48 Hours in Charleston: A Food & Fishing Guide to Fried Chicken, Oysters, Caviar, and Cocktails
Charleston doesn’t just feed you—it pulls you into its rhythm. In 48 hours, we found ourselves living by word of mouth, trusting sandwich shop owners, bartenders, and our own curiosity. That’s the real secret here: Charleston is best explored one bite, one sip, and one conversation at a time.
Day One: Trust the Locals
Where We Stayed
We set up shop at Pacific Blue, a Town & Island rental just a five minute walk from King Street. Fully furnished, cozy, and within stumbling distance of Holy City Bagels, Seahorse and Chubby Fish, it turned out to be the perfect home base for a food-driven weekend.
The Sandwich that Started it All
Our first stop was The Pass, a little Italian sandwich shop Harris had spotted on an Instagram reel. We ordered the Tacony-6931 and quickly struck up a conversation with the owner, Anthony. Italians don’t mess around when it comes to food, and when Anthony leaned in and said, “You need to go to Leon’s,” we listened.
Leon’s: Frozen Gin & Tonics, Char-Grilled Oysters, and Fried Chicken
Leon's Fine Poultry & Oyster Shop has the kind of casual neighborhood vibe that makes you feel like you’ve been there a hundred times before. We bellied up to the bar and bartender Stephen immediately confirmed Anthony’s advice: “Frozen gin & tonic. Trust me.”
He wasn’t wrong. Crisp, citrusy, refreshing—it was one of those life-changing drinks you’ll compare all others to. Then came the food: the “world-famous char-grilled oysters”, bubbling with butter and parmesan, alongside the “2-Piece dark meat fried chicken”, crispy on the outside and impossibly juicy within. It was comfort food at its absolute peak.
Stephen asked if we had dinner plans. When we told him we hadn’t thought that far ahead, he leaned in with a grin and said, “I’ve got just the spot—Chubby Fish. Order the caviar sliders, the pork belly, and the curry. But you need to be in line by 4:30 if you want a table.” Said another way, they do not take reservations by phone or online. Solid tip.
The funny thing? Harris had already been talking about Chubby Fish all week. Just days before our trip, it had been named one of the New York Times Top 50 Restaurants in America. With Stephen’s endorsement, the decision was sealed.
Seahorse & The Warm-Up
By 4:45 Harris had our names on the Chubby Fish list and, following the hostess’s advice, ducked into Seahorse next door to wait. I joined him, and we sampled our way through their inventive cocktail list: the Charles Town (bourbon, peach, benne seed, and tea, complete with a seahorse ice cube), the Fort Kochi, La Serenissima, and the Motril. Each one was as surprising as the next—a playful pre-game before dinner.
Chubby Fish: The Main Event
By 6:30, we were inside Chubby Fish, one of Charleston’s hardest-to-get tables—and for good reason. With only 40 seats, an open kitchen, and a chalkboard menu that changes daily, the place buzzes with anticipation.
It’s not just hype. Chubby Fish has been recognized nationally: back-to-back James Beard nominations, including Finalist for Best Chef Southeast in 2024 and Semifinalist for Outstanding Restaurant in 2025, plus nods from The New York Times, Food & Wine, and Bon Appétit.
We took full advantage of our good fortune and ordered a third of the menu board:
Perky Sea Cups Oysters with tosazu jelly
Caviar Sammich’ on a tater roll with crème fraîche
Big Eye Tuna Belly Toast with tomato, aioli dulce, and benne seed
Charred Lamb Rib with romesco
Black Grouper Curry with eggplant, peanuts, chili, and rice (a dish that rivaled anything we’ve had in Thailand)
Bone Marrow with Shrimp Tempura & Spicy Mayo
Summermelons with pork belly, almond, and herbs to close it out
It was indulgent, over the top, and unforgettable. The only downside? No cocktails—beer and wine only. But that just gave us an excuse to “cartwheel” back to Seahorse for a nightcap.
