Island Dreaming: Twenty Southern Escapes

Fisherman’s Paradise
Chokoloskee Island
Florida

The nearly 150-acre Chokoloskee lies atop an ancient Calusa Indian midden of oyster shells. With maybe four hundred residents at its highest tide, it has neither nightlife nor shopping malls (though do visit Smallwood Store, a onetime trading outpost established in 1906 and now a museum). What the island offers in spades is prime access to some of the world’s best inshore saltwater fishing. Seconds from the dock is the Everglades’ wondrous labyrinth of mangroves and oyster beds, which teem with snook, redfish, trout, and the king of them all, tarpon.

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Where the Ponies Play
Assateague Island
Virginia

The Eastern Shore village Chincoteague gets all the fanfare for its annual July “pony swim” that rounds up local wild horses. Any other time, cross the next bridge to Assateague Island to experience where the herd lives and cavorts among pine groves, salt marshes, and sand. Winding trails offer scenic views, or for a chance to encounter wild steeds at water’s edge, hop a pontoon tour with a local captain. Better yet, paddle over in a kayak.

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Yucatán Hideout
Isla Holbox
Mexico

Isla Holbox may be the best place on the planet to walk barefoot on a summer day. Floating north over Mexico’s Yucatán Peninsula, this car-free hideaway lures roamers with its marshmallow sand and shell-strewn beaches. When you step off the ferry from Chiquilá, about forty miles from Cancún, a faraway feeling rushes over like a tide. Hop a boat to snorkel with migrating whale sharks, or unwind beneath thatched palapas before strolling the sandy streets. Stop for fresh ceviche, ice-cold beer, and pizza topped with tender lobster.

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Small-Town Sanctuary
Dauphin Island
Alabama

Whether you arrive by ferry or the three-mile bridge that straddles Mississippi Sound and Mobile Bay, Dauphin Island slips you back in time, charming visitors with its Mayberry vibes. That is, if Mayberry had an Audubon bird sanctuary hosting hundreds of species viewable from a meandering boardwalk. And seafood shacks serving up the bounty of surrounding Gulf waters. Oh, and miles of beaches. The barrier island is known as the sunset capital of Alabama, and when you’re taking in the glorious views of the horizon from its narrow western end, it’s hard to argue.

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Venture North
Monhegan Island
Maine

It can’t be said for certain if the Virginia colonist and explorer John Smith sailed here in 1614 to escape the South’s steam-bath summers. Not a bad idea, though. Blessed with stirring sea-meets-cliffs scenery, Monhegan is still rustic (no streetlights), but the last four centuries have brought some amenities. Pair fresh-caught lobster with craft beer from tiny Monhegan Brewing Company, for instance. The summertime artists’ colony offers casual studio visits. Requisite lighthouse? Yep. But the most picturesque structure is the 1816 Island Inn, with a wide front porch so inviting it makes even castaway Southerners feel at home.

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Gullah Time Capsule
Sandy Island
South Carolina

Ten miles from the miniature-golf kingdom of Garden City Beach lies another world entirely. Nestled between the tea-colored Waccamaw and Great Pee Dee Rivers behind Brookgreen Gardens, Sandy Island is home to one of the South’s most intact longleaf pine forests, as well as black bears, pitcher plants, and endangered red-cockaded woodpeckers. The bulk of the island’s twelve thousand acres is managed as a nature preserve with day use allowed (access by boat or kayak), while at the south end lies a tiny historic African American community called Mount Rena, whose children still ride a ferry to school. Book a trip with local Rommy Pyatt’s Tours de Sandy Island to learn about island history from slavery to the present, visit the New Bethel Baptist Church (established 1880), and drive through the island’s primeval sandhill forests.

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Island Ghosts
Portsmouth Island
North Carolina

On this remote, boat-access-only northernmost island of Cape Lookout National Seashore, sandy trails wind through ancient dunes, endless marsh, and the remarkable ghost town of Portsmouth Village. Home to nearly seven hundred souls in 1860, it has been long abandoned and is now managed as a historic site. A walking tour takes in century-old cottages scattered among the dunes, an 1840 post office, and the 1894 U.S. Life-Saving station. It’s wild country, so pack water, bug dope, and a sense of adventure.

