As Naples celebrates its 100th anniversary with events citywide, the Fifth Avenue South Business Improvement District salutes our fair city and is proud to be a part of its storied and remarkable history.

Fifth Avenue South, our original main street for the last 100 years, has enjoyed the distinction of being the major artery in the heart of downtown.

The Avenue was just a spot in the road when Naples was incorporated in 1923. The main street consisted of a few businesses about three blocks east and west of 9th Street South, including Ed Frank’s Garage, the Chamber of Commerce, the telephone company, the train depot, Jack “Doc” Prince’s Naples Liquors, a gas station, Hixon’s Sundries and Club 41.

Ed Frank’s Garage near 10th Street was the first commercial building on Fifth Avenue South. The Franks lived upstairs, and Mrs. Frank, as we are told, 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.

Above: The Pier

On January 7, 1927, the Orange Blossom Special first rolled into the Naples Seaboard Air Line Passenger Station, and service continued until 1971. The train depot ultimately became a museum.

In the 1930s, there was a small golf course located at the end of Fifth Avenue South near the beach. In 1932, Charles Lindbergh landed his plane somewhere on those links. The Lindberghs had a retreat on Sanibel Island and would often “drop in” to pick up supplies on Fifth Avenue South. During this time, Club 41 was a favorite of locals and visitors alike. Rumor has it Gary Cooper, Lawrence Tibbetts, Gertrude Lawrence and perhaps Gloria Swanson frequented the Club.

Above: Four Corners

Fifth Avenue South continued to flourish during the 1940s and 1950s. In 1949, the town’s first bank, The Bank of Naples, officially opened for business on Fifth Avenue South, catty-corner from the telephone company. Assistant cashier Mamie Tooke, often called the Mother of Naples, taught residents how to budget and save their money. Many depositors later became large landowners. In 1989, The Bank of Naples became Barnett Bank, and today is Bank of America.

In 1948, Don Wynn took a big financial risk and moved the Sunshine Market from the Naples City Dock area to Fifth Avenue South, where he opened the first modern grocery store where Yabba’s restaurant and the Sugden Plaza exist today. The store was a one-stop operation with a butcher shop, baked goods, and everything you could want in terms of groceries. Previously, Naples’ residents had to drive to Fort Myers to find the same offerings.

The store was so successful, that five years later the Wynns built an even larger one where Kilwin’s ice cream and chocolates and Best of Everything are today. The original grocery store site became Sunshine Hardware. Eleven years later, with business booming, both stores were moved to U.S. 41.

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 nearby Cambier Park was underway. Today, the park is a destination for concerts, festivals, and movie nights along with tennis, plays, and picnics. The park borders two world-class cultural destinations—the Naples Art Institute and the Norris Center featuring The Gulfshore Playhouse, which is now constructing a stunning world-class professional theater on Goodlette Frank Road.

In 1960, Hurricane Donna struck the Gulf Coast, damaging a number of buildings and landscaping on Fifth Avenue South. By the mid-1960s, Fifth Avenue South was making a comeback, and a real estate boom was in full swing. Unfortunately, newer more modern shopping centers were popping up on the outskirts of downtown, creating new destinations for shopping, dining, and entertainment.

While Fifth Avenue South continued to flourish well into the early 1990s, it felt the impact of growth outside downtown. Naples-area business owners and civic leaders recognized the importance of a cohesive plan for the Fifth Avenue South district and engaged the assistance of renowned urban planner Andrés 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. Home to The Naples Players, the Sugden Theatre planted a seed that has helped 5th Avenue South develop into an enviable cultural scene with a focus on arts and music.

Over the decades, Fifth Avenue South has flourished and reinvented itself. Today, if these sidewalks could talk, they would invite you to stroll up and down our charming avenue under clear blue skies, stopping to shop, meet a friend, get a bite to eat, and enjoy the best of life in Naples, as locals and visitors alike have been doing for a hundred years!