Charleston’s nickname may be the Holy City, but these days, there’s more action on King Street on Saturday night than on Sunday morning. The city still balances the pious with the party— Sunday brunch features a colorful mix of seersucker-clad sophisticates and bleary-eyed frat boys nursing a breakfast stout. Fortunately, it’s a place where sunny and warm is the regular forecast, so if you fall into the latter category, you can keep your shades on.
Best of all, there’s always a beach nearby, so even if your pasty skin gets toasted on a sweltering August afternoon, you can still drown that hangover in all-healing salt water. If for any reason none of that seems appealing, then take a gander here. However, if you and the guys have three days to explore/consume/defile Charleston, then we’ve got your itinerary.
10 a.m. Check in at The Hyatt
Land at Charleston International Airport and hop in an Uber ($25ish) to the Hyatt Place Charleston/Historic District. In this city known for accommodations, you can easily find $500-a-night hotel rooms with marble floors and linen sheets. But assuming that you’d rather splurge on booze, this new addition to downtown’s hotel scene will suit you well for around $200/night. Rooms are modern and comfortable, and it’s smack in the middle of the Upper King Street bar district. Best of all, the Hyatt’s rooftop bar, Pour Taproom, has 70 draft beers with self-fill, pay-by-the-ounce taps, and its view of the steeple-speckled skyline is among the city’s best.
1 p.m. Lowcountry Lunch at Hominy Grill
Hominy Grill, James Beard award-winning chef Robert Stehling’s cathedral to grits and Southern grub, makes a fine introduction to Lowcountry cuisine. Order a Charleston Nasty Biscuit for the groom—it features a massive dollop of sausage gravy and cheddar over an impeccably fried chicken breast. Also of note are the Shrimp Bog (an amalgam of Carolina gold rice, local shrimp and andouille sausage) and the Chicken Country Captain, a dish that blends Charleston’s terrain to its seafaring past. Wash it down with a Dark & Stormy, whetting your lips for the liquor to come.
4 p.m. Boat to Fort Sumter
During the Revolutionary and Civil Wars, whoever held Fort Sumter controlled which boats came in and out of Charleston. Strategically located at the mouth of the harbor, the first shots of the Civil War were fired at the fort by Citadel cadets after South Carolina seceded. Even if that doesn’t excite you, Fort Sumter is an island with terrific views of two lighthouses and the downtown peninsula, and you get to take a boat ride to get there. From March 15 through August 20, the 4 p.m. ferry will let you skip the heat of the day and the crowds. Outside of those dates, adjust your schedule for the 2:30 pm departure. The ferry terminal is at Liberty Square, next to the Aquarium, and is a five-minute drive from Hominy Grill.
8 p.m. Fried Seafood Dinner at The Wreck
When friends come to town and want old-school seafood, locals take them to The Wreck. This Shem Creek institution has character, from the boiled peanuts appetizer to the cube of fried grits that accompanies every basket of shrimp, scallops and oysters. All you have to do is circle what you want on the paper menu—go big and opt for the platter, then go bigger and gorge yourself on the key lime bread pudding. After dinner might also be the ideal time to drop a call to that significant other. After all you’re going to be getting very boozy very quickly.
10 p.m. Bar Crawl on Upper King Street
Upper King is where the newest and hottest bars in Charleston tend to open, venturing ever further north. There are over a dozen spots for bespoke cocktails or lively dance floors within a few blocks’ radius of the Hyatt, meaning those in your crowd who hang tough after 1 a.m. won’t have far to stumble home. Here’s your crawl plan:
A.C.’s Bar and Grill (467 King St.) doesn’t have a website, but they do have a shit ton of ice cold Miller High Life (champagne!) and a couple of pool tables. This is King Street’s original dive, so treat with respect. Republic Garden & Lounge can feel a little too “velvet rope” for Charleston, but you’re here for a bachelor party, so dancing with girls in ridiculous heels to techno beats is part of the game. Just enjoy it. There is a patio to escape to if you need fresh air or prefer live music (there’s typically a band on the outdoor stage).
Stars Rooftop Bar, on the other hand, can feel like stepping into the dining room at Gatsby’s mansion, but you’re headed straight for the roof. This is where your buddy will make an ass of himself hitting on College of Charleston coeds, who flock here in droves. Prohibition transforms from a Dixieland jazz saloon into a full-on dance party around 10 p.m. Each vibe has its appeal, and it’s fun to watch the rapid metamorphosis when the New Orleans-esque band cedes the floor to the DJ. The Recovery Room Tavern sells more cans of PBR than any other bar in the country. For real. Play some foosball, eat some tater tot nachos, and go to bed.
11 a.m. Brunch at Callie’s Hot Little Biscuit
This is not a time for slow service and a hungover waitress (you’ve got your own hangover to worry about). This is a damn-near emergency. Callie and her Hot Little Biscuit have your fix, in easy walking distance, to boot. You’ll be in and out the door in 10 minutes with a sausage, egg, and pimento cheese biscuit that will save your soul. Go ahead and add the country ham…maybe the bacon gravy too.
