The Must-Use Itinerary for a Weekend Getaway to Charleston

The Must-Use Itinerary for a Weekend Getaway to Charleston

So you’ve decided to visit Charleston for the weekend. Well congratulations, it’s the most beautiful and historically rich city on the United States’ east coast!

And because there is so much to see and do in Charleston, it’s hard to come up with a solid itinerary that incorporates the best of Charleston into one weekend. Well not to worry, we’ve come up with the ultimate weekend getaway itinerary for you!

See below for our ultimate weekend in Charleston itinerary:

Prep before your trip: Go to for all the upcoming events in the Charleston area or visit the Charleston Harbor Tours Twitter page for up-to-date information on Charleston happenings (follow us @ChasHarborTours). You may be visiting during a festival or event that you’ll want to take part in!

Also, make sure to take a look at the weather forecast before you visit. Charleston is typically sunny year-round, but we do get some occasion rain and cold fronts. It’s best to be prepared so as not to ruin your trip!

Day 1, Friday: Arrive on Friday to the Holy City

Upon arrival to Charleston in the afternoon, you will check in at your downtown hotel or Charleston bed-and-breakfast. See below for our favorite hotels and bed-and-breakfasts in downtown Charleston:

  • 2 Meeting Street Inn (B&B)
  • Charleston Place Hotel
  • Market Pavilion
  • Marriot (courtyard on the water)
  • Calhoun Street Marriot
  • Francis Marion
  • John Rutledge House Inn (B&B)
  • Battery Carriage House Inn (B&B)

After checking into your Charleston hotel or bed-and-breakfast, it’s time for cocktail hour!

Here are some of our favorite places to grab a cocktail or glass of wine:

  • Amen Street Fish & Raw Bar (great for martinis and cosmopolitans! More of an elegant flare)
  • Social (great for a glass of wine with a casual yet sophisticated atmosphere – great happy hour menu, as well)
  • Burn’s Alley Neighborhood Bar (here’s where you would go for a super laidback, dive bar feel – great for grabbing a brew!)
  • Fish (fantastic signature cocktails with a sophisticated atmosphere)
  • Juanite Greenburg’s (when you’re in the mood for a margarita, here’s where you want to be – casual, laidback atmosphere)
  • The Recovery Room (dive bar with great prices!)
  • Henry’s House (great rooftop bar)
  • The list goes on and on . . .

After enjoying some drinks in the Charleston bar, lounge, and club scene, it’s off to a Theatre 99 to watch a comedy show! Theatre 99 offers a variety of comedy shows, including improv shows and standup routines. Be sure to check them out online at

Day 2, Saturday: Explore Charleston’s Culture

Awaken to a beautiful morning in downtown Charleston before heading to the Charleston Farmer’s Market at Francis Marion Square. Grab a bite to eat at one of the food stands, which include a creperie, coffee and waffle stands, and pastry booths. Then, travel throughout the market to find unique handmade crafts, works of art, traditional Charleston cuisine, and more!

If you woke up a bit late for the Famer’s Market, no worries, head to The Bagel Shop

at 41A George Street before taking a stroll down King Street for some boutique shopping. End at the Charleston City Market on Market Street where you’ll find traditionally made Charleston crafts, souvenirs, and art.

king street

Next, it’s off to Rainbow Row and the Charleston Battery to witness the beautiful Charleston harbor and traditional Charleston architecture. If you’re down for some more cultural exploration, take a tour of Museum Mile. Click here for information on Museum Mile.

Spend the rest of your afternoon relaxing and prepping for dinner!

Tonight, enjoy traditional Lowcountry cuisine at Charleston’s finest. Below are some of our favorite restaurants in Charleston that offer authentic Lowcountry fare:

  • Magnolia’s
  • Slightly North of Broad (S.N.O.B.)
  • Hominy Grill
  • Cru Café
  • 82 Queen
  • Poogan’s Porch
  • Charleston Grill

After a tasty dinner, it’s time to spook yourselves out on an authentic Charleston ghost tour with Bulldog Tours! Click here to learn more about their ghost tours.

Charleston City Market

Day 3, Sunday: Immerse Yourself into the History of Charleston

Today is an exciting day filled with fascinating Charleston history and beautiful landscapes and views.

After enjoying breakfast, head over to Patriot’s Point in Mount Pleasant to hop aboard the USS Yorktown (an aircraft carrier that served in WWII) to explore WWII history, observe fighter planes, and tour the insides of the aircraft carrier.

Another option for exploring the history of Charleston is to embark on a combination tour that includes a 90-minute historic harbor tour (narrated aboard The Carolina Belle), plus a Carriage Tour of downtown Charleston, plus admission to Boone Hall Plantation (one of Charleston’s most historic and stunning plantations). Click here to learn more about this combination tour.

boone hall

charleston carriage tour

charleston harbor tour

After you’ve explored the historical side of Charleston, it’s time to head back home and start planning your next weekend getaway to Charleston!

Bon voyage!

This is a great post to share with your wedding guests if you are planning a destination wedding in Charleston! Spread the love!

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