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Downtown Dinner Crawl: Your Progressive Dinner Guide to Charleston

The Cocktail Club

So many mouth-watering, award-winning, crave-worthy (OK, you get the point) restaurants in Charleston, yet so little time. Perhaps one of the best ways to dine out when visiting Charleston is to sample them all! How you ask? Let us guide you through a progressive dinner tour of Charleston, from craft cocktails to appetizers to entrées to desserts (#treatyourself). And the best part? You don’t even have to leave King Street! Scroll through and sip and savor your way through Charleston’s creative cuisine, all along one of our destination’s most iconic streets.

For more foodie fun, discover The OGs: 13 of Charleston’s Oldest Restaurants

Enjoy a pre-dinner drink at this lounge dedicated to the art of the craft cocktail. The Cocktail Club offers an extensive selection of house-made infusions and rare spirits. The rooftop terrace includes a garden that provides fresh garnishes for many of the cocktails.

Sip on an El Matador cocktail (silver tequila + elderflower + southern twist ginger & jalapeno + fresh grapefruit juice) on the rooftop at STARS while enjoying the hustle and bustle of King Street below.

Pull up a seat at Félix to enjoy creative cocktails and small plates served with French flair. Whether you sip on The Polite Parisian or Kir Royal, you're in for a treat.

Experience this Modern American restaurant with delectable cuisine, live music, dancing and award-winning cocktails, all in one energetic atmosphere. The beverage list boasts the largest selection of Irish whiskeys in the Southeast.

As colorful as its namesake flower, Camellias is Charleston’s premier Champagne Bar, featuring an extensive collection of bottle and by-the-glass offerings paired with a decadent selection of caviar, ceviche and tartare. Camellias offers a champagne-inspired cocktail program and a collection of delectable desserts, including the signature Camellias Cake, and afternoon tea.

Cheers with a premier selection of champagne, bourbon and hand-crafted cocktails at this luxury restaurant and bar. Bourbon N' Bubbles boasts a cosmopolitan interior complete with marble countertops, velvet banquettes and bronze fixtures. And our favorite part? Bourbon N’ Bubbles features Charleston's first members-only liquor lockers - for private guests and corporate accounts - to keep their favorites on hand at all times.

The Macintosh offers a soulful menu inspired by Lowcountry farmers and purveyors. Pop in to this this farm-to-table eatery during its Bacon Happy Hour, which features savory small plates and drink specials.

Enjoy a mouth-watering taste of rustic Italian cuisine at Indaco. With their large selection of antipasti, from Focaccia to Burrata to Prosciutto di Parma, it's impossible to choose just one dish to devour. Buon appetito!

Along with its delicious Neapolitan wood-fired pizzas and pastas, Monza's salads do not disappoint. Try the Crispy Chicken Milanese or Caesar with farm egg before diving in to a mouth-watering slice.

The Darling Oyster Bar is a stylish spot favored by both local and visiting sea-foodies. Pull up a chair at the 14-seat raw bar to score a view of bustling King Street while slurping your way through The Darling's savory seafood selections.

Loved most for its tasty thin-crust pizzas masterminded by a Brooklyn legend, Uptown Social boasts 40+ TVs, two double-decker pizza ovens and a wooden rooftop bar complete with a frozen drink machine.

This sophisticated Southern dining spot blends the comforts of a traditional Southern kitchen with familiar regional dishes prepared with the utmost care for quality and flavor. The menu incorporates local fresh ingredients and old family recipes to bring you Southern cooking, Lowcountry style.

The Swamp Fox Restaurant & Bar was named for Revolutionary War hero General Francis Marion and has been serving up classic Southern cuisine since 1924. Try the award-winning shrimp and grits while enjoying live piano music on Thursdays, Fridays and Saturdays.

Receiving the AAA Four Diamond Award, Hall’s Chophouse serves the best cuts in Charleston – from Grass Fed Filet Mignon to Dry-Aged Tomahawk Rib Eye. Slip into the bar for a Lucid Peach cocktail or stop in for Gospel Sunday Brunch to enjoy live music and a steak omelet.

The Ordinary is the second restaurant from James Beard Foundation Best Chef Award-winner Mike Lata, who opened FIG (Food is Good) in 2001. Billed as a classic oyster and seafood hall, The Ordinary is housed in former bank that was built in the 1920s with 22-foot ceilings and 16-foot windows. The bank’s vault door is on display behind the raw bar.

The experience of fine dining in the Forbes Four Star Charleston Grill shines bright amidst the Southern elegance and refinement of Charleston. Reward yourself with an evening of highly creative and uniquely presented cuisine by Executive Chef Michelle Weaver. We invite you to relax in the warm, intimate ambience of this premier Charleston restaurant, and enjoy the soft sounds of nightly live jazz.

Don’t miss Charleston’s first and only cupcake bakery on King Street. Baked fresh daily, there are 12+ rotating flavors to choose from daily, including Bourbon Pecan Pie, White Chocolate Raspberry and Southern Red Velvet. Indulge in the home-baked goodness.

Charlestonian Callie Morey’s hallmark hors d’oeuvre - a delectable, bite-sized biscuit made with finely chopped artisanal country ham, Dijon mustard, and butter - became a made-in-Charleston sensation. Callie's Biscuits have appeared in Saveur, Food & Wine, Southern Living and The New York Times to name just a few. Making it easy to indulge in a late night treat, Callie's Hot Little Biscuit re-opens from 10 PM - 2 AM Friday and Saturday nights!

Feed your inner Cookie Monster at this old-fashioned cookie shop offering a large variety of creative flavors and combinations, from Peachy Keen to Fudge Pecan to a seasonal Strawberry Pink Lemonade and more.

Two scoops, please! It's almost impossible to choose a favorite at Jeni's with their wide variety of flavors, including Brambleberrry Crisp, Middle West Whiskey & Pecan and Frosé Sorbet. Known for their high-quality ingredients and inventive flavors, this ice cream spot is a favorite for a refreshing, sweet treat.