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AAA Traveler Worldwise | Southeast States
An Inside Look at Luxury Naples


Cruising down the avenue, I feel as if I’ve driven onto the set of the iconic TV show Lifestyles of the Rich and Famous. Block after block, well-heeled patrons in stylish resort wear à la Lilly Pulitzer and Tommy Bahama pop in and out of posh boutiques and art galleries and dine alfresco at charming cafés and swanky restaurants housed in modern Italianate buildings. And parked along or parading down the palm-fringed avenue, a smattering of head-turning sports cars—a Lamborghini, a Maserati and an Aston Martin among them—gleam in the balmy October sun.

5th Avenue South street sign5th Avenue South in the heart of Old Naples is a shopping and dining hot spot; Photo by Fotoluminate LLC/

Luxury is so abundant that you can almost hear Lifestyles host Robin Leach sending out his signature sign-off: “Champagne wishes and caviar dreams!”

Of course, this is no film set; this is 5th Avenue South in the heart of downtown Naples, which sits, pedestal-like, on the shores of the Gulf of Mexico in Southwest Florida. Naples was named such by early developers who were captivated by the beauty of the city’s bay, finding it reminiscent of—and, it’s said, arguably superior to—the bay in Naples, Italy.

It’s hard to imagine that Hurricane Ian came barreling down this very street a little more than a year ago. Today, barely a sign of the beast remains. A portion of the historic Naples Pier, which Ian hurled to the Gulf floor, has even been rebuilt and reopened to visitors already.

My sister, Stephanie, and I had come to Naples on a whirlwind getaway to experience a little of its luxe life, from beach-going and shopping to dining and unwinding. What we soon discovered, however, is that, while Naples has tony down to a T, luxury is only one of the many facets that makes this polished city the gem of Florida’s Paradise Coast.

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Naples blue Gulf watersNaples boasts miles of soft white-sand beaches and endless blue Gulf waters; Photo by lunamarina/

While pockets may run deep in Naples, so, too, does history. It’d be an understatement to say that General John S. Williams, a senator from Louisville, Kentucky, and Walter Haldeman, owner of the Louisville Courier Journal newspaper, got the deal of the century in the late 1800s when they purchased 3,712 acres of land, stretching from the Gulf to Naples Bay, for $11,136—a mere $3 an acre—to establish a winter retreat.

While that real estate would change hands over the following decades, it wasn’t until the mid-1950s, when returning World War II 
veterans bought homes and began businesses here, that Naples earned a prominent pin on the tourist map. Today, visitors can delve into that rich past at the Collier Museum, the Naples Depot Museum, and the Naples Historical Society’s Historic Palm Cottage, the city’s oldest house, built in 1895.

The luxurious Inn on Fifth houses the Ocean Prime restaurant on desirable 5th Avenue SouthThe luxurious Inn on Fifth houses the Ocean Prime restaurant on desirable 5th Avenue South; Photo courtesy of the Inn on Fifth

History would have to wait for Stephanie and me, though, because we had our own history to catch up on. The last time we vacationed together was when we were teens, probably squabbling over who got the top bunk at our beach rental. Now, decades later, we had made our home away from home at the Inn on Fifth, a boutique-style hotel with 119 guest rooms that has earned AAA Four Diamond status for the past 10 years. Translation: Luxury is woven throughout, from the 150-year-aged French oak flooring to the shimmering chandeliers bedecking the two-story lobby.

There’d be no quibbling over who slept where in our elegant 600-square-foot club-level suite, located in a separate building across from the main inn. Queen-size beds with plush Euro-top mattresses—check. A spa-like bath with a soaking tub—check. A lounge area with an L-shaped sofa leading to a private balcony overlooking 5th Avenue South—check and check. Club level also meant access to a rooftop patio with a hot tub (along with the pool, spa and fitness center in the main building); daily breakfast, snacks, hors d’oeuvres and a well-stocked self-service bar; and complimentary valet service around town.

Naples Botanical GardenThe Naples Botanical Garden is a tropical oasis; Photo by Stacy Tillilie

While we’re tempted to linger at the inn, Naples beckons, so we hit the town. First things first: the beach, just a six-block walk from the inn, past rows of meticulously manicured mansions dripping with character. There’s just something therapeutic about powdery-soft sand, turquoise-blue waters and sisterly conversation that money can’t buy.

Come evening, we stroll 5th Avenue and neighboring 3rd Street South, oohing and aahing over local artwork that’d look fabulous 
in our fairy-tale homes. Famished, we duck into an inviting trattoria where we snag a sidewalk table and enjoy house-made pasta, red wine and warm memories.

