Literally the prototype of the modern planned resort community, Hilton Head Island is also a case study in how quickly and utterly a landscape can change when enough money is introduced. Once consisting almost entirely of African Americans with deep historic roots in the area, in the mid-1950s Hilton Head began its transformation into an almost all-white, upscale golf, tennis, and shopping mecca populated largely by northern transplants and retirees.

As you can imagine, the flavor here is now quite different from surrounding areas of the Lowcountry, to say the least, with an emphasis on material excellence, top prices, get-it-done-yesterday punctuality, and the attendant aggressive traffic.

Giving credit where it’s due, however, Hilton Head knows what its target audience is and delivers the goods in a thoroughly professional manner. While it’s easy to dismiss it as a sort of Disney World for the elite—a disjointed collection of gated communities comprising 70 percent of its area—the truth is that millions of visitors, not all of them elite by any stretch, not only enjoy what Hilton Head has to offer, they swear by it, returning year after year.

The attraction is quality, whether in the stunning beaches, outstanding cultural offerings, plush accommodations, attentive service, or copious merchandise. The intentional elimination of risk is also part of the island’s appeal, both to the senior demographic as well as the family segment. You won’t see any litter during your stay, and you’re very unlikely to experience any crime. Certainly that’s to Hilton Head’s credit and no small reason for its continued success.

One of the great unsung positive aspects of modern Hilton Head is its dedication to sustainable living. With the support of voters, the town routinely buys large tracts of land to preserve as open space. Seemingly every hundred yards or so, you’ll come across a sign indicating how many acres have been preserved in the immediate area.

Hilton Head was the first municipality in the country to mandate the burying of all power lines, and one of the first to regularly use covenants and deed restrictions. All new development must conform to rigid guidelines on setbacks and tree canopy. It has one of the most comprehensive signage ordinances in the country as well, which means no garish commercial displays will disrupt your views of the night sky. If those are “elite” values, then certainly we might do well in making them more mainstream.

Just outside Hilton Head are two of the Lowcountry’s true gems, Bluffton and Daufuskie Island. While Bluffton’s outskirts have been taken over by the same gated community sprawl spreading throughout the coast, at its core is a delightfully charming little community on the quiet May River, now called Old Bluffton, where you’d swear you just entered a time warp. Daufuskie Island, though home to a top-flight golf resort, still maintains much of its age-old isolated, timeless personality, and the island—still accessible by boat only—is still one of the spiritual centers of the Gullah culture and lifestyle.

Getting to Hilton Head Island

A few years back, the Savannah International Airport added Hilton Head to its name specifically to identify itself with that lucrative market. It’s been a success, and that facility remains the closest airport to Hilton Head Island and Bluffton. From the airport go north on I-95 into South Carolina, and take exit 8 onto U.S. 278 east.

If you’re entering the area by car, the best route is also exit 8 off of I-95 onto U.S. 278, which takes you by Bluffton and right into Hilton Head. Near Bluffton, U.S. 278 is called Fording Island Road, and on Hilton Head proper it becomes the William Hilton Parkway business route. Technically, U.S. 278 turns into the new Cross Island Parkway, but when most locals say “278” they’re almost always referring to the William Hilton Parkway.