1. Gourmet Cracker Cooking School, Everglades City

• Best For: Foodie friends. Grab your fave dining partners and just spend a day chopping, sautéing and eating with Terri Rementeria, owner of Camellia Street Grill (239.695.2003), a cool flamingo-pink restaurant tucked deep into Everglades country. When you see her psychedelic-painted Volkswagen bug, you know you've arrived.
• Book It: There's nothing formal about this cooking class, and Rementeria will organize it for groups as small as three, maximum 15.
• The Menu: Sautéed frog legs; alligator seasoned with ginger, cilantro and the chef's signature blend of herbs (you pick them fresh from her garden); Indian flatbread, fried cornmeal-and-flour dough; and Key-lime pie. After preparing the meal, enjoy it on the screened-in patio overlooking the Barron River.
• Sleep: Just down the road is the Ivey House bed-and-breakfast, a 1928 boarding house that's still run as such with common bathrooms, so opt for a two-bedroom cottage.
• Explore: Everglades City is a mile-long mangrove island. And a canoe trip with Everglades Rentals & Eco Adventures through the tangled tunnels of the Everglades' Ten Thousand Islands is the perfect weekend wrap. camellia-street-grill

2. Marco Island

• Best For: Rugged island adventure. What does the Southwest Florida Nature Festival have in common with the annual Mullet Festival at Stan's Idle Hour bar, other than they're both in January and on or near Marco Island? Birds—sort of. The nature fest (Jan. 15-17) at Rookery Bay National Estuarine Research Reserve gives binocular-toting attendees the opportunity to spot Southwest Florida's other winter residents. And Stan's, the Sunday hangout, crowns its buzzard queen Jan. 29-30.
• Insider Tip: Book a field trip hassle-free—backcountry-swamp buggy excursions or a 15- mile bike hike through Shark Valley in the Everglades—at rookerybay.org.
• Sleep: At the Marco Beach Ocean Resort, choose a suite with regal old-world beds, a private Gulf-facing balcony and a full kitchen that the property's concierge will be happy to stock for you.
• Eat: Dress up for dinner at the resort's lavish Sale e Pepe, where chef Alberto Varetto's centuries-old recipes, like veal ravioli and beef tagliata, are prepared with ingredients from his native Torino. stansidlehour.net, marcoresort.com, rookerybay.org

3. The Edge of the Everglades

• Best For: Intrepid anglers. Spend a weekend where the river runs deep—the River of Grass, that is, and make your home base the Caribbean-style Lemon Tree Inn, where the lemonade is always fresh.
• Reason to Stay: Book the inn's "Go Fish" program, a five-hour fishing adventure by kayak into the Everglades backcountry. Guided by Capt. Charles Wright from Everglades Kayak Fishing, you'll have his nearly four decades' worth of Everglades National Park experience at your fingertips. He knows exactly where snook, tarpon, red-fish, speckled trout and Spanish mackerel hide.
• Best Eats: Ride a bicycle into town for fish that you don't have to cook yourself at M Waterfront Grille.
• Sleep: We love each room's original, Caribbean artwork and plantation shutters, but it's the four-poster bed that had us at hello. lemontreeinn.com

4. The Heart of the Everglades

• Best For: Swamp lovers. Photographers Clyde and Niki Butcher know there's only one way to appreciate their Everglades home: full immersion. Pay $75 (includes $50 gallery gift certificate) to plunge thigh-deep into the swamp and discover a new world under a cathedral of cypress trees during the Butchers' biannual Muck-Abouts (Presidents Day and Labor Day weekends). The gracious hosts prefer to stay dry, greeting guests in their Big Cypress Gallery.
• Don't Forget: A waterproof camera and change of clothes. You'll want to stick around for the food, camera demos and Florida folk music.
• Sleep: Yup, it's really in the middle of nowhere, and the closest accommodations are 23 miles away in Everglades City. Rent an authentic Florida stilt apartment at River Wilderness; canoe or fish from the yard; and enjoy the breezes on a screened waterfront porch. Any other weekend, rent the Butchers' cottage homestead.
• Insider Tip: For a tamer—and drier—trek, stick to the boardwalk at nearby Corkscrew Swamp, where a rare ghost orchid blooms from April through August. clydebutcher.com, river-wilderness.com

