1. I highly suggest that you get to Charleston at some point before you turn 30 if you haven’t been already. The place is great and seemingly underrated as a vacation destination. It’s a hidden gem to most of the country with only the southeast truly knowing how great it is. The weather is generally good. The male to female ratio is outstanding and the quality of the women themselves is as good as any area in the country. College of Charleston and Charleston Southern are in town and it’s the ideal place for college girls to work in the summer or right out of school. The bars, beaches, golf, and food are all top notch, plus it’s a good-looking town with Southern charm and a beautiful historic feel. You could almost say it’s like a cleaner New Orleans with beaches.
2. There’s never really a bad time of year to head to Charleston. You do have to occasionally be careful of hurricane season, which kind of sucks. (I was once supposed to head there for a bachelor party in August and the shit got railroaded by Hurricane Irene, forcing us to push it back to October and less optimal beach conditions.) Even though there are colleges in town to insure that the fall, winter, and spring seasons are entertaining, there’s enough of a summer scene because of the great weather. The great weather also makes the beach and golf situations that much better.
3. There’s a great debate between staying downtown or by the beach. You’ll enjoy both, but my preference would be to be downtown. You can always drive to the beach during the day and life becomes much easier at night with either walking or a short cab ride to the bars. You’re definitely more in the mix downtown and it’s easier to convince a girl to go home with you when she doesn’t have to sit in a 20-minute cab ride to the beach. Whether you rent a house or get a hotel downtown is up to you, but you’ll enjoy both options. For hotels you can decide between historic (Francis Marion, Mills House, or Charleston Place) or more economic options (Holiday Inn, Spring Hill Suites, or Courtyard by Marriott).
4. If you end up at the beach, you’ll likely end up renting a house. You’ll likely choose between Folly Beach and Sullivan’s Island, a decision that became a lot easier recently when Folly Beach banned alcohol. Everyone used to go to Folly, but now the traffic is at Sullivan’s. Isle of Palm has become more of a family destination, but there are some nice houses for larger groups. There is also good Holiday Inn at Folly Beach if that ends up being where you rest your head.
5. If you can somehow get a round of golf on the Ocean Course at Kiawah Island, then God bless you. It’s arguably the nicest course in the country and home to a recent PGA Championship. If you can’t, you’ll still be able to find another great looking course to swing the sticks. Patriots Point in Mount Pleasant is a great public course on the harbor with nice views of downtown. Dunes West nearby is also a nice option with nice scenery of the area. The Links at Stono Ferry is just south of downtown and provides a challenging course recently voted the South Carolina course of the year.
6. There are also a lot of good restaurants in Charleston because there was a large migration to the area from New Orleans’ best chefs after Hurricane Katrina. The best chef in town is Sean Brock who runs the most popular restaurant in town, Husk, along with McCrady’s. Anything you order at Husk will be good, but it’s known for its fried chicken skins, cheddar pimento crostinis, corn bread, and anything pork. Shellfish dominates the menu at The Ordinary, but there’s a reason it was nominated as one of the best new restaurants in 2013. If you’re in need of a steak while in town, Oak Steakhouse recently made a list of best U.S. steakhouses and Halls Chophouse is another local favorite. (Personally I’d focus your meals on the more local food as you can get a good steak anywhere.) Cypress, known as one of the best restaurants in town, has the best charcuterie plate in town and a sexy bar to match. Hymans and Bowens Island are probably the two best places to go for seafood, which you should have given that you’re staying near on the water.
7. There are plenty of options for brunch. You can get bottomless mimosas for $10 a person at Toast, where you’ll obviously enjoy the well-known French toast. You can end up at Magnolias, where almost everything has seafood. The crab, shrimp, and grits is so good that it’ll make you fall out of your chair. Hominy Grill, one of the favored classics in town, is another option for brunch. The house made banana or ginger pumpkin bread will leave you with something you’ll remember for a long time. Pearlz Oyster Bar lives up to its name with the best oysters in town. Poe’s on Sullivan’s Island provides a cheaper yet still good alternative with a good burger among other things. Fiery Ron’s Home Team BBQ, which has two locations in the area, was recently voted the best ribs in the country. And worst case there’s always the Chic-Fil-A located in the C of C’s student union.
8. There are plenty of fun bars on Bay Street and Market Street near the water. That’s generally where you get an older, less college-y atmosphere. Anyone you talk to will tell you to stop into Blind Tiger for a good looking crowd with a nice, outdoor area. The combo of Henry’s House & NV Lounge gives you a bar on one side and a club on the area to provide the best of both worlds. The rooftop at Vendue Inn is a classier spot with really good views of the city. Mac’s Place is a laid back atmosphere to grab some beers and maybe play a little trivia or golden tee. Tsunami is big on Tuesday nights with the young crowd and rolls out a lot of house music.
9. You can hit up the King Street area, which has a diverse scene between the party-focused kind and the more sophisticated folk. Midtown Bar & Grill is a good college-like scene to pick up chicks. Silver Dollar up the street is another place to pull hands when the clock gets close to closing time. Trio is arguably the most fun bar in the area on Fridays and Saturdays and is easily one of your best late night options. King Street Grille gives you the best TV situation in town for sports watching. Proof, Closed for Business, The Belmont and The Rarebit are four places to head for fancy cocktails if you’re looking to class up your night. There are also some decent bars on the beach. Red’s (Mount Pleasant), The Windjammer (Isle of Palm), and Rita’s (Folly Beach)
10. Your night doesn’t have to stop when last call comes and goes. The Southern Belle strip club has a tremendous reputation and is the place to go after hours in Charleston because you can BYOB. Regular girls (aka not working girls) even go there to hang out. You can buy your own beer at the gas station across the street and bring it right in. It’s also been the location of a legendary story involving a threesome between a local girl, a stripper, and a regular fun-loving bro, so it gets my thumbs up.