Southwest Florida Weekend Getaway

The best places in Southwest Florida to stay, eat and play throughout the year.

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Watch the sunset from the balcony of Inn on 5th in Naples, Florida. Inn on Fifth

Naples Spa Seekers

Best For Spa-minded individuals.
Sleep The Spa at the Naples Grande Beach Resort focuses on holistic body rituals and customized Eastern-style massages. Bask in the Zen garden made up of rain showers, waterfall baths and a meditation labyrinth.

Fishing Pine Island

Best For Fishing buddies.
Sleep An old-school fishing lodge with upscale trimmings, Tarpon Lodge provides comfort—we love the island house, a building on stilts with views of Pine Island Sound.
Eat & Drink The lodge has one of the best blue-crab-and-roasted-corn chowders around. When you’re out and about on the waters, dock at Cabbage Key and hit the bar for a Cabbage Creeper—white rum, cream of coconut, coffee liqueur and pineapple juice. Check out the dollar bills pinned to the ceiling and walls with sayings like “Go Noles” written on them.
Play Tarpon is the premier catch here, but Native Attitude Fishing Charters will take you to waters where redfish, snook, tripletail, cobia and others—depending on the season—are biting. Don’t miss a group of wooden shacks on stilts off North Captiva Island. They’re still used by private fishermen for overnight excursions.

City Chic Naples

Best For A stylish escape.
Sleep At the Inn on Fifth, and there’s no need for an advanced itinerary. The best of Naples’ trés chic downtown is within walking distance: high-end shops and galleries, chef-owned restaurants and even the beach. The Naples Players community theatre, which offers year-round performances, is just a hop from the inn.
Eat Nosh on sliders and fries with hollandaise dipping sauce at Café & Bar Lurcat.
Play The Spa on Fifth‘s vinotherapy treatments capitalize on the antioxidant and anti-aging benefits of resveratrol and polyphenols, found in grapes, grape seeds and vines. Do People-watch from your Fifth Avenue-fronting balcony, or take a plunge in the city’s only rooftop pool. Diving into those divinely scented and oh-so-soft sheets for a quick catnap is also perfectly acceptable.

Casual Luxury on Siesta Key

Best For The high-style beach life. Siesta Key is renowned for its flour-soft sand, and as soon as the sun rises, the locals are out walking the Gulf of Mexico’s shoreline.
Sleep You’ll find plenty of vacation rentals here, but then there’s the Hyatt Siesta Key Beach resort—the only luxury six-story property on the six-mile stretch that will spoil you rotten. Call It Home For longer stays with the family, book the four-bedroom unit with a kitchen that any Food Network chef would kill for.
Eat Nearby Ophelia’s on the Bay serves waterside romance and a luscious blue-crab bisque. Request a table on the outdoor terrace skirting Little Sarasota Bay; keep an eye out for dolphin and long-legged waterfowl.
Play Complimentary bicycles let you cruise along Midnight Pass Road under banyan trees; along the way, you can peek into the backyards of some of the region’s most gorgeous beach houses. Go north and zip into Siesta Key Village to shop at funky stores for hats and flip-flops. Later, indulge in a big scoop of Kahlua Krunch ice cream at Big Olaf’s Creamery.

Natural Everglades

Best For Nature Lovers. Take a ride with Air Boat USA and practically skim the surface as you zoom deep into the River of Grass and its backcountry waters. Guides—some fourth-generation Floridians—provide colorful narratives.
Sleep Rent a stilt home at Glades Haven Resort in Everglades City.

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