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