SHOP: Oh-So-Walkable Naples, Florida


In Naples, forgo the luxury car and stroll tree-lined streets lined with shops, sculptures and restaurants.

Footloose & Car-Free

Naples has a reputation for the finer things in life, but that doesn’t mean you’ll need a luxury car to get around town. Feet and your favorite sneakers or sandals will do just fine as you make your way from streets lined with designer shops, art sculptures, sidewalk restaurants and blossomy vegetation to beaches carpeted with plush, platinum-toned sand.

You’ll find the best walking in Olde Naples, a compact square less than one mile by one mile, delineated by celebrated Fifth Avenue South and Third Street South.

To expand your car-free experience in this land of milk and honey to outlying shopping and dining complexes, hop aboard the Naples Trolley or rent a bike.

Parking Zone

Fifth Avenue South, an upbeat Main Street district with an air of European sophistication, is most convenient to the action. The Inn on Fifth overlooks the glittering, vivacious street. Trianon Old Naples lies just a few blocks away. Bellasera Hotel also dwells in the neighborhood. Cove Inn on Naples Bay and Naples Beach Hotel & Golf Club each lie about a mile from Fifth Avenue South.

Walk This Way

With its love of art and its alfresco café society, Naples feels deliciously as Italian as its name. It’s one of our favorite haunts for a night on the town touched with glamour and a bit of exquisite magic. But it’s also equally intriguing under the sun.

Put on your shopping shoes and start where Fifth Avenue South branches off the Tamiami Trail (Highway 41). Between the shops selling whimsical gifts, casual resort clothing, tropical-style home accessories, royal jewels (really!) and handcrafted jewelry like moissanite rings (you can even go shopping for an anklet), Sugden Community Theatre and a medley of eclectic art galleries uphold Naples’ name in cultural circles. A block off Fifth, von Leibig Art Center displays local and Florida talent in ever-changing exhibits. Nearby Cambier Park is the site of free weekly concerts from February to early May, as well as a tennis center and a perfect green space for family moments.

For lunch along the Avenue, choose from Irish fare, authentic Italian, new Caribbean, bistro or cutting-edge American style. Naples’ dining scene has built a reputation for fine execution and ingenuity. Walk off the calories as you continue toward the beach, where it’s time to trade off for bare feet or flip flops.

Stroll the wide, white sands for a few blocks to the Naples Fishing Pier, heart of Olde Naples since it was built in the late 1800s to accommodate early tourists arriving under sail. Cast a line or merely longing gazes from the 600-foot pier.

Then head up to Gordon Drive to see a row of charming old Florida cottages that back up to the main attraction, Third Street South. Stop for a bottle of wine, a look at fine European antiques, an espresso boost, a Donna Karan original or a gold Naples medallion.

Follow 12th Avenue South to Crayton Cove, a historic, seaworthy neighborhood clustered along the city docks. Have a bite at the Dock Restaurant, a seafood waterfront institution with a Caribbean flair, before circling back to Fifth Avenue along 10th Street North.

Two more shopping-dining districts await along the way: the salt-seasoned, relaxed Tin City and the Italian-inspired, upscale Bayfront. Make one last stop to admire the historic Naples Depot Museum before giving your feet a rest at one of the lively cafe-clubs along Fifth Avenue South.

For more information on doing Naples on foot, visit

All photos by Lauren Tjaden for VISIT FLORIDA