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. Overnight rates from $247 when booked three weeks in advance
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.
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. Overnight rates from $99
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!