A Weekend in Charleston: Your Guide to a Historic & Relaxing Weekend

Taking a weekend trip to Charleston? Check out where to stop, where to eat, and where to stay, on a weekend in Charleston!

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Curious about a weekend in Charleston?

Charleston, South Carolina is a gorgeous and historic Southern city - not to mention one of the most-visited spots in the US, year after year! Somehow, Charleston manages to accommodate an ever-increasing number of tourists, without losing its authentic, relaxed charm.

With an emphasis on good food, great shopping, and a laid-back way of life, Charleston has a lot to offer for even a quick visit. Charleston can easily be experienced in just a weekend - let's discuss some highlights of a weekend in Charleston!

A Weekend in Charleston: Getting There

Charleston is served by the recently renovated Charleston International Airport, which is not only nice, but also incredibly close to the downtown, making an Uber easy transportation to your hotel and/or Charleston's historic district.

If you'll be driving to Charleston, the city's small size means parking is widely available and doesn't come with the sticker shock of a stay in Chicago or NYC. For example, valet parking at The Dewberry, the nicest hotel in Charleston, is $40/night.

​A Weekend in Charleston: History

No blog post here at Pints, Pounds, & Pâté would be complete without just a bit of history to get us started, before we move onto fancy hotels and dinners!

Charleston's namesake, England's King Charles II, gave the land that became Charleston to a group of his supporters in return for their loyalty after the English Civil War, and South Carolina quickly grew into a wealthy colony. Later in the 17th century, Charleston became a hotspot for pirates, who took advantage of an alternatively corrupt and powerless city government (the city now plays on that unique history with more than its fair share of pirate-themed activities). 

Broad Street, Charleston

In the Antebellum period, Charleston's trade and farming wealth increased, and many of the city's mansions were constructed, many as second "city" homes for wealthy low country, slaveholding planters. A hotbed of succession during the Civil War, South Carolina fired the first shots against the Federal Government at Fort Sumter in 1861. You'll hear plenty about all of that during your stay!

Charleston has a vibrant African-American community, including the Gullah culture of the people who inhabited the nearby islands. Gullah culture has given us those gorgeous sweetgrass baskets you'll see for sale throughout Charleston, particularly in the City Market. For more on Gullah cultural experiences in Charleston, check out this blog post!

Today, Charleston is a relatively small city, for how well-known it is, with less than 800,000 in the "Charleston region."

A Weekend in Charleston: Where to Stay

The Dewberry, Charleston

To make it a true weekend getaway, stay at Charleston's best hotel, The Dewberry. With a gorgeous combination of historic, Southern ambiance and updated, mid-century modern decor, The Dewberry sparkled at every turn. And the Living Room (lobby) Bar is one of the coolest I've seen, this side of the pond.

Check out The Dewberry's rates on Booking.com.

Oh and did I mention The Dewberry has the most phenomenal rooftop bar in the entire city?

​A Weekend in Charleston: Shopping on King Street

It's hard to pick a favorite activity in Charleston, but shopping on King Street is certainly one of mine! It seems to have every nice shop I'd have asked for, combined with a nice mix of local boutiques.

For all the details and can't-miss shops, check out where to shop on Charleston's King Street!

​A Weekend in Charleston: Sights to See!

Stroll through the historic residences

Some of the most beautiful residential streets in the U.S., Charleston's Meeting, Church, & King Streets, as you walk toward the water, make for a perfect Saturday morning strolling location!​ The majority of these homes are privately owned, so Zillow in this area makes for an exciting adventure before or after your trip!

Notable homes include the Miles Brewton House, the Nathaniel Russel House, and the Calhoun Mansion.

Miles Brewton House

The Battery & White Point Garden

The end of the peninsula on which Charleston sits is The Battery, former home to, you guessed it, tons of cannons (some of them are still around!) White Point Garden provides a great resting spot, if you've walked here through the historic homes, to just take in the water and the festivities!

The Battery, Charleston

​If you continue from the park up Battery Street, you'll pass yet more of the city's incredible stately homes.

Battery Street, Charleston

Extra credit: Fort Sumter

Hop on a boat and tool out to Fort Sumter, the current national park and former Federal fort upon which Confederate forces fired​ on April 12, 1861, beginning the American Civil War.

If your historical facts are a bit rusty, check out Ken Burns' The Civil War, the best documentary about the conflict you can find!

Rainbow Row

Another of Charleston's famous residential areas is Rainbow Row, the first of the Georgian houses date back to the mid-18th century.

Why the bright colors on Rainbow Row?

"Many have speculated over the true reason for the color transformation of Rainbow Row. One theory is that the homes were painted various pastel colors so that drunk sailors might find their way home easier. Others believe that the various hues were the merchants’ way of indicating what types of items they sold there. One other theory is that the homes were painted lighter colors to keep them cooler during the hot Charleston summers." From Charleston.com.

Old Exchange & Provost Dungeon

If Charleston's Revolutionary history peaked your interest, stop by Charleston's Old Exchange and Provost Dungeon, completed in 1771, and one of the remaining 4 buildings in the U.S. where our Constitution was ratified.

Pineapple Fountain

Waterfront Park is home to Charleston's now-famous pineapple fountain, where it's been a staple since its installation in 1990! And, unsurprisingly, the park offers stunning views of the water!

​A Weekend in Charleston: Dining & Drinking

Seafood dinner: The Ordinary

For your "fancy" evening out in Charleston, consider The Ordinary - with incredible food and an excellent ambiance. The perfect combination of elegance and relaxed Southern vibe. Oh and perfect, fresh seafood, but in Charleston, that goes without saying.

Lunch near the water:
​Amen Street Fish & Raw Bar

If all this walking around has you craving a Bloody Mary and some fresh seafood, check out Amen Street Fish & Raw Bar on E. Bay Street. Delicious lunch offerings, and great bar offerings make for the perfect mid-day break from a busy day of touring!

Lunch on King's Street: Virginia's on King

Virginia's on King offers classic Southern fare and plenty of sweet tea if you need a rest from your day out shopping on King Street!

Extra Credit: Visit a Plantation

Just outside of Charleston are a number of gorgeous plantations. Check out this excellent guide to Charleston's plantations for a few ideas (I enjoyed Boone Hall, myself!)

Thanks for stopping by!

I hope you enjoy Charleston as much as we always do! Let me know your favorite spots in the comments below, and don't forget to sign-up for the blog newsletter!

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