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30 miles NE of Downtown Savannah

The largest sea island between New Jersey and Florida and one of America’s great resort meccas, Hilton Head Island is surrounded by the South Carolina Lowcountry. Palms mingle with live oaks, dogwood, and pines, and everything is draped in Spanish moss. Far more sophisticated and upscale than Myrtle Beach and the Grand Strand, Hilton Head’s “plantations” (as most resort areas here call themselves) offer visitors something of the traditional leisurely lifestyle that’s always held sway here.

Although it covers only 42 square miles (it’s 12 miles long and 5 miles wide at its broadest point), Hilton Head feels spacious, thanks to judicious planning from the beginning of its development in 1952. And that’s a blessing, because about 2.5 million resort guests visit annually (the permanent population is about 35,000). The expansive beaches on its ocean side; sea marshes on the sound; and natural wooded areas of live- and water-oak, pine, bay, and palmetto trees in between have all been carefully preserved amid commercial explosion. This lovely setting attracts artists, writers, musicians, theater groups, and craftspeople. The only city (of sorts) is Harbour Town, at Sea Pines Resort, a Mediterranean-style cluster of shops and restaurants.

The island’s recorded origins go back to visits from Spanish sailors in 1521, and its later “discovery” by an English sea captain, William Hilton, in 1663. By 1860, it boasted 24 plantations, most of them cultivating long-stem Sea Island cotton as well as indigo, rice, and sugar cane. On November 7, 1861, Hilton Head became the scene of the largest naval battle ever fought in American waters. More than 12,000 Union soldiers and marines invaded the island as part of a plan to blockade shipping in and out of nearby Charleston and Savannah. After the Civil War, and with the subsequent destruction of its cotton crops by the boll weevil, Hilton Head slid into obscurity, inhabited mostly by descendants of former slaves, who survived on small farms and as hunters and fishermen. An unusual result of the island’s obscurity involved the survival of their language and culture, Gullah.

In 1956, Charles Fraser, son of one of the families that owned the island, embarked on an ambitious plan to develop it as a modern resort and residential community. Under Fraser, the Sea Pines Plantation (today the Sea Pines Resort) became a much-studied prototype of an ecologically desirable resort community, and was copied worldwide.