Historic sites in Naples, all within walking distance

Today we’ll take a walking tour of Naples, which starts at a historic railroad depot and ends at the Gulf, in what is known as Olde Naples. Put on some comfortable shoes and come along.

Read more Blessing of the Pets set; CROW mourns ambassador, releases gallinule

Naples Depot1051 Fifth Avenue South, Naples

The Naples Depot Museum opened in 1927 as the southern-most west coast terminal for the Seaboard Air Line Railway, transforming early Naples from a small village into a growing winter resort.

Tin City1200 5th Ave S., Naples

Started in the 1920s as a working waterfront and commercial fishing hub along the Gordon River. The construction of the Seaboard Air Line Railroad and the Tamiami Trail turned the rustic, tin-roofed buildings into a major transport and economic center.

Fifth Avenue Shopping DistrictFrom Tamiami Trail to the Gulf of Mexico in Old Naples

Naples Fifth Avenue South began as a sleepy Gulf Coast dirt road in the 1920s. Today it’s the luxury retail and dining hub of downtown Naples, stretching from Tamiami Trail to the Gulf of Mexico in Old Naples.

Fisherman’s Lodge239 Broad Avenue, Naples

Fisherman’s Lodge is a historic two-story Dade County pine cottage built in 1919 located in historic Old Naples. Though not originally built on its current plot, the lodge was later moved to its permanent home in the historic district of Old Naples.

Read more Mark Woods: 43 years, thousands of stories, one last column

Periwinkle Cottage123 11th Avenue South

Periwinkle Cottage is a historic 1935 “beach home” located in the heart of Old Naples. It was built in 1935. The property features Old Chicago Brick and a classic white picket fence.

Palm Cottage 137 12th Avenue South

Palm Cottage was built in 1895 and stands as the oldest house in Naples. Louisville Courier-Journal Walter N. Haldeman had the home built. The grand structure features 12-foot ceilings and served as a winter retreat and guest overflow annex for the nearby Naples Hotel.

Other historic homes to see

• Timken House, aka The Tile House, located at 8th Avenue South near Gulf Shore Boulevard, was built in 1925. It was designed by architect Phineas Paist, who is known for his work in Coral Gables, Florida, including the Venetian Pool and the University of Miami’s original campus.
• Hewitt House is a one-story frame beach cottage built in 1913 at 926 Gulf Shore Boulevard. It’s equipped with heavy exterior shutters designed to protect against storms.
• Mandalay House, located at 1144 Gulf Shore Boulevard, is a large beach house built in 1908.
• The Whayne House, located at 88 11th Avenue South, is a luxury residence built in 1933.
• Westhaven, 1920, a massive bungalow located at 157 11th Avenue South. It was built on four lots by Colonel Robert West.
• Martha’s Cottage, located at 205 11th Avenue South and built in 1922, it was nicknamed by its original owners, drawing a connection to Martha McDonald – longtime inhabitant of a notable early beach home just north of the Naples Pier; known as “the Welkin-on-the-Gulf.”
• Honeymoon Cottage at 88 Broad Avenue and built in 1935 is a two-story cedar shake building with a steep gable.

Sources: Naples Historical Society, the Naples Daily News archives, newspapers.com and the State Archives of Florida.

This article originally appeared on Naples Daily News: Historic sites in Naples, all within walking distance

Read more Florida’s first congresswoman had ties to Volusia, Flagler

Reporting by Compiled by B.D. Green, Naples Daily News / Naples Daily News

USA TODAY Network via Reuters Connect

Copyright Reuters or USA Today Network via Reuters Connect

This story was originally published September 20, 2026 at 5:08 AM.