Vibe | With a population of less than 2,500, this historic fishing village promises a slow pace, miles of unspoiled beaches, and enormous oysters.
Breakfast Joint | Locals start the day at the Apalachicola Riverwalk Cafe, where crab quiche is a favorite. (Editor’s note: This location has closed since the article was printed in 2015.)
Must-See Attraction | Perched on the banks of the Apalachicola River, the Orman House was built in 1838 by one of the town’s leading cotton merchants and showcases a variety of period furniture.
Must-Stop Shop | Stock up on supplies—from outdoor apparel and backpacks to fishing rods and paddle boards—to explore Florida’s Forgotten Coast at Apalach Outfitters.
Grub | A fishermen’s hangout, Papa Joe’s Oyster Bar & Grill specializes in oysters on the half shell, freshly plucked from Apalachicola Bay. (Editor’s note: This location has closed since the article was printed in 2015.)
Watering Hole | Drink a Dirty Blonde brew from locally owned Oyster City Brewing Company, shell some gratis peanuts, and jam to live music at Bowery Station.
Unofficial Mayor | Captain Gil Autrey of Captain Gil’s River Cruises is known for his witty commentary and his knack for finding the area’s elusive gators.
Vibe | Though it’s best known for its resort casinos and attending nightlife, this former French settlement is also prized for its arts community and its shrimping industry, the biggest on the Gulf.
Breakfast Joint | You can’t go wrong with the shrimp and grits in a Cajun cream sauce at Fisherman’s Wharf–style McElroy’s HarborHouse.
Favorite Pastime | Admire architect Frank Gehry’s jaw-dropping campus and view the works of master potter George Ohr at the Ohr-O’Keefe Museum of Art.
Must-See Attraction | The tip of the Lighthouse Pier is the perfect spot to see both spectacular sunrises (after a long night at the tables) and glowing sunsets.
Must-Stop Shop | Stand in the thirty-two-foot-tall jaws framing the entrance of Sharkheads before shopping for souvenirs and house-made saltwater taffy.
Grub | The oldest family-run seafood market on the Gulf, Desporte & Sons Seafood Market & Deli offers a popular daily fish special, which includes gumbo, fries, and a drink for $6.95.
Watering Hole | Pull in at Ole Biloxi Fillin’ Station for a cold beer or auto-themed cocktail (Pink Cadillac, Mustang Sally). Top off your tank with a plate of crawfish nachos.
Unofficial Mayor | Owner of iconic Mary Mahoney’s Old French House, Bobby Mahoney is known locally as a bit of a comedian. See his “show” tableside as a patron of the restaurant.
Vibe | Averaging 361 days of sunshine a year, this barrier-island city draws families with its easy accessibility and wide variety of accommodations and attractions.
Breakfast | Joint Kids nosh on chocolate-chip pancakes and Froot Loops while parents sip well-made Bloody Marys at Clear Sky Beachside Cafe.
Favorite Pastime | Comb thirty-five miles of beaches in search of prickly cockles, Florida horse conchs, and Sunray Venus shells.
Must-See Attraction | Spotting a dolphin is guaranteed on the Little Toot Dolphin Cruise. The shimmering sea mammals love to play in the wide wake created by the tug.
Must-Stop Shop | Every night is a cause for celebration at Sunsets at Pier 60, where local artists and jewelers sell their wares along the 1,080-foot pier.
Grub | For a waterside meal that doesn’t break the bank, Frenchy’s Rockaway Grill’s grouper sandwich ($10.95) hits the spot, not the wallet.
Watering Hole | Do as locals have since 1926, and sidle up to the bar at Palm Pavilion for rum runners and pina coladas. Watch out for kiddos playing in the sand.
Unofficial Mayor | Winter the Dolphin’s injury, recovery, and prosthetic tail inspired The Dolphin Tale movies. See her in person at Clearwater Marina Aquarium.
Vibe | These twin cities form a quintessential beach community that’s home to acclaimed seafood shacks, a world-famous cocktail lounge, and the biggest Ferris wheel on the Gulf.
Breakfast Joint | Koastal Toast (French toast made with thick slabs of Texas toast) and golden hash browns are served all day at popular Kitty’s Kafe.
Favorite Pastime | Fish from the second-longest pier on the Gulf, walk eighteen miles of trails, or attempt the seven-tower zipline course at Gulf State Park.
Must-See Attraction | Climb to the top of historic Fort Morgan to see where Union Admiral David Farragut gave the command, “Damn the torpedoes. Full speed ahead!” during the 1864 Battle of Mobile Bay.
Must-Stop Shop | Score a one-of-a-kind souvenir at the Coastal Arts Center of Orange Beach, where glass blowers, potters, and painters create and sell their work.