Day Two: From Bagels to the Boat
Morning Fuel at Holy City Bagels
After a solid night’s sleep and a full belly, we strolled down to Holy City Bagels to refuel. What started in 2017 at the Charleston Farmers’ Market has since grown into a food truck and finally a brick-and-mortar shop at the corner of Cannon and Coming.
We split a pastrami reuben on a salt bagel and a lox deluxe on an everything bagel, washed down with cold brew. It was the kind of breakfast that demands you linger a bit before the day gets going.
Casting Off with Tall Tide
By afternoon, we were at Sunset Cay Marina on Folly Beach, climbing aboard with Captain Gates Roll of Tall Tide Fishing Adventures. One of the perks of Charleston? You can leave your rental in downtown, grab an Uber, and be casting a line less than an hour later. Just 20 minutes from King Street, and suddenly you’re in the salt air with dolphins cruising by your boat.
Gates knows these waters like the back of his hand. With more than 20 years of guiding experience, he’s equal parts fisherman, teacher, and storyteller—the kind of captain who knows not just where the fish are, but why they’re there. He put us on a four-hour tour that checked every box: chasing bull reds and tarpon in the surf, a surprise blacknose shark, then into the flats where we found puppy drum and flounder waiting.
We lost track of time chasing fish, but Gates didn’t. Knowing we were running behind for dinner, he pulled a guide’s trick and dropped us at the public ramp on Center Street instead of back at the marina—shaving precious minutes and dollars off the Uber ride into downtown. That’s the difference between fishing with a pro and just renting a boat.
Raw Lab: Dining as Discovery
After a quick shower and a Seahorse cocktail, we made our way downtown to Raw Lab, tucked into the Port of Call courtyard on South Market Street. Here’s the thing: you can’t describe Raw Lab. You have to experience it. And you’d better do it soon—Chef Kevin Joseph is taking his final bow in Charleston on New Year’s Eve 2025.
Over multiple courses, Kevin takes you on an omakase-style journey of marine cuisine including an unparalleled oyster and caviar service, rare salts, and wines from five continents. He calls it the delta between eating and dining: discovery.
The Perky Sea Cup oysters locally sourced from Charleston Oyster Farm set the tone. Shucked in front of you and served as a half-dozen flight, each oyster is the control while the accouterment shift like variables in an experiment:
One with freshly grated horseradish and lemon, a bracing classic.
Another with freshly grated wasabi rhizome and lime, a sharp green heat that wakes up every taste bud.
Three more dressed in distinct mignonettes, each layering acidity and aromatics in their own way.
And finally, a cold-smoked version that lands like a curtain call—rich, sultry, and unforgettable.
From there, the experience unfolded into a crescendo of creativity:
White Sturgeon Caviar – from monkey brain to lizard brain, the caviar trip.
Prosciutto-Wrapped Unagi – smoky, salty, and sweet, a flavor bomb you don’t forget.
Lobster Bisque – silky, rich, and layered, like the sea distilled into a bowl.
Shrimp Ceviche – refreshing and sharp, the perfect palate cleanser.
The Pink Taco – playful and just a little mischievous.
The James Brown Lobster Caesar Salad – funky and soulful enough to live up to its namesake.
Salmon Avocado Tapenade Stack – bright and balanced.
But a list doesn’t do it justice. Just stop reading and book a seat on Resy before it’s too late.
We capped the night with a tequila shot and called it lights out.
One Last Bite
The next morning, before hitting the road, we made one final stop—because no Charleston weekend is complete without a true Lowcountry brunch. Virginia’s on King was the perfect choice.
We left no calorie behind:
Fried Green Tomato Benedict – with Tabasco hollandaise and crispy home fries..
Virginia’s Fried Chicken (dark meat, of course) with mac & cheese and collards.
Shrimp & Grits – creamy, rich, and one-hundred percent Charleston.
Only then, fully and finally stuffed, did our moveable feast reach its conclusion. Waters to-go, doggy bag in hand, and wheels up back to Atlanta.