Long celebrated as the crown jewel of Florida’s Gulf Coast, Naples combines white-sand beaches, multimillion-dollar estates and enough golf courses to fill several vacations. But look beyond the palm-lined avenues, and you will discover an evolving destination with a lot more to offer.
Peek a little closer, and you will find one of the nation’s great automotive collections, a 170-acre tropical garden, cool independent restaurants, a waterfront food-truck park and a pickleball complex with a staggering 65 courts. Even Naples’ late-night scene has grown, with cocktail rooms now keeping glasses raised into the wee hours.
The easiest way to arrive is through Southwest Florida International Airport in Fort Myers, approximately 35 to 45 minutes away by car. With no convenient passenger rail service into Naples, renting a vehicle or arranging a transfer remains the smartest move.
Make Naples Beach Club, A Four Seasons Resort your headquarters. The 220-room beachfront resort sits within easy reach of Old Naples and is loaded with reasons to lounge on-property. Guests can request one of its complimentary electric Mokes on a first-come, first-served basis — it makes a spin around town an open-air joyride, if you’ve never tried one.
Onsite, the tri-level Sanctuary Spa at Naples Beach Club holds a 3,200-square-foot thermal circuit with steam rooms, a Finnish sauna, a heated whirlpool, cooling elements, an ice lounge and experiential showers. Dining spans from seafood beside the sand at HB’s to Latin-inspired bites at Sunset Bar. And check out the latter’s lavish $100 Gulf Shore Margarita, made with Patrón El Alto, Grand Marnier Cuvée Louis Alexandre and lime that’s presented with a keepsake Yeti shaker.
When you pull yourself away from the property, here is how to give Naples a proper 48-hour spin.
Day One
Start at Wolfmoon, a bakery and coffee bar nestled inside Naples’ greenery-filled Kaleidoscope Garden Club. Croissants are essential here, with options ranging from classic almond to ones oozing with vanilla custard.
Your next stop is Naples Botanical Garden, a utopia of tropical flora from Florida, Brazil, Southeast Asia and the Caribbean. Hop on a guided tram tour if you’re looking to save those steps for later.
A few minutes down Bayshore Drive, Celebration Park is a waterfront gathering place built around a rotating fleet of food trucks. Grab lunch and claim a table overlooking Haldeman Creek.
It’s now time for a tough choice between horsepower and history. Automotive devotees should reserve tickets well ahead for Revs Institute, which opens Tuesdays, Thursdays and Saturdays. Its collection explores the automobile as a feat of engineering, a competitive machine and an agent of social change. Porsches, Ferraris, Ford GT40s and more are regularly in rotation.
For a look at the area’s past, there’s Historic Palm Cottage. Built in 1895 from tabby mortar — a mixture of sand, shells and water — the 3,500-square-foot structure is Naples’ oldest house.
From Palm Cottage, you are already near Third Street South and only a short ride from Fifth Avenue South — consider these Naples’ main drags. Spend the remaining daylight exploring both districts.
Third Street South, regarded as Naples’ birthplace, sits two blocks from the Gulf and is lined with boutiques, galleries, courtyards and restaurants. Fifth Avenue South is a livelier counterpart with additional shops, art galleries and cultural venues lining the strip.
For dinner, snag a courtyard table at Campiello, housed in the historic Naples Mercantile Building on Third Street South. Its rustic Italian menu centers on meats cooked over an open flame and regionally inspired morsels.
Naples does not shut down immediately after dessert. Sidebar pours cocktails in a stylish Fifth Avenue-adjacent room and, nearby, The Vine Room serves wine and cocktails overlooking Fifth Avenue South.
Day Two
Head north for breakfast at Three Sixteen, a specialty coffee shop and bakery near Wiggins Pass. A slate of breakfast fare fuels the morning, and then it’s over to one of Southwest Florida’s finest stretches of coastline.
Delnor-Wiggins Pass State Park occupies a barrier island where the Cocohatchee River meets the Gulf. Its beach is primed for swimmers and shell seekers.
After rinsing off the sand, choose an afternoon destination based on your retail appetite. Waterside Shops is Naples’ luxury option, with 60-plus retailers and restaurants, including Dior, Gucci and Hermès. For shopping with a broader entertainment roster, head to Mercato. The open-air complex has an Alamo Drafthouse Cinema, live music and seasonal happenings.
If two days of pastries, beach time and cocktails have you craving competition, drive south to the US Open Pickleball Championship’s home, the USOP National Pickleball Center. The center contains 65 outdoor courts, a pro shop, clinics, leagues and open-play sessions.
Finish at Nat Nat, an intimate natural-wine bar and kitchen along Tamiami Trail. Chef Ming Yee changes the menu weekly according to what local farms and fishermen supply. The restaurant recommends ordering the entire compact menu and letting the team match each dish with wine.
Sure, it is a bold ask — but after a couple of days of doing Naples properly, why hold back now?
