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Your impression of Hilton Head depends on where you stay when you visit the island. The oldest and best known of Hilton Head's developments, Sea Pines, occupies 4,500 thickly wooded acres. It’s not wilderness, however; among the trees are three golf courses, tennis clubs, riding stables, and shopping plazas. A free trolley shuttles visitors around the resort. Other well-known communities are Palmetto Dunes and Port Royal Plantation.
A good destination for families, Driessen Beach Park has a playground, clean shower and restrooms, and a charming path to the beach that’s part boardwalk, part sandy path, part beach matting. It's often peppered with people flying kites, making it colorful and fun. Amenities: lifeguards (seasonal); parking (metered); showers; toilets. Best for: sunrise; surfing; swimming; walking.
In 1996, Old Town Bluffton was designated a National Register Historic District town thanks to the 80-some historic churches and cottages that still stand there today. Originally inhabited by the Yemassee people, who were driven out by the first English settlers, the town's later population of slaveholders played a key role in South Carolina's secession. By the late 1990s, though, Old Bluffton had become the quirky cousin of Hilton Head, with its well-worn bungalows populated by art galleries and antiques shops. Today, historic homes and houses of worship still flank oak-lined streets dripping with Spanish moss, but now they intermingle with newly constructed tin-roofed buildings designed and laid out to preserve the small-town vibe. Anchored by Promenade Street, the modern section hops with trendy bars, restaurants, and shops. Grab a sandwich to go from the Downtown Deli ( 1223 May River Rd.) and head to the Calhoun Street Public Dock for a picnic looking over the May River. (Instagrammers and photographers should aim for sunset.) While there, check out the beautiful grounds of the historic Church of the Cross ( 110 Calhoun St.). To buy fresh shellfish off the dock, visit Bluffton Oyster Company ( 63 Wharf St.) at the end of Wharf Street.
