Street Smart: Naples’s Fifth Avenue South

Naples, Florida’s Main Street for millionaires

The buildings are coral pink and canary yellow. Palm fronds shade sidewalk cafes, and old-fashioned lampposts line the promenade. Welcome to Fifth Avenue South, also known as Main Street to residents of Naples, a city that claims more millionaires per capita than any other in Florida. As you browse the avenue’s six blocks, you’ll find Versace for babies and monogrammed strollers for dogs. But you’ll also discover a family-operated cafe serving cheap homemade tapas and a shell shop carrying conchs plucked from the beach at the end of the road. The avenue has certainly grown up since the 1920s, when it was home to a garage and little else, but it remains accessible to those whose net worth hasn’t quite hit the seven-figure mark.



Dolce & Salato
Start your morning with a chocolate croissant and a cappuccino from this European deli, owned and operated by two first-generation Italians. Enjoy your breakfast on the covered patio with great views of the avenue, then browse the selection of imported wines, truffles, and olive oils.

Sheldon Fine Art
Pick up an original painting, photograph, or sculpture at this sunny gallery, best known for its nautical-themed works. Since the average temperature in Naples is 77 degrees, it’s no surprise you’ll also find a wide selection of paintings by local “plein air” (outdoor) artists.

Bella Maria Cafe
At this charming Chilean-Spanish cafe, the owners are also the chefs and servers. Family matriarch Maria Iribarren guards her sangria recipe zealously; order a pitcher from one of her sons, along with the pressed pork loin sandwich with avocado and tomatoes.

Little Luxe
If your mini fashionista simply must have something Fendi, you’ll find what you’re after at this children’s boutique. Despite its large collection of designer fashions, the shop is far from stuffy: Children watch cartoons while their parents browse the (great) sale racks.

Pucci & Catana
Celebrities like Rod Stewart frequent this posh puppy store for crystal-encrusted collars and faux-fur carriers. There’s even a special section for cats who love couture.

Tracy Negoshian
Tracy Negoshian

Erik Kellar

Tracy Negoshian
Visit the flagship store of this rising South Florida designer, whose tunic-style dresses have some calling her the “affordable Tory Burch.”

A hot new kid on the Old Naples block, this $3 million restaurant is centrally located next to the famed Inn on Fifth. Sit at the swanky bar and order a salad of fried green tomatoes, burrata, and micro basil. Wash it down with the signature “Filthy Rich Martini.”

The Blue Mussel
Best known for its wide selection of shells, this shop also offers sea-inspired gifts like model sailboats and ocean-scented candles. Splurge on a $600 piece of rare coral flown in from the Philippines, or grab a local starfish from the dollar bin.