April - June
For us (and, unfortunately, everyone else), spring and early summer is Charleston's finest season. Just when you think the city's cobblestone alley and white columned mansions can't get any more romantic, suddenly the streets are abloom with azaleas, wisteria, honeysuckle and magnolias. It looks gorgeous and smells ever nicer. The weather's warm enough for breakfast on the veranda or drinks at a rooftop bar, but not so sweltering you can't walk down the street without a towel and a bottle of Gatorade. To beat the crowds, try to come on a weekday in early spring. Traffic stays high through most of the summer, though the weather takes a turn for the sweltering in early July. June brings the Spoleto Festival, a massive arts and music celebration that brings Charleston's biggest crowds of the year. Be warned: Hotels book up months in advance and restaurants are running at full-tilt. It's fun, though not necessarily the most relaxing way to get to know the city.
December - February
Winter is Charleston's low season, with more gray days and rain than any other time of year. Yankees will probably be unperturbed, as average highs in the dead of December and January still hover around 60 degrees and lows rarely reach freezing. If you enjoy having the city to yourself, this is a great time to come. (Just bring a jacket and an umbrella.) The weeks leading up to Christmas and New Year are an exception, as visitors come to enjoy streets decked with festive lights and hotel lobbies done up to the max with fully trimmed Christmas trees, opulent ornaments and tinsel everywhere.
October - November
Fall is shoulder season in Charleston. The weather ranges from swampy-hot in September to nippy, but rarely freezing in November. The streets are not as crowded as high summer, but not as damp and chilly as winter. There's a definite downtick in bachelor revelers in the bars of the historic district. Fall also brings the Preservation Society of Charleston's annual Homes and Gardens Tour, an opportunity for the curious public to get inside some of the gorgeous, gated Antebellum mansions of the Historic District. School's back in session at College of Charleston, so the streets of Upper King are once again crowded with trendily dressed youngsters. Depending on your age, this could be a good thing or a bad thing.