Celebrate Good Times: Southern destinations perfect for marking life’s milestones and special occasions

After a year of cancelled plans, missed holidays, and Zoom toasts, it’s time to dream big again (well, almost).

Jennifer Rainey Marquez

October 12, 2021

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Sunset on the dock at the Moorings Village in Islamorada, Florida

Remember the big trip? The months-in-the-making, counting-down-the-days vacation to mark a special birthday, a friend’s engagement, a graduation, a new addition? After a year of cancelled plans, missed holidays, and Zoom toasts, it’s time to dream big again (well, almost). If congratulations are in order, these Southern destinations offer the perfect setting to celebrate (or do over!) life’s milestones and special occasions.

One for the Ages

40th Birthday
Palmetto Bluff • Bluffton, South Carolina

Nature, but make it luxurious. Is there any better way to greet a new decade than waking up to gorgeous blue skies and a massage appointment booked for the afternoon? Nestled in the South Carolina Lowcountry between Savannah and Hilton Head, Palmetto Bluff is thick with serene salt marshes, century-old live oaks, and wildlife-filled lagoons. Sink into bucolic bliss at Montage Palmetto Bluff, a secluded 20,000-acre resort community where most of the land is a protected nature reserve, complete with an on-site archaeologist. (The area has a rich ecological and agricultural history, and staff have discovered artifacts dating back thousands of years.) Reserve a room at the inn (it’s more like a grand mansion), or book one of the spacious cottages or vacation homes with touches like screened-in porches and vaulted ceilings.

Guests can have their pick of activities, from teeing up at a Jack Nicklaus signature golf course to kayaking the May River (check out the “sandbar,” a tiny island that only appears at low tide). Or just stroll or pedal through the heavenly grounds, which are crisscrossed with walking and biking trails connecting the resort’s two villages, where you’ll find plenty of dining and shopping. (Bring your binoculars; spotting dolphins, alligators, wild turkeys, or other wildlife is virtually guaranteed.) At the world-class Spa Montage, therapists will release any last bit of “big 4-0” tension. Later, load up on local oysters and other coastal fare at the river-to-table Canoe Club, then hit the Octagon Bar for a glass of its signature (and legendarily boozy) Artillery Punch. End the big day with s’mores by the firepit—because even 40-year-olds deserve to feel like a kid sometimes.

“From start to finish, the Montage Palmetto Bluff was the perfect destination for celebrating my friend’s 40th. There were so many experiences to love: boating on the May River, a friendly pickleball competition, relaxing at the poolside cabana with a spicy margarita in hand, and even just hopping on a bike to explore the shops. Don’t miss dinner at Cole’s; our group consumed more buckets of the delicious fried chicken than I’d like to admit.”
—Shauna Achey, Atlanta

70th Birthday
The Greenbrier • Sulfur Springs, West Virginia

The Greenbrier is known as “America’s Resort” for a reason. Twenty-six presidents have stayed here over its nearly 250-year history, and the genteel vibe, stellar service, and colorful Dorothy Draper interiors make for a time-honored experience. Enjoy a low-key weekend with pool time, a spa visit, and complimentary afternoon tea, or choose from the endless activities, including golf, tennis, bowling—even gambling at the casino.

Sweet 16
Orange Beach, Alabama

Start the trip with a perfect beach day amid warm Gulf waters and soft, sugary sand, then lure your family away for some fun: go-kart racing at the Track in nearby Gulf Shores, a 60-foot waterslide at Waterville USA (adults may prefer to kick back on the lazy river), or a Ferris wheel ride and movie night at the Wharf, the town’s 222-acre entertainment district.

That’s What Friends Are For

Bachelor Party
Kentucky Bourbon Trail

Kentucky has always been synonymous with bourbon—after all, 95 percent of the stuff is produced in the state. But this bachelor party isn’t just about distillery tours and tastings. (All those oak barrels and copper stills can blur together after a while.) It’s also about hitting the open road with friends—cruising past verdant rolling hills, mist-topped rivers, and sweeping horse farms. So savor the backroads as much as you would a glass of Pappy: windows rolled down, playlist cranked up. (Tip: To really enjoy this booze-soaked journey, you won’t want to be behind the wheel. Hire a driver or book a chauffeured tour through a company like Pegasus.)

Download a map from kybourbontrail.com to plan your itinerary—and don’t overlook the smaller outfits. The Bourbon Trail also includes 19 small-batch craft distilleries like Willet, whose master distiller, Drew Kulsveen, was a 2020 James Beard Award finalist. Kick things off in Louisville, home to six distilleries and a 30-minute drive from two Holy Grail stops: Jim Beam and Bulleit. For large groups, an Airbnb is often easier (and more cost-effective), but smaller parties may prefer to book at Hotel Distil, which offers in-room bourbon carts and views of historic Whiskey Row, the block-long stretch of buildings that was home to the city’s bourbon industry during the 19th century. At night, hit the Urban Bourbon Trail, which includes 20 bars and restaurants featuring some of the city’s most extensive drink menus.

