- Step in the sand, get behind the wheel, sink a putt, swim on a reef, learn to sail or play with a dolphin. Our guide to the hottest weekend getaways in the Sunshine State gives you the best that Florida has to offer, one weekend at a time.
- The Weekend: Go fishing at Pine Island. Pine Island may not have a single beach, but you’ll hardly notice while napping on a hammock or fishing along the 17-mile island’s coast.
Start Here: 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. (You’re so close that the waves will lull you to sleep.) Get fortified with a complimentary continental breakfast at the 1926-built historic lodge building before heading out for the day.
1. Fishing is number one on your to-do list. 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. While you cruise, keep an eye out for the wooden shacks perched on stilts off North Captiva Island; they’re still used by private fishermen for overnight excursions.
2. Every boater knows that being on the water whets your appetite. Instead of packing your own, dock at Cabbage Key for burgers and a Cabbage Creeper: white rum, cream of coconut, coffee liqueur and pineapple juice. This spot is pure Old Florida; decoration comes courtesy of dollar bills pinned to the ceiling and walls with sayings like “Go Noles” written on them.
3. For dinner, get your seafood on with dinner at the Tarpon Lodge’s four-star restaurant, serving up the best blue-crab-and-roasted-corn chowders around. Afterwards, there's live music in the lounge — the perfect spot to hear plenty of fish tales.
- The Weekend: Relive a bygone era in Boca Grande. On the tip of Gasparilla Island on Florida’s southwest coast sits Boca Grande, a tiny town with an adorable main street, a gracious historic inn and a vibe that recalls a quieter, slower time.
Start Here: Back in the Gilded Age, the upscale Gasparilla Inn & Club hosted names like Ford and Vanderbilt. Today, the architecturally striking Inn is still the top place to stay in the area. Choose from 63 cushy guest rooms in the main Inn, built in 1913, or opt for one of 17 cottages (10 of which date to 1930) with spacious multi-bedroom set-ups and expansive screened porches — the perfect perch for evening cocktails.
Weekend To Dos:
1. Drive to the island’s southern end to tour the Boca Grande Lighthouse, built in 1890. Not your typical statuesque structure, this one-story lighthouse has a square tower protruding through the center of its hipped roof. Its museum tells the area history; most intriguing is the island’s phosphate operations and the ships that arrived to transport the mineral.
2. Remember the game of croquet? Bring your whites and you too can play on one of the Inn’s three croquet lawns. The Gasparilla Inn Mallet Club has its own clubhouse on the property.
3. For dinner, the Inn’s Main Dining Room, with elegant plantation chairs and monogrammed china, serves New American cuisine, and its wine list is exceptional. As they have been for almost 100 years, men are asked to don jackets for dinner in season (late December through March) — a time-honored touch we love.
- Looking for what to do for Valentine's Day for the perfect couple's retreat? Take a look at our picks for the sexiest hotels and resorts in Florida and start planning your romantic getaway — just the two of you.
- The Weekend: Slow down in Siesta Key. Recharge with a no-rush weekend on the flour-soft beaches of Siesta Key.
Start Here: You’ll find plenty of vacation rentals here, but to make things super-easy try the Hyatt Siesta Key Beach resort—the only luxury hotel property on the six-mile stretch. Instead of traditional hotel rooms, this residence club offers rentals on one- to four-bedroom condo-style units with washer-dryers and kitchen that would make any Food Network chef feel at home. Plentiful chaises, umbrellas, sand toys and paddleboards make it easy to relax oceanside, and the waterfall/hot-tub combo and poolside cabanas will equally spoil you.
1. Complimentary bicycles let you cruise under the banyan trees on Midnight Pass Road at a leisurely pace. Along the way, you can peek into the backyards of some of the region’s most gorgeous beach houses.
2. Go north and peruse 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. (We won’t tell anyone how fast you eat it.)
3. 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, and take your time as you dine, keeping an eye out for dolphin and long-legged waterfowl.
4. No one understands the importance of slowing down more than Southerners, so don’t miss a meal at Owen's Fish Camp restaurant for a home-grown taste of the Gulf with cornmeal-crusted catfish and collard greens.
The Weekend: Stay in downtown Naples. Leave the car keys behind with a weekend in the heart of downtown Naples, where you can people-watch from a balcony fronting Fifth Avenue and take a plunge in the city’s only rooftop pool.
Start Here: Stay at the swanky Mediterranean-inspired Inn on Fifth, a boutique inn nestled in the center of downtown Naples. With a location this good, there’s there’s no need for an advanced itinerary; the best of the city’s chic downtown is within walking distance, including high-end shops and galleries, chef-owned restaurants and even the beach — though you may prefer taking a dip in the rooftop pool instead.
1. On the third floor of the Inn is the Asian-inspired Spa on Fifth, where you can experience the benefits of wine— without taking a sip. The spa’s signature vinotherapy treatments capitalize on the antioxidant and anti-aging benefits of resveratrol and polyphenols, found in grapes, grape seeds and vines.
2. You won't have to walk far to sample Naples' dining scene. The Inn serves up pub food and draft beer at McCabe's Irish Pub & Grill, and fresh seafood at Truluck's Seafood Steak & Crabhouse. But that's just the start: There are more than 37 restaurants nearby, and you'll find one of our favorites, the Café & Bar Lurcat, just a three minute walk away. (Don’t miss their signature cinnamon and sugar mini-doughnuts, served perfectly warm.)
3. Catch a play at the Sugden Community Theatre, which offers year-round performances on Wednesday through Sunday. The venue is just a hop from the inn, so you can walk to one of the nightly shows.
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- Our top-ten lists for getting the most out of the Sunshine State will inspire you to get up and go. Find beaches, bars, boating and more!
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