What to do on a Naples beach vacation

Perhaps you just need a change of scenery.

Once you emerge on the other side of Alligator Alley after a two-hour drive, the west coast of South Florida unfurls against the powder white sands of the Gulf of Mexico where Naples is nestled into a corner of the Everglades. Here, you’re never far from a mangrove estuary as herons and brown pelicans swoop peacefully through the sky and you can consistently rely upon dolphin sightings just offshore.

It’s a favored destination of wealthy snowbirds and retirees—their stucco and limestone manses are built waterfront along the gulf and its canals. But there’s also a more down to earth year round locals scene to be discovered.

A view of downtown Naples on Fifth Avenue South.

After a long weekend there, I decided Naples has a touch of sophistication with its neatly landscaped Mediterranean Revival downtown district, and a touch of the rough-and-tumble as locals stream down the avenue on longboards, barefoot in cutoff jeans on their way to the beach.


Where to Beach

The boardwalk at Clam Pass Park that leads to the beach.

For Miamians accustomed to the Atlantic Ocean, a trip to Naples should involve the beaches of the Gulf of Mexico if only to be reminded of their difference and, more importantly, to relax. For an experience that feels like you’ve stumbled upon a secret stretch of beach, head to Clam Pass Park, a mangrove estuary at the foot of the Naples Grande hotel. After a 15-minute walk through a hardwood hammock along a boardwalk made of recycled milk cartons, I reached the sparkling aquamarine gulf and spotted a gopher tortoise and dune rabbit as soon as I reached the sand. There’s an open air Greek restaurant with shaded patio seating on a wooden deck, adding to the “paradise found” charm.

A popular beach for locals is accessed at the end of Vanderbilt Beach Road near the rowdy Beach Box Cafe. To the north, you’ll find The Turtle Club where you can enjoy dinner or drinks with your toes in the sand and front row views of the sunset and to the south, the Ritz-Carlton’s Gumbo Limbo tiki bar offers a casual, yet chic setting for oceanfront cocktails.


Dining & Nightlife Downtown

The thrust of Naples dining and nightlife scene is found downtown along Fifth Avenue South, along with its boutiques and galleries. I met friends at Bistro 821 for pre-dinner cocktails and appetizers where their espresso martini is extremely popular amongst locals. Already starving, I ordered their chili relleno stuffed with garlic shrimp, spicy beef and mozzarella smothered in a refined roasted tomato-chipotle sauce that perfectly hit the spot.

We moved onto Tulia for dinner, with its shabby chic décor, earnest cocktail program and sophisticated menu of sumptuous Italian small plates. It’s as close to hipster as it gets in Naples and would easily be at home amongst Miami’s hot spots with dishes ranging from house-made ricotta with artichokes and Meyer lemon to a simple cacio e pepe bucatini with sheep’s cheese and wood-roasted salmon. Across the street is Paddy Murphy’s Irish Pub, if you’d like your night to devolve into a drunken spiral in a strange, dimly lit pub-meets-club atmosphere.

Raw bar from Naples Grande’s Cath of the Pelican.

Otherwise, The Continental is a short Uber away on Third Street where a chic patio lined in white umbrellas hosts live music on Friday and Saturday nights and a sophisticated cocktail menu is organized by the spirit. This stretch of Third Street is worth exploring during the day for its chic shops (ranging from Oscar de la Renta to local boutiques) in a village-like setting. You’ll also find Sea Salt here, one of Naples’ hottest restaurants of the moment, specializing in sophisticated Italian by Venetian chef-owner Fabrizio Aielli.  



Lunchtime champagne at the Inn on Fifth’s Avenue 5 downtown.

Avenue Five at the Inn on Fifth offers an exceptionally sophisticated place to sip champagne in a champagne-colored dining room with floor to ceiling windows overlooking the street. Opt for their Lobster Cobb or duck confit flatbread. A more casual option is Shea’s at Landsdowne Street, tucked away in a plaza across the street from Avenue Five. This newly opened spot serves up a wide variety of sandwiches, salads and burgers alongside an extensive beer selection in a sports bar setting.


Where to Stay

A cushy bedroom at Naples Grande.

Naples Grand Beach Resort. With chic poolside landscaping that includes three pools and a water slide, Naples Grande also boasts a spa, golf course and beach access. Rooms are spacious and chic with balconies and a cool palette of blues, silvers and creams. Don’t miss a meal at The Catch of the Pelican with their decadent and perfectly chilled raw bar, farm fresh salads and prime cuts of steak paired with fine wines and peaceful views. From $246.

Marble bathrooms at Inn on Fifth.

Inn on Fifth. For a sophisticated stay in downtown Naples, the Inn on Fifth is decked out in a sophisticated Art Deco motif in black, white and red. Rooms and suites are spacious and stylish with large marble bathrooms. From $169.

Edgewater. This all-suite hotel is situated directly on the gulf for stunning sunset views (pictured at top). Take a paddleboard for a spin from their beach hut where you’ll spot dolphins along the nearby jetty. From $215.

Why Go:

For Miamians, a weekend in Naples offers a relaxed pace, the nature and tranquility of the Gulf of Mexico and some pretty hotels to hide away for a getaway that’s easy to pull off.

The Logistics: Two-hour drive from Miami across I-75 Alligator Alley.

Shayne Benowitz is Miami.com’s Travel Editor. Sign up for her monthly newsletter at ShayneBenowitz.com.