From Louisville, two main trails extend east (toward Lexington) or south (toward Bardstown). Consider spending a night in Lexington, which offers easy access to nearby big-name distilleries like Woodford Reserve and Four Roses along with a growing dining and nightlife scene. Raise a glass to the groom at Bluegrass Tavern, a bar renowned for housing the largest bourbon collection in all of Kentucky.

“This was not your standard bachelor party trip, and we found a lot to enjoy as bourbon fans and history fans. The distillery guides are extremely knowledgeable, and each offers something different. One of our favorite experiences was trying to discern the flavors imparted by different types of wood barrels at Woodford Reserve, where you can actually purchase your own barrel (for a hefty price). One tip: All of the distilleries require advance reservations, so make sure to book your visits and transportation well in advance. Oh, and don’t miss the country ham and pimiento cheese sandwich at Wallace Station in Versailles.”
—Jesse Drawas, Parkland, Florida

Girlfriend Getaway
Key West, Florida

Nightlife meets nature in this palm-fringed paradise. During the day, cycle around charming neighborhoods, take a snorkel tour of the continent’s only living coral reef, or paddleboard through mangrove forests. After one of the island’s famous sunsets, dig into homemade pasta at Nine One Five before cruising Duval Street to knock back a rum runner (or two).

Couples Trip
Oxford, Mississippi

This quintessential Southern college town is also a dining and cultural hub. You can catch a blues concert at Proud Larry’s; make a pilgrimage to William Faulkner’s home, Rowan Oak; and see Southern folk art at the University of Mississippi Museum. At mealtime, clink glasses at epicurean institutions like City Grocery or Ravine, or bust your buttons on fried chicken and collards at Mama Jo’s Country Cookin.

Family Affairs

Family Reunion
Jekyll Island, Georgia

Just seven miles long and 1.5 miles wide, Jekyll Island is the perfect size for a large family gathering—small enough to keep everyone close by, but big enough to offer a range of attractions and accommodations to suit every age. Once the winter playground of millionaire families like the Rockefellers, Morgans, and Vanderbilts, the island is rich in history. (And hey, if it was good enough for the Rockefellers . . .) Tour the historic district to see how the Gilded Age one-percenters lived—or experience the opulence first-hand by staying at the Victorian-era Jekyll Island Club Resort or a guest suite inside one of the private cottages originally constructed by club members. You’ll also find unspoiled beaches, salt marshes, and maritime forests, thanks to the island’s status as a Georgia state park. Don’t miss a family photo op at Driftwood Beach, a hauntingly gorgeous coastline lined with sea-washed and sun-bleached trees.

Long walks on the beach and century-old buildings too sedate for rambunctious kids or teens? Don’t worry, there’s lots to keep them busy. The island is threaded with more than 20 miles of biking trails, and the terrain is basically flat, so even kids who haven’t outgrown their training wheels can keep up. Visit the Georgia Sea Turtle Center to learn about the endangered loggerheads that lay their eggs here every summer. (You can even join a nightly turtle walk during nesting months.) Or get your adrenaline pumping with an afternoon at Summer Waves Water Park, where the bravest members of your group can shoot through a five-story enclosed waterslide.

“I love how the island is like a small town. Rent a bike to ride the shaded trails, and you might run into someone else from your group as they’re having drinks on a restaurant patio. Nothing’s far away, so you can split off for an hour or two and it’s easy to meet back up. One of my favorite things to do is visit Faith Chapel, which was built for the original members of the Jekyll Island Club. This year is the 100th anniversary of the installation of the church’s Tiffany stained glass window.”
—Peggy Orndoff, Fruit Cove, Florida

Multigenerational/Mother-Daughter Trip
Asheville, North Carolina

Spoil your mom—and yourself—with a weekend in this hip, artsy town with peerless mountain views and a dining scene to match. From Plant’s superlative vegan dishes to Indian street food at Chai Pani to the best farm-to-table fare at Rhubarb (chef John Fleer is a five-time James Beard Award finalist), there’s a menu for every palate. Head south to explore the magnificent Biltmore, a 250-room stunner that remains the largest private residence built in America.

Traditional Family Vacation
Williamsburg, Virginia

Colonial Williamsburg, the nation’s largest living history museum, is a bucket-list trip for many families. Don’t miss the Benjamin Powell House, where kids can learn about the lives of local children 250 years ago. When you’re ready to leave the 18th century behind, head to Busch Gardens for a blast of amusement-park action.

In the Name of Love

Babymoon
Islamorada, Florida

Yoga on the beach. Sunset cruises. Fresh-caught seafood. Parents-to-be deserve a little romance and some serious R & R, and you’ll find it all in Islamorada. This stretch of six sun-soaked islands, about halfway between Miami and Key West, is known for its Edenic landscape—often a backdrop for major fashion photo shoots—and serious sportfishing. It’s also among the most peaceful spots in the Florida Keys.

