Charleston, established in 1680 on the nose of the peninsula between the Cooper and Ashley rivers, is a wedding cake of a city, all frilly colonnades and wrought-iron curlicues. It's one of the most visited cities in the South, and in high season it can be a rather cloying confection, with swarms of bus tourists, aggressive souvenir hawkers, and drunken bachelorette partiers marinating in the South Carolina heat. But you'll avoid all of that by coming in the late fall or winter, when the breeze blows off the harbor and the Historic District reverts to feeling like a lovely, lazy European port town.

Just be sure to come hungry. With its mix of French, English, Caribbean, and West African cultures and its wealth of fresh seafood, Charleston is a city made for gourmands. While some of Charleston's longest-lived and most beloved restaurants have been floating on their reputations for decades, Hyman's Seafood is still the real deal, even after 115 years. And the ridiculous, up-the-block lines that can deter even the most stoic high-season tourist are quieter by fall. Try the decadent sherried she-crab soup. Across from the old City Market (once Charleston's main public food market, now a beehive of souvenir stalls), Anson is your best bet for upscale South Carolina coastal cooking. Think roasted oysters in sherry mignonette, local triggerfish with currants, and Marcona almonds.

Charleston's elegant architecture is best appreciated during a long stroll. The most quaint winding back alleys are found south of Beaufain and Hasell streets. And don't miss Rainbow Row, a photogenic stretch of brightly painted East Bay Street homes. At the southern tip of the island, the Battery is lined with 19th-century merchant's mansions. You can also tour the Edmonston-Alston House, built in 1828 and outfitted with period antiques. Spend the night at the Battery Carriage House Inn, a harborside carriage house that was nearly destroyed during the Civil War in the Siege of Charleston. Elegant rooms are about a third cheaper during the shoulder season. Beware: They're said to be haunted by a nasty pirate ghost.

Nightlife in the Historic District is a bit of a country-clubber scene, so put on your pearls or your loafers (sans socks). And don't miss the sunset happy hour at the Rooftop at Vendue Inn. This sprawling open-air bar has the kind of dreamy harbor views that make you want to propose to a stranger. Head north on King Street for bars with a slightly edgier, more local vibe (and better prices).

To learn more about the city's history, check out the Charleston Preservation Society on King Street, which has a bookstore specializing in local history, architecture, and culture.

The three restored plantations on Ashley River Road, about 20 minutes outside of the city, make for worthy day trips. But if you have time for only one, Middleton Place, with its stunning classical gardens and working rice fields, is probably your best bet, as long as the weather's good.

About an hour south of the city, the resort community of Kiawah Island is the place to treat yourself to a golf weekend. Shoulder-season rates at the ultra-luxe Kiawah Island Golf Resort are less than half of the high-season price, meaning savings of more than $300, which should leave you plenty of cash for scotch, steaks, and the rest of your necessary luxuries. Beware the gators lurking in the sand traps (not kidding).