Fifth Avenue South: Prime Dining, Shopping and Entertainment in Naples

Discover a trove of sumptuous dining options, luxe boutiques and acclaimed events on Fifth Avenue South, in the heart of Naples.

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A visit to Naples would be incomplete without a stroll along its unofficial Main Street, Fifth Avenue South. Since the 1920s — when it housed just a few small businesses, the telephone company and a train depot — the Avenue has been at the heart of the downtown district. Over the decades, it’s blossomed into the thriving business and arts district it is today, securing its spot as a prime dining, shopping and entertainment destination for visitors and residents alike.

Here are some of Fifth Avenue South’s most irresistible offerings.

Fifth Avenue South: The Shopping Destination

When you feel the urge to shop, Fifth Avenue South is the perfect spot for a little — or a lot of — retail therapy. You’ll find an incredible range of shops — from familiar favorites to locally loved boutiques — along a walkable stretch of Fifth that lies between Third and Eighth streets.

Whether you’re looking for the latest swimwear or accessories to complement the outfit you’re wearing out tonight, Fifth Avenue South features expertly curated boutiques where you’re bound to find the perfect clothing and accessories. 

Discover the latest from European designers at Marilyn’s, or let the relaxation flow with a breezy outfit from Petunias. Rouze brings trendy city style to the Avenue, while Giggle Moon offers unique, quality children’s clothing and accessories. Looking for must-haves from your favorite clothing line? Fifth Avenue South also boasts of beloved brands like Soma and White House/Black Market.

There’s no shortage of beauty products and services along the Avenue. With handmade skincare products that have garnered love from across the Sunshine State, Naples Soap Company is a must-visit. Take a little break with a mani-pedi at PAINT Nail Bar, or experience award winning ambiance, soothing treatments, and signature therapies at The Spa on Fifth.

If your walls are looking a little bare these days, Fifth Avenue South also offers an astonishingly diverse array of art galleries and home furnishing shops, like Native Visions Gallery, Emily James Gallery, Englishman Fine Art and more. 

Dining on Fifth Avenue South: From Italian Fare to Coastal Flair

Fifth Avenue South is home to many of Naples’ top restaurants, several of which have national accolades to their names. With fresh seafood flown in daily from Greece and across the globe, Sails Restaurant is sure to impress for special occasions. Dine al fresco in the courtyard at The French, which serves classic Parisian brasserie options, including Sunday brunch with live jazz. Love stone crab? During stone crab season (Oct. 15 through May 14), indulge in all-you-can-eat claws on Monday nights at Truluck’s. Fittingly for Naples, authentic Italian options are plentiful, including Pazzo! Cucina Italiana, Osteria Tulia, Molto Trattoria and Dolce & Salato Italian Bistro. 

For more casual dining options on Fifth, visit Yabba Island Grill for seafood and steaks or Fifth Avenue Coffee Co. and Sixth Street Diner, where you’ll find a variety of breakfast items, sandwiches and salads. Or cool off with a frozen treat at Gelato & C.o, Kilwin’s or Regina’s Ice Cream, a retro-inspired staple on the Avenue, best known for its old-fashioned ice cream sodas, malts and jukebox tunes.

When you’re ready for a cocktail, choose from the carefully curated menu of craft cocktails at Sidebar, which carries a chic lounge vibe, or the Italian gastropub Bar Tulia, or let talented bartenders mix a custom creation to suit your palate. (They’re also open for late-night dining after a night of dancing at Vergina.) 

Things to Do on Fifth Avenue South

There’s no shortage of fun here! Catch a live theater performance by The Naples Players at Sugden Community Theatre, or bring the kids to Cambier Park for a picnic and a free flick during summer’s monthly Family Movie Nights. Want to experience a true Naples hidden gem? Sit down for a traditional afternoon tea with scones and clotted cream at Brambles English Tea Room, tucked away among the lush flowers and fountains of the Rue de Fleur.

The Avenue becomes even more special on the second Thursday of every month during Evenings on Fifth. Enjoy an array of live musical performances along the sidewalk areas of the Avenue, explore distinct boutiques and galleries or relax with friends over dinner and dessert.

See more events and activities on Fifth Avenue South’s monthly calendar.

Where to Stay: Inn on Fifth & Beyond

Want to make a long weekend of it? Opt for a room at Inn on Fifth, which has long anchored Naples’ main thoroughfare. This Forbes 4-star boutique luxury hotel recently underwent a multimillion-dollar renovation that gave a sleek, fresh look to its 119 elegantly appointed guest rooms, including 32 Club Level suites, two Presidential suites, a private rooftop pool and a Club Lounge in a private building across the street from the main hotel. Guests can indulge at the on-site Spa on Fifth and get in a workout at its 24-hour fitness center.

Or, for a far-away feel, reserve your room at Hotel Escalante. Tucked away at the end of busting Fifth Avenue South, this boutique hotel is reminiscent of a Mediterranean villa, flush with poolside fountains, tropical gardens, and private patios and verandas perfect for a romantic getaway. It also features its own fine dining restaurant on site, Veranda E, which offers Asian-inspired cuisine with a French flair. Best of all? Both The Inn on Fifth and Hotel Escalante are within walking distance to the beach, not to mention all of the shops and restaurants lining Fifth Avenue South.

Explore more Naples area hotels, resorts and rentals.