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String of Pearls
The Virginia Coast Reserve
Virginia

Fourteen undeveloped barrier and marsh islands make up an astonishing archipelago at the southern end of the Delmarva Peninsula, the longest expanse of coastal wilderness on the East Coast. Day visitors are allowed on most of the islands, which the Nature Conservancy owns and manages. The few hardy surf anglers and birders who make it to these shores are treated to a wild coastline that greeted some of the earliest European explorers—and welcomes more than 250 species of birds each year.

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Story-Worthy
Bald Head Island
North Carolina

On the one hand, Bald Head is a private enclave of magnificent beachfront manors, a twelve-thousand-acre retreat with a stunning golf course, a marina, and a spa, with ten thousand acres locked up as an untouched nature preserve. On the other hand, there’s plenty of opportunity to rent cottages and townhomes and act as if you own the place. The island and its Cape Fear marshes inspired the beloved writer Robert Ruark—his grandfather lived in Southport, the jumping-off spot for Bald Head—and his summers here influenced his masterpiece, The Old Man and the Boy.

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Relax like a Rockefeller
The Golden Isles
Georgia

On Jekyll Island, the southernmost of this foursome of barrier islands off Brunswick, Georgia, the Jekyll Island Club Resort stands as a living monument to the region’s extravagant history. The onetime hunting club for the Rockefeller, Vanderbilt, and Pulitzer families underwent a $25 million renovation last year, adding a new beachfront hotel and an open-air riverfront restaurant, and sprucing up the property’s circa-1886 clubhouse. North across the sound sits St. Simons Island, where dry-rubbed ribs at Southern Soul Barbeque, plate-sized T-bones at Bennie’s Red Barn, and stacks of blueberry pancakes at Palmer’s Village Café feed sun-tired vacationers. Cross the causeway to Sea Island, which harbors the five-star Cloister resort, offering falconry lessons, tee times on its three golf courses, and hours of poolside lazing at the Beach Club. The wildest of the bunch is Little St. Simons, home to a lodge with five secluded cottages and thousands of acres of tidal marshlands to explore.

Crystal-Clear Departure
The Exumas
Bahamas

Who needs a swimming pool when you’re in the Exumas? The water surrounding this group of 365 Bahamian islands is every bit as calm and clear. Plus, it hosts giant sea turtles and a famous drove of swimming pigs. Land at the airport on Great Exuma before exploring by car (drive on the left!) or boating to some of the small cays—many of the islands have zero or single-digit populations, and their sandy shorelines make ideal spots for anchoring up, wading the turquoise shallows, and picnicking in perfect privacy.

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Beacon of Light
Hunting Island
South Carolina

After climbing the 167 winding steps of the Hunting Island lighthouse, stop and take in the view: miles of beach bordering rambling trails and campgrounds tucked into maritime forests. Built in 1859—and rebuilt in 1875 after it was destroyed in the Civil War—the only publicly accessible lighthouse in the state has seen Hunting Island transform from an elite nineteenth-century hunting preserve to a beloved South Carolina state park. From Hunting, you can catch a ferry with Coastal Expeditions to roam the rugged trails and untouched beaches of nearby St. Phillips Island, until recently a private retreat for billionaire conservationist Ted Turner and a haven for fox squirrels, loggerheads, and painted buntings.

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A Day at the Edge
Grand Isle
Louisiana

A morning’s drive over swamp from New Orleans, at the place where the continent finally gives way to the Gulf, a sign warns: No Diving From Pier. Below, flounder glide in shallow water. A century ago, before hurricanes scoured the grand hotel and live oaks from Grand Isle, Kate Chopin’s tragic heroine Edna Pontellier swam into infinity from this very beach. But not all is existential on the barrier island: Spend days hunting shells while dorsal fins slip along the uninhabited shore, or fish the interior marsh from a stand of Baccharis. Be at one with the roseate spoonbill, the lurking alligator, the osprey perched on the top of a regal tree.

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The Stargazer’s Dream
The Dry Tortugas
Florida

Seventy miles from Key West, Dry Tortugas is one of the country’s most remote national parks, and spending a night sleeping mere yards from its Civil War–era Fort Jefferson is unforgettable. A ferry drops off a maximum of ten intrepid campers each day, and they schlep in their own fresh water. Primitive? Sure. But having a sprawling historic monument, spun-sugar beaches, and a pristine night sky almost entirely to yourself is worth a little sacrifice.

