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Pretend like you own the place on Sea Island in Georgia.

Above: The Cloister at Sea Island  Photo: Courtesy of Sea Island

While it would be easy enough to fly directly to Nashville or Atlanta, hurtling through the air is no substitute for the romance of a long drive toward the ocean. This surprisingly direct route takes you through a string of charming Southern cities. No one would blame you for stopping when you reach the moody and gothic riverfront town of Savannah. But if you press on for 100 more miles, you can dig your toes into the sand of Georgia’s southeastern coast on a bit of land surrounded by five miles of spectacular shoreline.

The boring part of the journey happens on an uneventful stretch of I-65 in Indiana. Turn on an audiobook, and before you know it, you’ll arrive in Indianapolis three hours later, in time for lunch and a stroll along the canal that runs through downtown.


The South arrives quickly as you roll through Kentucky horse country in the hills surrounding Louisville and approach Tennessee. When you cross the Cumberland River and pull into the neon-blazed streets of Nashville, you’ll get a sense of why Music City has taken on a new moniker of late: Nash Vegas, meant to suggest that the iconic place has evolved into something more creative, daring, and hip. Look for inven- tiveness in unexpected places—a sus- tainable brewery run by two passionate owners, a tiny curated hotel, and an am- bitious new restaurant called Sinema in the Berry Hill neighborhood (say hello to chef Dale Levitski, who recently moved to Nashville from Chicago).

Bright green hills and thickly forested ridges emerge as you drive alongside the Tennessee River. Atlanta is easily the most metropolitan of the cities on the route, but dogwood, oak, and elderberry trees push in everywhere. Stay in Savannah, the next stop, just long enough to absorb its lush antebellum vibe.

Slow down the clock and take the famously scenic Highway 17, which follows Georgia’s inlet-fringed coast, for the final leg to Sea Island, a key-shaped sliver of oceanfront property owned by a consortium that operates the two lavish resorts in the area. To get there from mainland Georgia, cross St. Simons Island, itself a lovely vacation spot, then proceed down a private drive. A massive canopy of live oaks draped in Spanish moss and a salty breeze will greet you.

Committing to a resort vacation on a private isle may require a leap: Will there be enough to do? Sea Island, long a playground for the Southern elite, offers an almost absurd variety of activities. As a guest at the Cloister, a sprawling resort complex, you can learn archery, practice skeet shooting, fine-tune your backhand on the tennis courts, fish for tarpon, or simply indulge in a massage. Test the world-class fairways and greens at the Lodge, the Cloister’s posh sister resort, a short shuttle ride away on St. Simons.

Oh yes, and then there’s the beach. The wide shoreline, loved by loggerhead sea turtles, is your gateway to the surrounding tributaries of a saltwater tidal marsh, alive with creatures including dolphins, giant horseshoe crabs, and pelicans. You won’t be able to do it all. So at some point, just pull up a chaise and give in.

Where to Stop Along the Way



Chicago → Indianapolis: 183 miles, 3 hours
Eat Spend a breezy evening on the patio at Bluebeard (bluebeardindy.com), named for the Kurt Vonnegut novel and serving an admirable panzanella salad with arugula and Manchego.
Do Meet eight newcomers at the Indianapolis Zoo’s new International Orangutan Center (indianapoliszoo.com), opening Memorial Day weekend. The Children’s Museum of Indianapolis (childrensmuseum.org) hosts your only chance to see China’s life-size terra-cotta warriors in the United States this year (through November 2).
Lodge Slumber in one of 26 Pullman railcar guest rooms at Crowne Plaza at Union Station (ihg.com; rooms from $139).

Nashville, Tennessee

Indianapolis → Nashville: 287 miles, 4 hours
Eat In the booming Berry Hill neighborhood, visit former Chicago chef Dale Levitski (Frog N Snail) at Sinema (2600 Franklin Pike), his new restaurant opening in June inside an old two-story art deco theatre.
Shop Have a pair of custom jeans tailored while you wait at Imogene + Willie (imogeneandwillie.com), a gas station turned denim boutique.
Lodge In the Gulch neighborhood a few blocks from downtown, try one of five king rooms hung with rotating works of art at the nearly hidden Hotel 404 (the404nashville.com/hotel; rooms from $275).
Two hours after leaving Nashville and just before you cross the state border into Georgia, you’ll reach Chattanooga, a cosmopolitan riverside oasis in the Tennessee hills. Stop at TerraMae Appalachian Bistro in the StoneFort Inn (terramaechattanooga.com) for a lunch of deviled eggs, rosemary biscuits, pickled vegetables, and crisp strips of benne seed bacon served upright in a jar. In June, the Hunter Museum of American Art (huntermuseum.org) exhibits works by contemporary artists who live in the South.


Nashville → Atlanta: 246 miles, 3.5 hours
Eat In always-buzzy Buckhead, foodies have declared St. Cecilia (stceciliaatl.com), new this year, Atlanta’s restaurant of the moment (try the seafood pastas).
See Opening June 23, the 42,000-square-foot Center for Civil and Human Rights (cchrpartnership.org)—a museum and activist experience rolled into one—is Atlanta’s biggest new attraction.
Lodge Two blocks from Centennial Olympic Park, the mod 252-room Aloft Hotel (starwoodhotels.com/alofthotels; rooms from $159), opened in April, has a major perk for summer: an outdoor pool.

Savannah, Georgia

Atlanta → Savannah: 248 miles, 3.5 hours
Eat Join locals in a former auto body shop for a rich, artery-clogging Southern breakfast—often with a twist—at the atmospheric J. Christopher’s (jchristophers.com).
Do Delve into some 50,000 new, rare, and used books tucked into every conceivable nook at the Book Lady Bookstore (thebookladybookstore.com). Then visit the childhood home of novelist and Southern literary demigod Flannery O’Connor (flanneryoconnorhome.org).
Lodge Enjoy views of the Savannah River from the rooftop at the modern Bohemian Hotel (bohemianhotelsavannah.com; rooms from $249).

Sea Island, Georgia

Savannah → Sea Island: 87 miles, 1.5 hours
Lodge The Cloister at Sea Island has options for nearly every situation, from large suites to clan-accom- modating beachfront villas. Golf nuts favor the Lodge at Sea Island (seaisland.com for both resorts; rooms from $505). Guests have access to amenities at both.
Eat One day, order a soft-shell crab sandwich on the back patio of River Bar at the Cloister, with views over the Black Banks River. The next, go for oysters and dry-aged beef at Colt & Alison at the Lodge.
Do Sail or kayak down tributaries of Sea Island’s extensive saltwater marsh with guides from the Cloister’s Rainbow Island Water Sports Center. If you play golf only once, pick the Seaside course ($225 for 18 holes) at the Lodge, the site of the PGA Tour’s McGladrey Classic in October.


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