The following morning, we’re painting the town…well, green at the 170-acre Naples Botanical Garden. Here, we meander through a tropical wonderland teeming with plant life from Florida and around the world, including the Caribbean, Brazil and Asia. The lush greenery is so enveloping that, we laugh, it feels as if we’ve entered Jurassic Park—swap out dinosaurs for the possibility of some alligators in the garden’s lakes and ponds.

Lobby Bar at The Ritz-Carlton, NaplesThe Lobby Bar at The Ritz-Carlton, Naples, offers a curated assortment of wines and champagnes; Photo courtesy of The Ritz-Carlton, Naples

It’s almost lunchtime, and we can’t think of a better place to dine than at the beachside Ritz-Carlton, Naples. Reopened this past July after a nine-month shuttering in the aftermath of Ian, the AAA Five Diamond property is grander than ever, with a soothing coastal aesthetic threaded throughout its 474 reimagined guest rooms and indoor and outdoor gathering spaces. It doesn’t get more luxurious than this, with three new restaurants (adding up to a total of eight eateries) to try as well as 70-plus club-level suites in the newly built Vanderbilt Tower, touting the company’s largest club lounge on the continent, replete with floor-to-ceiling windows for those amazing Gulf views, a full-service bar and an artfully designed kids’ play space.

In go-big-or-go-home hospitality fashion, the glamorous hotel greets guests with its Lobby Bar featuring a Master Sommelier–curated tasting experience of champagnes and wines paired with delicacies such as oysters and caviar. Three revamped pool areas cater to guests with cabanas and 10 air-conditioned bungalows with private baths and entertainment systems.

Stephanie and I dine at the new open-air Sofra, offering a vegetable-forward menu of Eastern Mediterranean plates. Among the must-tries are the house-made flatbread and hand-pressed olive oil, onion rings piled high and sprinkled with barrel-aged feta, a hearty zucchini burger, and hummus made from a recipe belonging to the chef’s mother.

If we were golfers, we may have zipped the 3 miles over to The Ritz-Carlton, Tiburón, home to two 18-hole courses certified as an Audubon Cooperative Sanctuary and—bonus—a water park with a winding river and waterslides. (No Tiburón tee time? No worries—the greater Naples area has some 90 golf courses, with many open to the visiting public.)

Gurney Eagle exhibition at Rev Institue, NaplesThe Revs Institute presents a wealth of fascinating vehicles—and the stories behind them; Photo by Stacy Tillilie

We are, however, car enthusiasts. (Growing up with a father in the auto business, we figure it must be in our DNA.) So, we swing by the Revs Institute, part working restoration facility, part library and museum showcasing the Miles Collier Collections with some 100 rare and historically significant automobiles from 1896 to 1995—all in peak running condition. As we explore three floors of ingeniously designed vehicles, volunteer docents share the fascinating stories behind them, from turn-of-the-century tourers to racing cars that triumphed at Le Mans to a more modern-day McLaren.

If we had more time—our newbie mistake—we would’ve perused the contemporary art at the nearby Baker Museum and dropped by to see the wildlife and botanical exhibits at the Naples Zoo at Caribbean Gardens. But our ship…err, yacht had come in, and it was almost time to check in for a sunset wine-and-hors d’oeuvres cruise.

A palette of pretty canals and colorful architecture creates an enchanting cityscapeA palette of pretty canals and colorful architecture creates an enchanting cityscape; Photo by Info Creates/

After freshening up at the hotel, we take advantage of its valet service, which drops us off at the Port-O-Call Marina, home of the 105-foot-long, 149-passenger Naples Princess. Before boarding, we jaunt next door to Old Florida-style Tin City, where we breeze through the souvenir shops and amble along the docks.

Once aboard the Princess, we take our glasses of pinot noir and find two empty chairs on the bow of the boat alongside a small group of sociable women celebrating a birthday. A few of them who’ve taken this cruise before congratulate our fortune 
of landing front-row seats.

Soon, we’re off, sailing Naples Bay, the canals of Port Royal and the Gordon Pass before dipping into the Gulf of Mexico. Along the way, we pass mangrove forests, frolicking dolphins and strings of wow-worthy waterfront properties. As we point out our favorite homes, our new friends tell us not to “settle” yet, as the ones farther out are even more stunning. And they are.

But the real showstopper is the setting sun, glowing gold and slipping ever so gracefully into the Gulf. It’s an occasion worth toasting—to the precious beauty and blessings of family and friendship—and maybe even, every now and then, to a few champagne wishes and caviar dreams.