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A Perfect Weekend in Charleston, South Carolina

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Charleston packs a full weekend naturally -- brunch downtown, beach bars on Isle of Palms, barbecue that justifies the trip on its own, and sunset drinks on Shem Creek. Kasey Jane walks through a two-day itinerary that covers all four, plus a few stops most travel guides skip.

Day One: Downtown Brunch to Beach Bars

The weekend starts at Poogan's Porch, a staple brunch spot in downtown Charleston housed in a classic Southern porch-front building. From there, head east to Isle of Palms and The Windjammer, a beachfront bar that runs seasonally. The Windjammer is the kind of place where you end up staying longer than planned -- in this case long enough to run into the cast of Outer Banks.

Poogan's Porch entrance with its yellow clapboard exterior and chalkboard welcome sign

Day Two: Boots, Barbecue, and Shem Creek

The second day opens at Tokova's downtown, a cowgirl boot shop where you can get a pair branded with custom initials on the spot. Then it is over to Sullivan's Island for A Bovo, a permanent jewelry shop -- walk in, pick a chain, and they weld it on your wrist so there is no clasp to lose.

Walking up to A Bovo on Sullivan's Island, a small white storefront at 2216

Lunch is at Lewis Barbecue, which Kasey calls the best barbecue in Charleston without hesitation. The order to know: sliced brisket, fat not lean. The sides hold up on their own.

After lunch, head to Shem Creek for drinks on the water. The specific recommendation is Reds, with a walk up to the Crow's Nest for the elevated view. Dolphins are a regular sighting from the deck.

Night Out: Cocktails, Pizza, and a Ferry Ride

The evening starts at Cocktail Club downtown for gin martinis and live music. Close the night at Benny's Pizza for a late-night slice. If you are staying on Daniel Island, the Daniel Island Ferry runs back downtown and drops you at the French Quarter -- a better way to end the night than a rideshare.

Late night out at a downtown Charleston venue with stage lights and live music

The final morning stop is High Cotton for she-crab soup, a Charleston classic that is easy to overlook if you are focused on dinner reservations.

Key Takeaways

  • Poogan's Porch is the brunch pick downtown; Lewis Barbecue is the lunch pick, specifically the sliced brisket with fat
  • The Windjammer on Isle of Palms is seasonal -- plan your trip around it if beach bars matter to you
  • Shem Creek is the best spot for casual waterfront drinks; Reds and the Crow's Nest are the specific calls
  • Sullivan's Island has two worthwhile stops: Tokova's for custom cowgirl boots and A Bovo for permanent jewelry
  • The Daniel Island Ferry is a practical and scenic way to get between Daniel Island and the French Quarter
  • High Cotton's she-crab soup is worth a dedicated stop before heading home

Published May 26, 2026. Writeup generated from a favorited TikTok.