11 Southern Beaches and Islands That’ll Have You Dreaming of a Tropical Getaway

This slice of Gulf Coast heaven might as well be a Caribbean escape with Old Florida charm. Clear green-blue waters will wash away any past worries or stress, if at least for the weekend. One of our writers said it best: “This coastal gem maintains a chill vibe, with plenty of telltale signs. Speed limits top out at 35 mph, flip-flops grace bare feet, and there’s a taboo on high-rise buildings  and commercialization. Perhaps one of the greatest draws for weary road trippers? The entire island is accessible by the free trolley that runs daily.”

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If the Keys are off the beaten path already, consider this uncharted territory. Also known as the Village of Islands, this tropical town consists of six tiny islands of the Florida Keys. Besides the coral reef-filled waters and hammock-studded beaches, you’ll find salty-dog charm around every corner. Near the Trading Post, a long-lived pastel market that has been family owned and operated since 1966, discover shops, good eats, and a grassy plaza worth sitting a spell. Along the way, peep streets lined with white clapboard cottages with shutters in tell-tale shades of pastel. Ah, that’s the stuff.

If you’ve never heard of this barrier island off the coast of Georgia, we wouldn’t be surprised. After you learn it was the former playground of Thomas Carnegie (Andrew’s brother) and his wife over a century ago, you’ll be downright jealous. Greyfield, the mansion they built for their daughter, is now an inn with cozy charm and complete with custom daily picnic basket lunches to take out onto the quiet shores, wild horse sightings, and crumbling historic structures—because one more thing: Greyfield Inn is the one and only establishment on the premises. Total serenity. So...have you marked your calendar to buy a future ferry ride ticket over from Fernandina Beach yet? 

The towering palm trees that flank each side as you drive into Alys Beach along Florida’s beloved Highway 30A are almost enough to take you far, far away. And it’s just getting started. The entire town—and by entire, we mean oh-so tiny—looks straight out of Bermuda or Capri, and visitors don’t have to crane their necks to see the ocean from their dinner on the porch at George’s or while on a sunset bike ride with treats from the town’s health hut, Raw & Juicy. Don’t believe us? See for yourself.

How about an Atlantic Coast getaway that feels thousands of miles from hot spots like Myrtle Beach and Charleston, but is actually within driving distance? Pawleys Island is as much known for its low-key flip-flop attitude and handwoven hammocks (from the Original Hammock Shop) as its surfing prowess and quiet beaches. The fact that it is also the hometown of Southerners’ beloved Palmetto Cheese? That’s just the pimientos on top of the spread, in our opinion. The tiny town consisting of upwards 100 full-time residents is the birthplace of the renowned spooky “Gray Man” legend, which means you’ll get yourself a dose of campfire stories, too. 

There’s a lot to love about this classic vacation spot and its neighbor Gulf Shores. Between the powdery sand, blue Gulf waters, fried shrimp, and bushwackers, it hits the coastal sweet spot for family friendly fun. Some favorite seafood joints to lust after until your visit: Doc’s Seafood Shack & Oyster Bar, Tacky Jacks, Mikee’s Seafood, Original Oyster House, The Gulf (order the mojito), or Lucy Buffett’s Lulu’s (ask about The “Pa-Menna” Cheeseburger). While this humble beach town might not strike straight-out-of-the-Caribbean vibes, it sure does make up for it with Alabama sunsets.  

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Since the Florida Keys are as close to the Caribbean as we’re going to get down here in the South, we’ll take full advantage. Marathon is the chosen, albeit unassuming (don’t blink or you’ll miss it!), pitstop for those driving along the Overseas Highway—why? Because just a turn off the road leads you into a secluded world of mangrove labyrinths and pristine beaches as far as the eye can see. Outdoor adventures, such as kayaking and exploring mangrove forests, are easily the biggest draw between bouts spent lazily laying on the sand. 

Our travel editor, Caroline Rogers, offers a hot tip: “It's also home to No Name Pub, a mythic watering hole that's on the outer reaches of most maps. This establishment's walls are covered in thick, decades-old layers of sea salt-crusted dollar bills. Finding No Name Pub requires some searching, so dust off your map-reading skills, because this fabled spot serves a plate of smoked-fish dip that's well worth your effort.”

If your idea of a welcome committee is a herd of wild beach ponies, this windswept coastal paradise will muster quite the wanderlust. The horses have lived there for centuries, which means they’re the real ones in charge and they expect to have the right-of-way. You’re just visiting. The 37-mile-long island straddles the Virginia and Maryland state lines, and Assateague has everything from salt marshes to lush forests to unobstructed Atlantic Ocean views to draw the eye. Take in the breeze at this secluded locale and peep a pony or two while you’re at it.

If you’re the type of getaway goer who daydreams of spending mornings watching fresh citrus being squeezed into juice in front of your eyes and afternoons relaxing by a pool, Vero Beach—a playground for the likes of those who frequent beaches such as Palm Beach and Miami down the coast—just might quench those daydreams. For the real Florida orange juice, head to fourth-generation Schatch Groves. For the pool chair, book a room at Costa d’Este Beach Resort & Spa. Shop and eat local to catch the tiny town’s signature flair in between those tasking commitments. 

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Forget the car—the only traffic you’ll see on this nature-loving island is the occasional golf cart and lots of fat-tire bikes. Accessible only by boat, stepping onto this serene scene is like instantly taking a big breath of fresh salty air. For those looking for a laidback beach adventure, you can rent kayaks and surfboards at the Sail Shop or standup paddleboards from Coastal Urge. Or just visit the Bald Head Island Conservancy to check out some wildlife and enjoy the quiet. It’s your vacation dream; we’re just living in it. 

This beach village comes with an unofficial slogan: "Nice dogs, strange people." And if that isn’t enough to capture your attention, the crystal-clear waters, powdered-sugar beaches, and friendly demeanor of all the locals will get you there. The oldest beach town along Florida’s Scenic Highway 30A, Grayton Beach hasn’t let the urban-planned pastel communities around it change its signature funk. The activity of the day: paddleboarding. The cocktail: a margarita from Chiringo. The dish: crab cakes from The Red Bar. 

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