An Unusual Way to Spend A Day in Charleston
Charleston is a great walking city and an interesting place to wander, because you always find something you haven’t seen before. Or at least I do. Skip Rainbow Row this trip and find your way through cobblestone lanes and dimly lit cocktail rooms. It feels a little mysterious, kind of cozy, and is a reminder of Charleston’s history.
Grab a cup of coffee and head to Stoll’s Alley. It’s between East Bay and Church Street and is easy to miss from the East Bay side because the entrance is so narrow. It was initially called ‘Pilot’s Alley’, referring to the harbor pilots close to the waterfront. It was later named after Justinus Stoll, who built a house there in the 1700s. The side on Church Street is wide cobblestone, but as you get closer to East Bay, it narrows to about 5 feet and is paved in brick rather than cobblestone. Tall walls and houses make it feel even more narrow. Phillip Simmons, a renowned Charleston ironworker, created some of the iron gates along Stolls Alley. It feels like a moment in history, with its historic homes, greenery, and narrow streets.
Walk toward Longitude Lane, which is between East Bay and Church Street. It’s a narrow cobblestone street with pretty iron gates, ivy-covered walls, and a classic Charleston feel. The building with the arched tunnel was one of the inspirations for the opera “Porgy and Bess”. It’s also one of the prettiest streets to take photos.
Stop and take a look at the Tavern at Rainbow Row, serving liquor since 1686!
Yes, 1686.
It is the country’s longest-operating liquor store. Yes, it even distributed liquor during Prohibition under the guise of a barber shop. They specialize in rare and local spirits and offer weekly tastings. It still contains its original walls and floors. Even more interesting, beneath the store is a system of tunnels used by the Underground Railroad and then again during Prohibition.
Head towards Bar Vaute. It is located below the Brasserie La Banque on the corner of Broad Street and East Bay. Bar Vaute is one of the only below-street bars in Charleston, which makes it feel cozy and secret. It has an Art Deco feel meets French cafe feel and a beautiful bar. You enter through the restaurant and go down a staircase, then through a curtain into a cozy brick-walled little space with soft lighting, cafe tables, and great cocktails.
If you get there during ‘Apero Hour’ between 4-6, be sure to order the French Happy Meal, which includes a burger, pomme frites, and a martini. I also liked the smoked fish rillette, which is served with sourdough. Order a French 75 or an Old Fashioned and enjoy the dark, cozy feel.
After your happy hour, walk down Philadelphia Alley, which runs between Queen Street and Cumberland in the heart of the French Quarter. Philadelphia Alley has had several different names, including ‘Dueler’s Alley’ because it was the best place for a secluded duel with an opponent. It’s brick-paved with moss and vines on the walls, and very ‘Instagram worthy.’ It is a quiet spot within a bustling tourist area and feels like a secret passage.
Head to Scotty Doesn’t Know Speakasy to end your night. The speakeasy was in Big John’s Tavern, which was opened in 1955, and where many of the Citadel cadets hung out. They have remodeled, and what used to look like an ice cream parlor now appears to be a vacant building with a doorbell. When you enter, it feels like your great-grandmother’s living room with lots of Victorian touches and lace. The hostess/bartender will seat you at one of the conversational settings separated by thin curtains. The light is low, the drinks are good, and it feels like you are hiding from someone, which is kind of fun, for some reason.
Maybe because the reminder of Prohibition feels like a part of history and a perfect way to spend a day in Charleston.
