You’ve Gotta Do This! A Charleston Cocktail Crawl

July 6, 2015 | By | Comments (10)

Photo courtesy of Icebox Bar Services

Charleston, South Carolina knows hospitality. And it definitely knows how to have fun. So, it’s no surprise that this divine place, appropriately known as the Holy City, has no lack of watering holes. The best way to see Charleston? Cocktail crawl through it. Tell your tour guides, (bartenders), you’re on a mission to taste the spirit of the city and you’ll end your evening drunk on its allure.

Start your afternoon with a hearty appetizer and house made beer at Edmund’s Oast at the top of the Peninsula. Not in the mood for beer? Ask Teddy or any of the talented bartenders to mix up something local. In addition to several local breweries, there’s three craft liquor distilleries in Charleston too! You’ll feel like you’re in a high scale German brew house as they treat you to custom beers and cocktails like you’re an old friend.

Next up, feast on chargrilled oysters and a glass of rosé, on tap might I add, at Leon’s Oyster Shop. This place focuses on kegged anything and indescribably good oysters and fried chicken. At this point, you may want to order a big plate of chicken for the table… you’ll be glad you did.

After you’ve had your rosé fix, walk south on King Street and pop in to Prohibition. This flapper-era bar has innovative infusions and drink features that will quench your thirst amidst the downtown heat. The hot spot for discerning 20-somethings, it’s the bridge between the newer part of Charleston and what’s to lay ahead down the Peninsula.

Now… time to catch the sunset. It’s just a quick walk, and even quicker bike taxi, to The Rooftop Bar at The Vendue Inn off of East Bay Street. You will really feel like a local as you pass Marion Square with a notorious Charleston happy hour grin and realize just why this city is so dang friendly. As the elevator door opens onto the rooftop and the warm breeze kisses your face it’s nearly euphoric. With a cocktail in hand, you’ll get a 360-degree view of the peninsula.

Downstairs, the cobblestone streets that are your pathway were once the same for frequent Charleston visitors like George Washington and Andrew Jackson. Some of the oldest in the nation, they’ll lead you to classic Charleston spots like The Gin Joint. Let your senses do the talking; pick a few adjectives from the menu and the bartenders will make a cocktail just for you.

Now that you’re on East Bay Street, you can’t leave without having an Oyster Shooter at Pearlz Oyster Bar. A raw oyster in a shot glass topped with vodka and cocktail sauce, this is a regular lowcountry libation that can be found from backyard BBQs to black tie affairs.

Round off your Lower Peninsula adventure with a toddy on the courtyard at historic Blind Tiger Pub on Broad Street. The massive shady trees and brick walls that date back to the 1800s will immerse you in old Charleston.

Now it’s time to head back up King Street, I’d suggest a bike taxi now, and finish off your Charleston Cocktail Crawl at The Cocktail Club. Dimly lit, it’s the ideal place to end your evening. You’ll realize here that it really is the little things, like bleu cheese stuffed olives to order, which make martinis and life, so grand.


  1. Lindsay Lee

    This is the best step-by-step article! How fun!!!! Let’s all just pack our bags and head there now!!! CHEERS!!!!!!!!

    July 11, 2015 at 11:52 am
  2. Thursday Things: Spring 2016 Trends • The Kentucky Gent

    […] of travels, I really want to go back to Charleston, especially after this Charleston Cocktail Crawl that I ran across the other […]

    July 9, 2015 at 10:05 am
  3. Lauren

    Love, love, love!!!! Amazing article

    July 8, 2015 at 11:30 am
  4. maryhelen tomlinson

    AMAZING! want to go to everyone of those places right now!

    July 7, 2015 at 3:15 pm
  5. Lauren

    Wonderful article! Very well written.

    July 7, 2015 at 11:50 am
  6. Amanda M

    Great article!!!!

    July 6, 2015 at 9:38 pm
  7. Brenda

    Excellent article! I’m ready to make plans to get back to one of the most fabulous US cities I’ve ever visited! Cocktail Crawl sounds like great fun!

    July 6, 2015 at 7:58 pm
  8. Louise

    Fabulous article! Can’t wait to follow your suggestions!

    July 6, 2015 at 7:43 pm
  9. Sean is LocalByChoice

    Well written piece.

    Take it from a local former concierge at an upscale hotel, this girl nailed it!

    July 6, 2015 at 6:00 pm
  10. Doug

    Makes me thirsty for my favorite city in the whole wide world. I’m on my way back next month. 😉

    July 6, 2015 at 5:11 pm

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