fifth Avenue South revitalization, and the Swamp Buggy Races — it may be useful to consult (1) the Naples Historical Society (Historic Palm Cottage), (2) the Collier County Museums and the Naples Depot Museum, (3) the State Library and Archives of Florida and the Florida Division of Historical Resources, (4) the City of Naples clerk's records office, and (5) the local-history collections of the Collier County Public Library. For travel and visitor information, it may be useful to contact (1) the Naples, Marco Island & Everglades Convention & Visitors Bureau (Paradise Coast), (2) Visit Florida, (3) the City of Naples parks and recreation department, (4) the Florida State Parks office, and (5) the regional visitor and airport information desks.