The Moorings Village, a series of white clapboard cottages and villas set on a lushly landscaped former coconut plantation, offers secluded comfort and million-dollar ocean views—with a generous sweep of private beach. For pampering and couples-friendly fun, opt for the Cheeca Lodge & Spa, which underwent a $25 million renovation in 2018. There, you can snorkel among darting tropical fish, peer into the sparkling blue Gulf from a clear-bottom kayak, or sink a line off the 525-foot fishing pier. If angling isn’t your thing, head to Robbie’s of Islamorada, an unassuming plywood establishment where—for just a few dollars—you can hand-feed minnows to six-foot-long tarpon fish that leap out of the water to grab the bait.

Head across the street from the resort to dine on the local catch at Pierre’s, where celebs like J.Lo have spent date nights luxuriating in the romantic tropical-chic atmosphere. Or spend a few hours browsing some of Islamorada’s many art galleries for a special piece to commemorate your new addition.

“After passing through Islamorada on our first trip to the Florida Keys, we knew it would be the perfect spot to enjoy our final weeks as a family of three. One of our favorite memories was dinner at Lorelei Restaurant, where our one-year-old son, Atlas, had fish for the first time. Let’s just say he now knows the best of the best. We always love relaxing on the beach and watching the sunsets, and on Islamorada you get an incredible view every night. Now we can’t wait to come back as a family of four.”
—Adam Lukaszewicz, Milwaukee

Anniversary Trip
The Greystone Inn • Lake Toxaway, North Carolina

Built on the banks of the largest private lake in North Carolina and surrounded by the Pisgah and Nantahala national forests, the historic Greystone Inn (constructed in 1915 as a private residence) features all the modern comforts—feather-top king beds, exceptional dining, a spa—amidst breathtaking scenery. Go for a day hike (the county boasts 250 waterfalls!) or cruise around the lake in Miss Lucy, the resort’s mahogany electric boat.

Solo Sojourn
Hot Springs, Arkansas

Hot Springs National Park, which celebrates its centennial this year, is home to 47 natural springs that bubble up at a toasty 143 degrees. Pamper yourself by booking a spa treatment at the Buckstaff Bathhouse, which has been offering massages and thermal soaks since 1912. Then spend an afternoon browsing small galleries, boutiques, and antique shops in downtown Hot Springs, considered one of the country’s best art towns.

Fruits of Your Labor

Retirement Celebration
Blackberry Farm • Walland, Tennessee

Yes, there are rocking chairs at Blackberry Farm. But the 4,200-acre resort, tucked into the foothills of the Great Smoky Mountains, offers much more than your grandmother’s idea of low-key leisure (though you could do worse than relaxing for an hour or two amid the purple-wreathed peaks). This opulent country hideaway is also a true working farm—home to an on-site creamery, bakery, brewery, and butchery—and one of the world’s major destinations for dirt-to-table fine dining. The resort’s life-changing meals are included in the room rate, and guests can also opt to roll up their sleeves to prepare a dish alongside one of the chefs or join a sommelier for an extensive wine tasting (there are 160,000 bottles stashed in the wine cellar). Inside an 1870s farmhouse, the Wellhouse spa offers the best in mountain-chic pampering, from the usual massages and facials to guided meditation and private dance instruction.

Blackberry Mountain, a larger sister property located a few miles away, is like an ultra-luxurious summer camp where you can sample an array of potential retirement hobbies. Fire at sporting clays, troll the rivers for smallmouth bass and trout, try your hand at wheel-thrown pottery, or hone your off-roading skills—from behind the wheel of a Lexus GX, with your own personal driving instructor. The Firetower restaurant, set inside a glass-walled 1950s-era lookout tower, offers unbeatable 360-degree views of the mountains. Book a table at sunset to toast your next chapter.

“From the second you pull up the drive, the standard of service surpasses any other place I’ve been. You can go and do absolutely nothing but get a massage, go to the pool, and eat amazing food. But if you’re someone who likes a lot of activity, there is so much to do, and the staff really caters to you and helps make your visit so special. One of my favorite things is just walking through the property—the scenery is stunning. You can chat up the gardener. You can spend time with the truffle dogs. At the spa, you can sit in a beautiful recliner at the end of your treatment and just look over the mountains for hours.”
—Beth Hamilton, Nashville

Graduation Trip
New Orleans, Louisiana

You’ve tossed your cap in the air—now kick up your heels in NOLA, one of the South’s best food towns, where the uniquely bohemian spirit invites every visitor to let loose. Order plates of fried catfish at Barrow’s or steaming dumplings at LUVI (a 2020 James Beard semifinalist), then dance it off along Frenchmen Street, where the sounds of blues and bounce music spill out open doors and across the pavement.

Weekend Reset
Amelia Island, Florida

This northernmost barrier island on Florida’s Atlantic coast is where Southerners come to loaf in style. Hunt for shark teeth at Fort Clinch State Park, pedal under a fragrant forest canopy, or gallop along the shoreline on horseback. Hop over to the historic town of Fernandina Beach for a taste of Old Florida—like a cup of Pirate Punch at the Palace Saloon, Florida’s oldest bar.

This article appears in the Fall/Winter 2021 issue of Southbound.

Celebrate Good Times: Southern destinations perfect for marking life’s milestones and special occasions

One for the Ages

40th Birthday
Palmetto Bluff • Bluffton, South Carolina