St. George Island
Drive time: 1 1/2 hours from Tallahassee
Best for: Those who want to hole up together in a gorgeous house with just a stunning beach and each other for entertainment
The Home: St. George Island is not your typical resort town. There’s not a high-rise hotel or a shopping mall in sight, thank goodness, and it takes a lengthy drive across a four-mile bridge to reach the secluded island. Styles range from two-bedroom cottages with picture-window views of the Gulf of Mexico and Apalachicola Bay to palatial six-bedroom homes with swimming pools and wraparound porches. Opt for a rental home on the west side in the private Plantation community, and you can cruise winding wooded roads and shaded trails through grassy dunes to the jetty at the western tip. On the eastern end of the island, the homes’ main attractions are beachcombing and bicycling to St. George Island State Park, nine miles of pristine, undeveloped shoreline and salt marshes.
Eats: Check out the Beach Pit barbecue joint for slow smoked pork butt and brisket, and seafood specialties like right-off-the-boat Apalachicola Bay oysters and fresh Gulf shrimp.
Explore: Keep an eye out for dolphins, bald eagles and ospreys as you walk your dog on the secluded pet-friendly beaches. During the summer, loggerhead sea turtles come ashore to lay their eggs, and in October migrating monarch butterflies drift across the island. Adventurers can climb the 92 steps to the top of the newly erected Cape St. George Lighthouse for 360-degree views. Stargazing at the night’s pitch-black sky reveals the clearest diamond-studded heaven.
Don’t Miss: For the one day you might just long for civilization, drive to Apalachicola, a nearby historic fishing town. Stroll the streets filled with art galleries, antiques shops and boutiques. Stop at Boss Oyster for a serving of plump Apalachicola oysters that are shucked while you wait.
Book: Collins Vacation Rentals offers modest two-bedroom to luxurious six-bedroom homes. Seasonal rates: $500 to $6,000 weekly.
By Vicky Hodges
Drive time: 2 hours from Miami
Best for: Families or friends in search of island escapism and lots of fishing
The Home: In the Florida Keys, we love the carefree island lifestyle on Islamorada, where flip-flops compete with boat shoes for the “in” footwear and almost everybody owns a vented fishing shirt with a tarpon or bonefish embroidered above the pocket. The island’s moniker, “Sport Fishing Capital of the World,” explains why many of the rental homes have docks and all of them have fishing poles. (But, hey, there’s also plenty of scuba diving and snorkeling.) For friend and family reunions, we picked the four-bedroom oceanside La Playa.
Eats: Stock up on groceries in neighboring Key Largo’s supermarkets on the drive down, or you’ll be visiting the Trading Post market with convenience-store prices. To really feel like an insider, forgo breakfast at home one morning and get the local gossip at Mangrove Mike’s café (mangrovemikes.com) along with a stack of blueberry hot cakes. When the sun goes down, join the locals at Lorelei‘ For authentic Key-lime pie, stop at the new MA’s Fish Camp for Barbara Cockerham’s version—thick graham-cracker crust, tart yellow filling and beautifully peaked meringue.
Adventure: Tucked inside a purple and green beach shack at the Days Inn is A1A Watersports. A WaveRunner trip includes a visit to a sandbar for socializing and a spin past mangrove islands, composed of tangled prop roots, that leads to the Florida Bay, where speedsters get their kicks on more placid waters.
Insider Tip: You can’t visit Islamorada without going fishing. Our pick for a great guide is Capt. Ricky Stanczyk at Bud N’ Mary’s Marina.
Book: Island Villa Properties has oceanfront, bayside or canal properties ranging from flats and condos to townhouses and homes. Seasonal rates: $1,200 to $10,000 weekly.
By Patricia Letakis
Anna Maria Island
Drive time: 1 hour from Tampa
Best for: Those who want to live like beach bums and pretend the rest of the world doesn’t exist
The Home: Renting an adorable cottage or beach house is de rigueur on Anna Maria Island, just south of Tampa. Our favorite is Limefish, from which a sandy path off the back porch leads to the shore. For a more modern sensibility, experience a week in a Frank Lloyd Wright-inspired home set on stilts high above magnificent sand dunes.