1 p.m. Flyboard with Hydrofly Water Sports
The “office” for locally owned outfit Hydrofly is a two-story Tiki-hut-house-boat moored in the Ashley River—a good sign of the laidback experience to come. Although flying 20 feet in the air, propelled by a water-fueled rocket pack strapped to your feet, is hardly “chill.” It’s a surreal, badass experience, akin to skydiving in awesomeness. Hydrofly has packages designed for bachelor parties, including wakeboarding and tubing sessions. Wrap up the afternoon floating in the river and drinking beer around the Tiki raft.
5 p.m. Oysters at The Ordinary
In a city built on seafood, the new standard bearer, The Ordinary, is right outside your hotel. Chef Mike Lata’s seafood hall is the time to go big, and that means ordering at least one of the $125 triple-decker seafood towers, a shining palace of flounder crudo, smoked oysters, local littleneck clams, raw snapper, and whatever else is just off the boat.
7 p.m. Second Dinner (and Mezcal) at Minero
You didn’t choose Charleston so you could go hungry. Sean Brock is the current king of Charleston chefs, and his ode to Mexican food, Minero, is a cantata of beauty. Order one of everything from the appetizer menu, including the chicken wings (doused with Valentina hot sauce in a paper bag) and the chilaquiles, a melted pan of chips, beans, queso, and avocado. If a seafood-averse buddy went hungry at the Ordinary, order them the burrito, a beast of legend that’s fortified with Hoppin’ John. Wash it all down with their unrivaled selection of single village and wild agave mezcals.
9 p.m. Get Wild on the Market
Fortified with fermented agave juice, set out into the city. At Minero, you’re in the French Quarter—one of the oldest neighborhoods in Charleston, where some cobblestone streets still exist. On Friday and Saturday nights from April to December, Market Street hosts the Night Market until 10:30 pm, so any betrothed or married buddies should sneak away from dinner to pick up their obligatory handmade local jewelry or a box of pralines to take home to their sweetie. Then join back up to party at these stalwart Charleston hangouts:
The Rooftop at the Vendue was Charleston’s rooftop bar before rooftop bars were a thing, and it’s still consistently voted the best by locals. The only downside is the midnight closing, so start here first, make some friends, and invite them along to close the night at one of these:
The Griffon is just across the street from the Vendue, meaning it’s slam-packed from midnight to 2 am. That’s okay though—the tight environs fire up the band, until the room is one moving mess of happy humanity. This bar prides itself on good beer—almost every local brewery is represented.
The Blind Tiger Pub has long been the hangout of the lawyers, bankers and government workers employed around Broad Street’s “Four Corners of the Law.” It’s historic digs and attractive courtyard also make it one of the most happening gathering places on weekend nights.
11 p.m. Stripclubbing at King Street Cabaret
Charleston’s strip clubs are all in North Charleston and the Northern Neck area of the peninsula, and they close at 2 am, meaning that you’ll give up valuable time to party downtown if you go. King Street Cabaret is the best of the spots close to downtown, but in a town full of beautiful women, you may not find it necessary.
11 a.m. Rehydrate at Renew Medical IV Hydration
If you wake up feeling like rolling back over and dying, there’s a fix just a couple blocks away at Renew Medical. You know you’re in a drinking town when a spa that specializes in IV hydration can claim prime real estate on the main drag. Walk down to 442 King St. and get hooked up to the “Hangover Boost” IV drip for a new perspective on life and the medical industry.
1 p.m. Eat Meat at Lewis BBQ
There are dozens of excellent brunches in Charleston. What do they all have in common on Sunday? They’re busy. So say thank you to Austin-bred pitmaster John Lewis for opening Lewis BBQ at 11 a.m. on weekends. Try not to drool as you order brisket, pulled pork and “hot guts” by the pound. Get a double helping of the green chile corn pudding. Eat. Have a breakfast margarita. Eat some more.
3 p.m. Beach Time on Folly
It’s time to veg out, and Folly Beach is the ultimate spot for clearing your schedule. Hopefully you’ve packed according. Post up near the Folly Beach Pier if you want access to drinks—alcohol isn’t allowed on the beach, but there’s an open-air bar on the pier where you can drink in the sun and take in the view. If you’re feeling extra ambitious, rent a fishing rod from the on-site tackle shop and try to catch a shark. Just be sure to let it go, and don’t hook a surfer.
7 p.m. Food and Drinks at Loggerhead’s
Folly has two dozen of bars and restaurants, and Loggerhead’s Beach Grill is one of the best for groups. It’s also not overly touristy, and has decent seafood and pub fare to please any appetite. There’s often a local crowd here for big games, but you’re here to sit around the outside bar (including a cooler built into a VW van), listen to the waves on the ocean, and swap war stories from the last three days.
9 p.m. Painkiller Cocktails at Surf Bar
Just around the corner from Loggerhead’s, the party gets going at Surf Bar every Sunday around 9 p.m. There’s a live band every week, making Sundays on the beach feel like a second Saturday night. The funky bar lives up to its name—order a Painkiller cocktail, grab a partner, and work the dance floor until last call.
You slept for like, four hours. Now you’re at the airport and your flight is delayed. You feel like death. Fortunately, there’s a solid restaurant at the Charleston airport, and you walk right past it en route to either terminal. Find Caviar & Bananas. Order a Cuban sandwich and an ice coffee. Melt into your seat on the airplane and realize that it’s finally time for that pre-wedding diet cleanse your bride-to-be has been nagging you about.