Naples Pier Beach
Inn on Fifth
For a Beach Escape: LaPlaya Beach & Golf Resort
Perched on the shores of Vanderbilt Bay, this charming Southern-style haunt is a sea of spacious Gulf-view rooms, blue-striped cabanas, sparkling rock-waterfall pools and even a guest-only 18-hole golf course. Spend your days pampering yourself in the spa or lounging on the sand, the latter of which comes with a personalized beach butler who promises to never let your piña colada run dry. When you see signs of dusk, head to the delicious and award-winning on-site restaurant, BALEEN, for a sunset toes-in-the-sand dinner.
The Details: Overnight rates from $247 when booked three weeks in advance, @laplayanaples
For Comfort Food: Old Naples Pub
Located off Third Street South, this casual-meets-family-fun neighborhood favorite has been serving up hearty pub fare for more than 25 years. For the ultimate lunch, pair a frosty mug of whatever’s on tap with The Naples Pier Burger featuring a short rib, brisket and prime chuck patty topped with Gorgonzola cheese and thick, hardwood smoked bacon.
For a Round of Golf: LaPlaya Golf Course
One of Naples’ newer courses, the 18-hole LaPlaya Golf Course is an oasis of rolling-green hills, lush fairways, brightly colored bougainvillea and tropically tinged lakes. Designed by renowned golf-course architect Robert Cupp, this members-only locale plays host to The Leadbetter Golf Academy, which trains avid golfers with its short-game practice facility; separate pitching, chipping and putting green areas; and top-of-the-line V1 Golf swing analysis technology.
The Details: @laplayanaples
For A Quick Getaway: The Cove Inn
This quaint, beach-inspired hotel overlooks Crayton Cove, has a waterfront pool and Chickee Bar, and boasts cozy rooms and balconies with nautical-blue views. Perfect for a weekend escape with friends and family, it’s just steps away from posh Fifth Avenue South and is home to the diner-style Coffee Shoppe, which has a hearty menu of pancakes, omelets, French toast and more that hungry patrons will wait hours to taste.
The Details: Overnight rates from $99 this fall, @coveinnatnaples
For Happy Hour: Gumbo Limbo at The Ritz-Carlton, Naples
With its vibrant sunset views and casual-chic vibes, the gulf-front Gumbo Limbo, at The Ritz-Carlton, Naples, is a must-do for locals and visitors alike. Grab a seat at one of its open-air tables, or follow the turtles to the sand and belly up to the Sand Bar with a Gumbo Punch: spiced rum, banana liqueur, orange and pineapple juices, grenadine, and a dark rum floater. Bottoms up!
The Details: @ritzcarlton
For a New Bathing Suit: The Beach House of Naples
A tiny boutique tucked in Downtown Naples, this en vogue swim and resortwear shop has everything from kate spade new york and Vince Camuto to Tory Burch and Michael Kors. Tease yourself by browsing its couture racks, but head to the back corner for the real buried treasure: many of those designer tags at mega-reduced prices!
For a Girls’ Lunch: Jane’s Cafe on Third
A whimsical enclave in the heart of Third Street South, this casual eatery’s bright-pink and orange exterior; wrought-iron garden tables and chairs; and intimate courtyard of lush, overgrown flowers and shade trees are hard to miss. Its Alice in Wonderland feel is the perfect backdrop for this gem’s long menu of creatively light eats—like hearty breakfasts, organic salads, fresh and indulgent sandwiches and even a sumptuous afternoon tea.
The Details: @janescafeon3rd
For Sunset Views: Naples Pier
When the sun sets in Naples, locals and sightseers alike make their way to historic Naples Pier. Located at the west end of 12th Avenue South, it’s free to visit; is one of the most photographed spots on the Gulf Coast; and caters to crowds with its restrooms, concession stand, beach toys, covered eating area, and ample space for avid fisherman to cast out their nets.
For Late-Night Bites: Osteria Tulia
For a rustic Italian feast with a chic, modern twist, Osteria Tulia’s Brussels sprouts caramelized with housemade fennel sausage; Sicilian meatballs with pine nuts and currants; and orecchiette pasta with slow-braised hen, chicken liver, milled vegetables and Parmigiano—all paired with a “Fiore” limonata-St-Germain cocktail—should do the trick. Embodying the look and feel of a restored Italian farmhouse, this is the only eatery in Downtown Naples that serves a full menu until midnight.
The Details: @osteriatulia
For a Weekend in Luxury: Inn on Fifth
An iconic mainstay in the heart of Fifth Avenue, this classic Naples hotel is steeped in glitz, glamour and sophistication. Setting a new standard of luxury for South Florida, it underwent a $20 million expansion project in 2012, which added a new building of Club Level Suites. Expect 32 spacious and extravagant suites with a 24-hour concierge, separate check-in, private rooftop hot tub and sunbathing area, bespoke decor, complimentary Champagne and foodstuffs all day long, and up to 1,160 square feet of living space.
The Details: Overnight rates from $155, @innonfifthnaples