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Courtyard arch, Third Street South, Naples FL

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The Charm and Appeal of Third Street South

This historic neighborhood in Naples, FL is home to chic stores and elegant dining

Everything about Naples, Florida is easy. It’s easy to get to, easy to navigate, the people are friendly and open, you can easily find a great meal, and even the beach—framing the Gulf of Mexico—is easy to walk on. The sand is firm, white, and solid and you can walk unobstructed for miles. 

And located just two blocks from those pristine beaches and the 19th-century Naples Pier is some truly excellent shopping and dining. Third Street South is a beautifully landscaped, historic neighborhood renowned for an abundance of chic shops, varied and award winning restaurants, and the hugely pleasant experience of eating dinner outside.

It was just after World War II that Junkie and Dorette Fleischmann bought the Mercantile Building (where the excellent Italian restaurant Campiello is now located) and turned it into an antiques market filled with European furniture and porcelains. They bought and built additional buildings—always adhering to the same attractive, Mediterranean revival design. 

In the late 1950s and 1960s the area began to fill out even more, adding art galleries and other interesting shops. The Fleischmanns were generous and interesting hosts and soon many of their friends in the publishing, theater, business, and international worlds started to make the trip south to visit. Among them were Broadway star Gertrude Lawrence, actress and radar-jamming inventor Hedy Lamarr, and Metropolitan Opera star Lawrence Tibbett. 

The Fleischmanns were an elegant couple and they translated their sense of elegance to the Third Street South destination. 

Carter and Finley, Third Street South, Naples FL
Upscale mens’ clothing store Carter and Finley. A focus on individual shops and their proprietors is a key part of Third Street South’s appeal. Photo by Nick Mele
Fleischmann Plaza with its 19th-century fountain, Naples, FL
Tobin transported an extraordinary early 19th-century Italian fountain from the garden of the family house to Fleischmann Plaza. Photo by Nick Mele

Joan Tobin, the Fleischmanns’ daughter who took over in the mid-1990s, has carried on their sense of sophistication and high standards. In keeping with the European appeal of cozy courtyards, and to honor her parents, Tobin transported an extraordinary early 19th-century Italian fountain from the gardens of the 1920s family house (Winding Creek Farm) to become a noted landmark in the heart of Third Street South.

A focus on well-known, sophisticated, individual shops and their proprietors is also a key part of the neighborhood’s appeal. Tommy Bahama’s founders built the first and flagship store on Third Street South in 1995, long before it was sold to a retail conglomerate. 

Tobin understands the importance of the continuity of design. “It’s like a beautiful room. It’s got colors that work well together with balance and create welcome.” She notes: “All I want is for this place, Third Street South, to be beautiful and attractive. I think once you’ve got that, the rest follows.” 

The logo, a graceful silhouette designed by the late Michael Vollbracht, the man who designed the famous Bloomingdale’s bag and took over Bill Blass, and who is a friend of Tobin, understood that she wanted to evoke the beauty and grace of the 1930s through the 1950s—and to recall the glamorous age that Dorette and Junkie Fleischmann lived and that they embodied. Vollbracht then recreated the same glamor-evoking dress often worn by international model and Naples native, Laken Romine in the Third Street ads. 

“All I want is for this place, Third Street South, to be beautiful and attractive. I think once you’ve got that, the rest follows.” 

Tobin is focused on continuing to spread the word globally about the hidden gem that is Third Street South—and it’s working. Now when she goes for a quick espresso at the local Tony’s Off Third Bakery or Bad Ass Coffee of Hawaii, she hears, “all kinds of different languages. And then I try to figure out which one it is. The last one I heard, I think, was Danish or Norwegian.”

Tobin carefully edits the mix of unique shops often found in Palm Beach, the Hamptons, and other high-end locations. Among them, the couture and jewelry boutique Marissa Collections, A Mano, the Tuscan furniture and decorations at Patina, the iconic, long-time favorite, Lily Pulitzer, the slim pants and Indian sari jackets at Charlotte Kellogg, and a just-arrived store, Marina St. Barth, as well as the Esquire-awarded men’s store, John Craig. 

To that end, Third Street South has put on a pop-up collaboration of Nick Mele’s iconic photographs in collaboration with vendors who create what you find in the world that Mele photographs. Now until March 31, 2024, Ala von Auersperg, Well Made Home, Cameron Silver’s Decades Vintage Store, and many others will bring fashion, interiors, decorations, accessories, and jewelry, popping in for trunk shows and special events.

Additionally, 10 percent of all sales will be donated to Women Lifting Women—a fundraising initiative of the Women’s Foundation of Collier County, to help senior women who find themselves homeless—and Neapolitan Enterprises, Tobin’s family company on behalf of Third Street South, will provide a match.

Of course, this is all being done with an eye to the future. And the future of Third Street South rests firmly in the hands of the next generation—Joan Tobin’s children, Alexis and Ian, who are collaborators and have strengths that complement one another. 

Cyclists on Third Street South, Naples FL
Third Street South’s delights are surrounded by lush, colorful flowers and landscaping. Fit in a quick cycle ride between shopping trips and dining out. Photo by Penny Taylor
A Mano store, Third Street South, Naples, FL
A Mano is one of the many fashion, interiors, decorations, accessories, and jewelry names participating in the pop-up, “La Bonne Vie.” Photo by Nick Mele

Alexis notes, “Continuing my family’s ‘legacy’ in Naples has never been something I expected to do but rather something I have been preparing for and looking forward to since I became fully aware of how important but also how interesting it is to run a business such as ours.” She goes on to say, “All of us, the  people who work with my mother (and now my brother) understand the combination of tradition and current chic, the beauty of the flowers and landscaping, and the welcome of the courtyards and fountains and the pleasure they bring.”

Alexis and Ian have a great friendship as siblings and business partners. Alexis focuses on the creative/production side of things—which complements her brother’s pragmatic side. “I also think we are both a reflection of our mother’s strongest traits—her incredible work ethic, her experience, and also her vision for the area which she has brought to life beautifully over the last 30 years,” says Alexis. “She’s taken things a long way from the original roots her father planted for us in Naples and my brother and I hope to continue that trajectory for the foreseeable future.” 

Hero photo by Nick Mele

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