If these sidewalks could talk!

Over the decades, Fifth Avenue South has flourished and reinvented itself. One thing hasn’t changed though,Fifth Avenue South is still the heart and soul of Naples. The gathering and meeting place. Where businesses thrive, day-to-day life happens, and a vibrant nightlife is found. Where an afternoon errand may include a stop at the beach to watch the stunning sunsets.


If these sidewalks could talk, they would tell you that, since the 1920s, Fifth Avenue South has been Naples’ ‘main street.’

At that time, ’main street’ consisted of a few businesses located on Fifth approximately 3 blocks east and west of Ninth Street South – Ed Frank’s Garage and his small block of shops, the Chamber of Commerce, telephone company, train depot, Jack “Doc” Prince’s Naples Liquors, a gas station, Hixon’s Sundries and Club 41. The junction of Fifth Avenue South and Ninth Street South (aka U.S. 41 and the Tamiami Trail) was known as “Four Corners,” where, in 1948, Naples’ first traffic light was installed!

Our sidewalks would tell you the tale of the Frank family. In 1923, Ed Frank’s Garage near Tenth Street was the first commercial building on Fifth Avenue South. The Franks lived upstairs and Mrs. Frank would throw her table scraps to alligators in the swamp below. One of the first settlers in the area, the Frank family owned Naples’ first car dealership, and Ed invented the first swamp buggy!

The Orange Blossom Special first rolled into the Naples Seaboard Air Line Passenger Station on January 7, 1927. The last train to leave the Depot was in 1971 when the service was discontinued. Now, fully restored to its original elegance, the building today houses the Naples Depot Museum. The museum welcomes visitors back to the railroading boom days of the Roaring Twenties and explains how generations of Southwest Floridians used trade and travel to transform Naples into the Gulf Coast destination it is today.

Anyone familiar with Naples won’t be surprised to learn that, by the early 30s, there was a small golf course located at the end of Fifth near the beach. It was in 1932 that a plane piloted by Charles “Lucky” Lindbergh landed somewhere on those links! The Lindberghs had a retreat on Sanibel Island and would drop in to pick up supplies.

In the early days, Club 41 was a favorite of locals and visitors alike. Our sidewalks would gossip that, according to rumor, Gary Cooper, Lawrence Tibbets, Gertrude Lawrence and perhaps Gloria Swanson were among the guests who frequented the Club.

A member of the Seminole tribe, Cory Osceola and his family used to set up a stand and sell their crafts on Fifth Avenue South. The descendants of the Osceolas, a well-respected, old native American family, are now world-renowned builders of chickees (cypress pole constructions with palmetto-thatched roofs), and many of their structures stand in Southwest Florida and the Caribbean.

In 1929, the telephone company occupied a small building at the corner of Fifth Avenue South and Eighth Street. By 1945, there were 17 telephones in town! In 1968, the United Telephone Company built a new structure around the original structure, and, today, one of Naples’ finest steakhouse, Bistro 821, answers the phone at that location.


The sidewalks of Fifth Avenue South got an earful at The Rexall Drug Store on the corner of Fifth and Eighth Street South!

The benches in front of the store were a meeting place for local businessmen while the comic book racks inside the drugstore were a meeting place for local children!

In 1949, the town’s first bank, The Bank of Naples, officially opened for business on Fifth Avenue South, diagonally across the street from the telephone company. Assistant cashier, Mamie Tooke, often called the Mother of Naples, was instrumental in teaching residents how to budget and save their money, and many of those original depositors became large landowners! In 1989, The Bank of Naples became Barnett Bank, and today is Bank of America.
A family synonymous with Naples and with quality service had their business start on Fifth Avenue South in the 1940s and 1950s with the Sunshine Supermarket which operated at the corner of Fifth Avenue South and Seventh Street for many years. Today the Wynn family still owns the property and has expanded their business holdings to include Sunshine Ace Hardware and Wynn’s Grocers, still a part of downtown.

By the late 1940s, downtown Naples and Fifth Avenue South were becoming not just a place for commerce, but a cultural destination as well. In 1949, the development of Cambier Park was underway. Today the Park is a destination for concerts, festivals and movie nights along with providing venues for tennis, play, picnicing and shuffle board! Located today along the edge of the park are two world-class cultural destinations—the von Liebig Art Center and the City’s Norris Center featuring The Gulfshore Playhouse.


Fifth Avenue South continued to flourish during the 1940s, and 1950s.

In 1960, Hurricane Donna struck the Gulf Coast and impacted a number of the buildings and landscape of Fifth Avenue. By the mid-1960s Fifth Avenue was making a come-back and a real estate boom was in full swing.

As the late 1960s and 70s rolled around, newer more modern shopping centers were popping up on the outskirts of downtown creating new destinations for shopping, dining and entertainment. Fifth Avenue South continued to flourish well into the early 1990s, but felt the impacts of growth outside of downtown.

In the early 1990s, Naples-area business owners and civic leaders recognized the importance of a cohesive plan for the Fifth Avenue South district and engaged the assistance renowned urban planner and architect Andres Duany. With his guidance, an already fashionable street was transformed into Southwest Florida’s premier shopping, dining, cultural and performing arts destination.

The cultural renaissance fully took root in 1997 with the opening of the Sugden Community Theatre in the heart of Fifth. Home to the Naples Players, the Sugden Theatre planted a seed that has helped Fifth Avenue South develop into an enviable cultural scene with a focus on arts and music.


If these sidewalks could talk, they would invite you to stroll up and down The Avenue under clear blue skies, stopping to shop, chat, meet a friend, get a bite to eat and enjoy life in Naples, as locals and visitors alike have been doing for nearly a hundred years!

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Timeless Charm. Downtown Chic.

Fifth Avenue South is an irresistible mix of glamour and laid-back ease. Historic and modern architecture blend together in eclectic sophistication; tropical blooms and lush greenery grace its pedestrian-friendly promenades; and each storefront is filled with wonderful finds and delights.