Naples’s spectacular shoreline
Darron R. Silva/Visit Florida

Discover this classic resort town’s sassy new side, which includes a heady dose of Old Florida.

By Tracey Minkin
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“The New Naples” blogger Jennifer Adams
Courtesy of Jesse Adams

“The New Naples” blogger Jennifer Adams names 10 ways to do up her hometown in sun-drenched style.

Morning Coffee
There’s so much to love about Kunjani Craft Coffee & Gallery, mother-daughter duo Nicola and Stephanie Bunnett’s pale pink little coffeehouse/gallery across from Waterside Shops. The organic, small-batch coffees are roasted in Naples, the pastries are locally sourced, there’s a gallery of African art off the sunny courtyard, and the Bunnetts support a different nonprofit each month, both locally and in Africa. 

Historic Naples Pier
Fine Art Photos/Shutterstock

Play Time
In a town full of sophisticated pleasures, the Naples Pier stands out for its nostalgic appeal. Stroll the historic pier, watch for chevrons of passing pelicans, and then settle in on the adjacent white-sand beach: old-fashioned, lovely, timeless.

Beach Lunch
Despite its spectacular beaches, Naples has only a handful of restaurants right on the sand. Which makes a midday dally at the Turtle Club Restaurant, a beloved hangout on the grounds of the Vanderbilt Beach Resort (just north of the Ritz-Carlton) a must. Check out the Everglades Shore Lunch: blackened Gulf fish with lump crab over Turtle Club’s house seafood chowder, plus micro cilantro and preserved-lemon oil, all served with a tarragon-basil hush puppy. 

House Ogling
When in Naples, do Gordon Drive. Adams always encourages visiting friends to rent a bike or scooter and cruise the two-and-a-half-mile storied drive from the banyan-and mahogany-shaded downtown stretch, past colorful estates and the Port Royal Club, to Naples’s southernmost tip. (Ask locals about the house where the panther escaped.) 

The palm-graced streetscape of 5th Avenue South
Anne Rippy/Getty Images

Shopping Stop
Adams loves the historic stretch of 3rd Street South. Her must-stop: Marissa Collections, where owner Marissa Hartington exhibits her perfect touch with designer lines in her landmark, blazingly pink building. Also pink and perfect: A Mano, a collection of apparel and housewares tuned perfectly to the Naples vibe.

Late-Day Stroll
Tin City—a fishing village that’s been transformed into a collection of quirky, Old Florida–style shops and waterfront restaurants—is the ideal spot to post up at the end of the day to watch the fishermen come in, clean their catches, and throw scraps to the pelicans.

The Bum Boat tiki cocktail at Bar Tulia
Courtesy of Michael Caronchi of Caronchi Photography 

Happy Hour
Start the night with confidently crafted cocktails at Bar Tulia. While the interiors at this 5th Avenue South gastropub whisper “Italian rustic tavern,” and the menu represents on the osteria front, the cocktail menu is big-city savvy. (For example, the Ginrique Iglesias features St. George dry rye reposado gin, Cherry Heering liqueur, Angostura bitters, and Rhum Clément Creole Shrubb.)

Instagrammable Dinner
The eating is great at Timeless—An MHK Eatery. This newly opened food marketplace puts terrific coal-fired pizzas in the starring role among its series of sit-down, snack, and take-away options. But those interiors share the spotlight. Inspired by owner/residential architect Matthew Kragh’s vision of Old Florida vernacular, this loft-like, bright white eatery is New Naples at its best—and most photogenic.  

Related: Perfect Weekend in Palm Beach, Florida

Bay Brunch
A hidden gem, the Bay House is tucked among mangroves on the Cocohatchee River in North Naples. The waterfront deck is the ideal place to make your lazy way through an extensive raw bar menu.

Sunday Sunset
It’s an end-of-the-weekend tradition, Adams says, to meet for sunset at the Naples Beach Hotel & Golf Club, the town’s last big resort that’s still family owned, to hang out at the beach bar and dance to live music. The crowd is locals and tourists, old and young. And the party is pure Naples.

The white-sand meeting of pool and Gulf at The Naples Beach Hotel & Golf Club
Courtesy of The Naples Beach Hotel & Golf Club

Check In 
Love The Ritz-Carlton? You’re in luck: Naples is one of the only cities in the United States to have two of them. Set on three miles of powdered-sugar sand, The Ritz-Carlton, Naples has 450 guest rooms (including 35 suites) with beach and Gulf
of Mexico views. Nearby, The Ritz-Carlton Golf Resort, Naples, is home to the Tiburón Golf Club, with two 18-hole, Greg Norman–designed championship golf courses. Rates start at $199. 

The colorful cottage style of Old Naples
From Dream Houses: Historic Beach Homes and Cottages of Naples; Text by Joie Wilson and Photographs by Penny Taylor; Gainesville: University Press of Florida, 2011; Reprinted with permission

Stay for a Lifetime
Think Naples is all about sprawling Mediterranean mansions? Think again. Old Naples (largely the 34102 ZIP code) is home to classic cottages marked by deep roof overhangs, front porches, and wood siding. Absent regulation to protect them, many of these historic gems have been torn down and replaced with new construction. Which means finds like these on the market are rare, says Joie Wilson, author of Dream Houses: Historic Beach Homes & Cottages of Naples, and require love and investment. “It takes a very special homeowner,” she says.