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Foodie Island
St. Croix
U.S. Virgin Islands

On St. Croix, the pepper and citrus dishes associated with the wider Caribbean region mingle with a long history of culinary traditions brought to the West Indies island.  Dishes like conch callaloo, potato stuffing, crab rice, pickled pork stews, and saltfish blend Spanish Creole and Danish cooking with the island’s flavors. “Even though we’re a port, our food focuses on all these incredible local ingredients,” says chef Digby Stridiron, a native Crucian who cooked in kitchens in New York and Charleston before returning home to St. Croix. “Conch, lobsters, guava berries, yucca flowers, wild roots. I love walking through the farmers’ market.” Stridiron runs four restaurants across the island: Braata, which serves traditional West Indian dishes; Ama at Cane Bay, which touts sustainable seafood; Breakers Roar, a Jamaican Chinese tiki bar; and Caroline’s, his just-opened breakfast spot.

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A Beach Lover’s Eden
Bermuda

It’s no secret that plenty of pleasures await on this hook-shaped archipelago, whether you fancy a refreshing rum swizzle, a scuba dive to shipwrecks along its treacherous reefs, shopping for formal shorts in Hamilton, or taking a bike tour of St. George’s, the oldest continuously inhabited English town in the New World. You could also easily spend the entirety of your getaway hopping among Bermuda’s twenty-plus beaches. Horseshoe Bay, with its rocky outcroppings and hidden nooks, lives up to its ranking among the world’s best, but you’ll want to explore more secluded stretches, too, from the East End’s Cooper’s Island Nature Reserve to Jobson’s Cove on the South Shore. Lounging on any of those famously pink sands, watching the turquoise waves crash hypnotically against majestic limestone bluffs, you’ll achieve a calm you thought impossible outside of Savasana.

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Find Your Flock
Mustang Island
Texas

Of the handful of barrier islands that hug the Texas coast, Mustang Island is the undisputed oasis for outdoors lovers, luring beachcombers, anglers, and birders. The Port Aransas shoreline transforms during Texas SandFest—usually in the spring and this year rescheduled for October—the largest native-sand sculpture competition in the country. Cast back to the island’s sportfishing heyday at the Tarpon Inn, where seven thousand silvery scales line the lobby walls, including one autographed by President Franklin D. Roosevelt. Up the coastline, at the Aransas National Wildlife Refuge, winter brings the bugle calls of the last remaining migratory flock of whooping cranes.

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Old Florida Escape
St. George Island
Florida

Looking for unspoiled Florida these days might seem as quixotic as Ponce de León’s search for the fountain of youth. But there are still a few places—like St. George—left. The twenty-eight-mile-long Gulf Coast barrier island, near Apalachicola, is inhabited but unsullied by high-rises and hordes, with uncrowded white-sand beaches, native sea oats and slash pines, a gorgeous state park, and a laid-back open-air bar with water views (Paddy’s Raw Bar) to round it all out.

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Deeply Rooted
Barbados

Walking beside pastel-painted houses and beneath flowering crape myrtle and pink oleander, Southerners visiting the onetime British colony of Barbados might feel like they’re in Charleston, South Carolina—and for good reason. Many families (including the Middletons and Draytons) took part in the histories of each place, and the architecture and flora still maintain a long-distance relationship. Take in the colonial mansions in the port capital of Bridgetown, or visit Hunte’s Gardens, a twenty-five-minute drive into the island’s heart, where paths meander into a lush valley of ferns, palms, and orchids.

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Tiny Island, Big Party
Harbour Island
Bahamas

There’s no shortage of laid-back merriment to be had on three-and-a-half-mile-long Harbour Island, a sparkle of pink sand just north of Eleuthera. It could be a solo celebration, with a rum-heavy Goombay Smash in hand, at the chic beachside Dunmore hotel. Perhaps it’s a party for two, crooning “Islands in the Stream” at Daddy D’s Nightclub, which turns into a karaoke bar every Tuesday. Or grab a few friends and charter a boat with proprietor Devon “Daddy D” Sawyer himself, who’s just as good a fishing guide as he is a host. 

By C. Morgan Babst, Monte Burke, Gray Chapman, Chris Dixon, Allison W. Entrekin, Amanda Heckert, Sallie Lewis Longoria, CJ Lotz, T. Edward Nickens, Steve Russell, and Caroline Sanders

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This article appears in the June/July 2020 issue of  Garden & Gun. Start your subscription here or give a gift subscription here.