Grub | Flip-flops are as fancy as anyone gets at Doc’s Seafood Shack & Oyster Bar, a popular dive where the fried shrimp come straight from the waters outside the door.
Watering Hole | Ride the line at the legendary Flora-Bama, known for its musical chops (Jimmy Buffett plays impromptu jam sessions) and its version of the iconic Bushwacker frozen cocktail.
Unofficial Mayor | Lucy Buffett, sister of “Margaritaville” singer Jimmy, is a local celebrity in her own right, serving as proprietress of popular Lulu’s restaurant at Homeport Marina.
Vibe | A gateway to Louisiana’s Gulf coast, this bayou town is renowned for its outdoor recreation and convivial brand of zydeco-fueled Southern hospitality.
Breakfast Joint | Rub elbows with locals at Demitasse Cafe, where you can fuel up on a shrimp omelette and chicory coffee.
Favorite Pastime | Year-round open seasons, liberal limits, and more than fifty charters make the city a mecca for bow, deep-sea, swamp, and fly-fishing.
Must-See Attraction | For a close encounter with the unofficial mascot of bayou country, visit Greenwood Gator Farm, where you’ll find reptiles ranging from hatchlings to twelve-footers.
Must-Stop Shop | Get your fishing essentials (tackle, bait, ice, beer) and check out the antiques at Cecil Lapeyrouse Grocery, a century-old, family-run general store.
Grub | Tuck into slow-cooked etouffee, gumbo, and fresh Cajun Gulf seafood at A-Bear’s Cafe. Save room for the legendary peanut butter pie.
Watering Hole | Laissez les bons temps roulez at The Jolly Inn Cajun Dancehall, where owner Werlien Prosperie serves up drinks and classic Cajun music.
Unofficial Mayor | Captain Wendy Billiot (aka “Bayou Woman”), operator of eco-tour company Wetland Tours and Guide Services, is known for her near-encyclopedic knowledge of the area.
Vibe | With its world-class spas, shopping, and golf, this southwest Florida city offers the ultimate in luxe living.
Breakfast Joint | Blueberry’s comes by its “Pancake Factory” nickname honestly, as it cranks out a dozen varieties—from blueberry (of course) to bacon—every morning.
Favorite Pastime | Play the spectacular 36-hole, Greg Norman–designed Tiburon course at The Ritz-Carlton Golf Resort, Naples.
Must-See Attraction | Calling all bird watchers! Spot bald eagles, ospreys, migratory shore birds, and owls at Delnor-Wiggins Pass State Park.
Must-Stop Shop | Shopping in Naples can almost be considered a sport, and Waterside Shops is a favorite venue, with more than sixty retailers including Hermès, Louis Vuitton, and Gucci.
Grub | Indulge in a two-, three-, or four-course dinner (your choice) waterside at Mereday’s Fine Dining; the tasting menu changes daily. (Editor’s note: This location has closed since the article was printed in 2015.)
Watering Hole | Sidle up to the bar at The Continental for a sophisticated cocktail (try the Hemingway Once Said) and an equally highbrow snack of caviar parfait with egg salad and brioche.
Unofficial Mayor | Bob Smith is often spotted driving his white 1962 MGA convertible roadster with an unconventional passenger: “Camille,” a costume camel head bedecked in sunglasses and a mink stole.
Vibe | Perfectly quaint, this planned beachside town off Scenic Highway 30A is the ideal spot for a getaway a deux.
Breakfast Joint | The line trailing out the door of Summer Kitchen Cafe is a testament to the delicious sausage frittata made with—you guessed it—rosemary.
Favorite Pastime | Explore the charming town on a bicycle built for two from Bamboo Bicycle Company.
Must-See Attraction | The lovely little Town Hall hosts live music performances, as well as the ultimate romantic expression: weddings.
Must-Stop Shop | Count on plenty of personal service at CK Feed & Supply Provisions & Gifts, whether you’re shopping for snacks or picking up prepared dishes for a romantic dinner at your pied-a-terre.
Grub | Reserve a table on the wrap-around porch at stylish Havana Beach Bar & Grill. Cuban-inspired tuna escabeche and lobster risotto are sourced right from the Gulf.
Watering Hole | Have a seat in the candle-lit lounge at Restaurant Paradis, and turn up the heat with a round of signature Sriracha margaritas.
Unofficial Mayor | Friendly artist, photographer, and unofficial town style director Tommy Crow is a familiar fixture on Main Street, where he has a studio.
Editor’s note: This article was originally published in our Spring/Summer 2015 issue. Since being published, several establishments mentioned in the story have closed.