History and the high life come together on an island that knows it’s good-looking
Sullivan’s property values are the highest in the state, thanks to its proximity to Charleston, large lots, and genteel atmosphere (although neighbors like actor Bill Murray keep the mood light). Edgar Allen Poe was stationed here with the U.S. Army in the 1820s, and his legacy remains at the town library and a burger joint named in his honor, as well as at Fort Moultrie, a national monument operated by the U.S. National Park Service. South Carolina’s archetypal state flag has its roots here -- the original fort withstood British cannonballs thanks to the shock-absorbing attribute of palmetto tree logs. From the fort, take in the views of Charleston Harbor and then head to the beach at Station 28.5 (on Sullivan’s, beach blocks are called “stations”) to watch kitesurfers shred in a unique, natural lagoon formed by an offshore sandbar. Sealand Adventure Sports offers lessons if you’re ready to join the wind riders. Station 16 is the starting point for a nature trail that winds through a 200-acre forest before emerging through the dunes onto a peaceful, low-traffic beach.
Know before you go: Sullivan’s has evolved from a barefoot getaway to a wealthy community of second homeowners, and although the beach is public, the rules (and their enforcement) reflect that. Dogs are allowed, but only if you acquire a $50 annual permit at Town Hall. Although alcohol bans are strictly enforced at every beach on this list except Edisto, you’re most likely to get ticketed on Sullivan’s if you’re openly drinking. There’s no public parking lot, so arrive in time to find (free but sparse) street parking.
Where to eat/drink: A visit to Poe’s is a must for anyone on Sullivan's -- order the Tell-Tale Heart or the Gold Bug burger -- while across the street, Home Team BBQ is known for its pulled pork, hearty sides, and frozen painkillers. On an island with several excellent food options, though, the star is a few blocks beyond the main drag; The Obstinate Daughter is a destination unto itself, where you'll indulge in ricotta gnocchi and the Duck Amuck pizza, topped with gorgonzola, roasted grapes, and duck confit. Downstairs, Beardcat’s offers excellent coffee and gelato.