5. Naples

• Best For: Well-heeled sophisticates. This Gulf Coast city with European flair is for those who like to play with pretty things—whether that's a gorgeous beach, an Old Florida-style golf course at the Naples Beach Hotel & Club or the swanky boutiques of Fifth Avenue and Third Street South.
• Natural Experience: The new Naples Botanical Garden is home to native Floridians like sabal palm, bougainvillea and silver palmetto. Caribbean, Brazilian and Children's gardens round out the displays.
• Stepping Out: Home to the Naples Museum of Art, the Naples Philharmonic Orchestra and even the Miami City Ballet, the Naples Philharmonic Center for the Arts is the perfect place to wrap a day.
• Sleep: The family-owned Naples Beach Hotel & Golf Club is a sprawling resort where you can tour an orchid greenhouse, play tennis or visit the spa. The deck at the on-site HB's on the Gulf is the best spot in town to toast the sunset.
• Off-Season Tip: The SummerJazz concert series lures top talent to the oceanfront green at the Naples Beach Hotel & Golf Club. naplesbeachhotel.com

6. Sanibel Shell Fair & Show, Sanibel Island

• Best For: Seashell collectors. Cross the bridge from Fort Myers and you're on Sanibel Island, a tropical place where seashells abound. Beachcombers who head out at low tide are rewarded with the most interesting finds on the Gulf coast, but if you come during the Sanibel Shell Fair and Show (March 4-6), you can learn the science behind the collecting as you gaze at the eye-candy displays.
• Don't Miss: Artists display sailors' valentines, jewelry, lamps and furniture during the juried scientific and artistic competitions.
• Learn: The Bailey-Matthews Shell Museum tells how the Calusa people turned shells into hammers and fishing tools. It's also home to an interactive shell-classification wheel for easily identifying finds.
• Eat: Romantic views of the Gulf of Mexico pair beautifully with Thistle Lodge's fried whole snapper with roasted-garlic-cilantro mojo.
• Sleep: Sanibel Harbour Resort & Spa is one of just a few tall buildings on the island, so savor a lovely suite on the 11th floor with a sweeping vista of San Carlos Bay. fortmyerssanibel.com

7. Okeechobee Waterway, Fort Myers

• Best For: Backwater views of small-town Florida. BYOB (your own boat, that is) and enjoy a slow ride along this 154-mile scenic waterway, which connects the Gulf of Mexico to the Atlantic and has a surprise in the center: Lake Okeechobee, one of the world's largest inland lakes. Ideal for nature lovers, anglers and peace seekers, the passage drifts east from Fort Myers past time-forgotten towns like LaBelle and Indiantown before rejoining civilization in Stuart.
• Sleep: The historic 1938 Clewiston Inn is the midway point and offers call-ahead pickup service from local marinas as well as Southern-style fried chicken and local catfish. Bonus: Breakfast is included—even the Sunday buffet.
• Pit Stop: Dock at Wahoo's on the Waterfront in Stuart, where the locals love the pear martinis and tuna wasabi. clewistoninn.com

8. Boca Grande

• Best For: Discovering Old Florida at its finest. If you like the casual elegance of fine dining (jackets required), a game of croquet (with players dressed satirically correct) and even a genteelness that seems to elude our pop-culture society, a trip to Gasparilla Island, with a stay at the Gasparilla Inn & Club, would suit you well.
• When to Go: Time your visit for the Gasparilla Inn Food & Wine Weekend (Jan. 15-17). Chefs prepare dishes that pair perfectly with international wines for Friday evening's welcome reception at the beach club.
• Shop: In between Saturday's wine seminars, hop on to one of the resort's golf carts and zip along banyan-canopied streets to the three-block downtown. Pop into Holly's Home Accessories for vintage Florida signs or Boca Grande Outfitters for fly fishing gear.
• Outdoors: Golfing the inn's island course, bicycling along a beach route and reeling in tarpon (April through September) with local fishing guide Capt. Mark Bennett are among the signature activities here.
• Sleep: Whether you choose a cottage with a screened-in porch or a room in the main building, the accommodations are immaculate. Cheery yellow walls provide the backdrop for white-wicker furnishings and hurricane lamps that exude that Old Florida feel. the-gasparilla-inn.com, tarponsnook.com

9. Punta Gorda

• Best For: Gourmets willing to go out of the way. Discover a mix of small-town charm and surprisingly tasty eats at this Gulf-side town that hugs Charlotte Harbor.
• Perfect Day: Shop the Saturday farmers market, stroll the nearby art galleries & studios, and then head to Pies and Plates for cinnamonbun bread pudding and a class on how to make gelato or crab pesto succotash (it doubles as a culinary school).
• Best Eats: Dine along Marion Street, where your choices range from Piemontese burgers at the Tavern to pork prime rib at River City Grill to perfect confit at the Perfect Caper.
• Best Drinks: Grab zinfandel or Veuve Clicquot right off the bottle-clad walls of Bin 82, or hit the 1890s Ice House, now chilling 200 craft drafts and bottles.
• Country Flavor: Hop a hayride tour of Worden Farms' 55 acres of organic bounty. Tours last approximately one hour.
• Sleep: Check into the Wyvern, a boutique hotel with river views and more good food at Lulu, the hotel's Nuevo Latino restaurant. thewyvernhotel.com