Eats: Don’t miss breakfast at Ginny’s and Jane E’s Anna Maria Island Beach Café at the old IGA—a little shop with a café in the back that serves coffee and ridiculously yummy pumpkin bread. For a cool afternoon treat, indulge in homemade ice cream at Two Scoops, opposite the city pier. Dinner is at the Sandbar, a local institution.
Explore: From Beach Bums, rent brightly painted bicycles with baskets on the handlebars or a three-wheel Surrey bike that the whole family can ride on together with the shade of a canopy. Pop into local galleries and boutiques like Sand Dollar, a treasure-trove of sundresses, sandals and nautical-themed home accents. Keep biking till you reach the beaches, where you’ll find tidal pools—perfect for kids to play in—and sandbars—great for bodysurfing. A local favorite is Bean Point on the northwest tip of the island (look for the “Public Access” sign hidden behind the trees). With its wide expanse of white sand and crystal-blue water, you’ll swear you were in the Caribbean.
Don’t Miss: Find a wooden bench at the end of the Rod & Reel Pier overlooking Tampa Bay. The fishing here is great as long as you manage to catch them before the pelicans do. Stroll the weathered pier, made with engraved planks bearing names of local families who helped save the old pier in 2008. Upstairs is the Rod & Reel (941.778.1885) restaurant, which is as Old Florida as it gets. At this authentic fish shack, surrounded by schools of jumping fish and sea gulls circling overhead, the chef serves a memorable plate of fried shrimp.
Book: Pineapplefish (pineapplefish.com) offers everything from small cottages to four-bedroom beachfront homes. Seasonal rates: $1,550 to $4,500 weekly.
By Vicky Hodges
Drive time: 1 hour from Jacksonville
Best for: Those who want a more urban experience peppered with art, history and island fun.
The Home: The Sculptor’s House, the only luxury rental home on the waterfront in historic St. Augustine, was originally owned by Ted Karam, an accomplished sculptor who moved to the Oldest City in 1971 and fell in love with its culture and history. In recent years, his grandnieces Jeanne and Katherine Abboud renovated the home in his memory, filling it with beautiful artwork, an extensive collection of art books, and Karam’s striking wood and bronze sculptures, all of which he crafted on the premises.
Eats: For craft cocktails and farm-to-table cuisine, head to the Ice Plant Bar situated in the city’s historical ice plant factory built in 1927. For your night out, head to the Tasting Room, a contemporary Spanish restaurant that’s tucked back on quaint Cuna Street.
Art Finds: The minute you enter the Sculptor’s House, you’re compelled to find more art, so plan on scouting out the ancient city’s collections. (Join the First Friday Artwalk hosted by the Art Galleries of St. Augustine, and on Saturdays, visit the St. Augustine Amphitheater for a farmers market featuring artists.) Walk a couple of blocks to the downtown, where art galleries pepper the old, brick streets. Don’t miss Nancy Blauer’s colorful, humorous frog paintings at James Coleman Signature Gallery. For some local flair, visit the PASTA Gallery (Professional Artists of St. Augustine), a co-op of more than 20 local artists. End your day at the Lightner Museum, housed in Henry Flagler’s former Hotel Alcazar.
Don’t Miss: Cross the Bridge of Lions to Anastasia Island State Park, between the Atlantic Ocean and Salt Run, a three-mile tidal lagoon. It’s the perfect spot for a windsurfing lesson thanks to the sea breezes. Students can learn from Linda and Jim Craig, owners of Anastasia Water Sports.
Book: Coastal Realty & Property Management has properties ranging from four-bedroom oceanfront condos to one-bedroom coastal cottages. Seasonal rates: $750 to $2,975 weekly.
By Audrey St. Clair