Charmed By Charleston: A Getaway To The Holy City

“I’m going back to Charleston, where there’s still a little grace and civility left in the world.”

So says Rhett Butler to Scarlett O’Hara in Gone with the Wind. Over 80 years after these words premiered on the big screen, these qualities can still be found in the charms of this Southern port city, and modern-day visitors find it just as easy to fall in love with Charleston’s historic cobblestone streets, pastel-colored houses, and elaborate wrought-iron fencing.

Known as the “Holy City” for the impressive number of churches it houses (over 400 at last count), Charleston, South Carolina, is the most visited city in the United States every year. With its rich offerings of good shopping, better food, and an authentic, laid-back atmosphere, Charleston welcomes visitors to stay and admire the elegant features of the days when it was the largest and wealthiest Southern city, as the hub of Atlantic trade in the colonies. It is the classy elder counterpart to its sassy sister city, Savannah, Georgia, a two-hours drive away.

With so much Southern charm for visitors to experience, Charleston would be difficult to try to experience fully in just a weekend – which makes it easier to plan on returning for future visits! Here are a few of the highlights of our favorite things about Charleston:

EAT + DRINK CHARLESTON

To tell you the truth, there is no wrong choice when it comes to food and drink in the Holy City. Charleston boasts a truly impressive selection of excellent restaurants, delis, bakeries, taverns, distilleries and breweries. You can sample any flavor imaginable somewhere within walking distance. But my favorite part of eating around Charleston is the seafood – there is something about being situated next to the water that makes eating a hamburger feel like a betrayal! Some of our favorite dishes are shrimp & grits, oysters on the half shell, and the she-crab soup.

There are so many choices, you could spend at least a month in the city and never eat at the same place twice. Just be aware – it’s usually easy to snag a seat at most restaurants for breakfast or lunch without a lengthy wait, but dinner is a different story. Be prepared to wait an hour or more if you don’t make reservations ahead of time.

Here are just a few of our favorite spots:

• Located in a yellow Victorian two-story home on Queen Street, Poogan’s Porch serves traditional Southern fare. We especially enjoy their Pimento Cheese Fritters – think of crispy balls of hot pimento cheese goodness. The venue is named after a beloved neighborhood stray who made himself at home both before and after the restaurant opened its doors. It is said that Poogan’s ghost as well as the spirit of the home’s last resident are still seen occasionally by patrons and staff.

• Some of the best seafood we ate in Charleston was at Hyman’s Seafood, which always has a line of hungry patrons waiting to dine. We were originally warned about the restaurant being a “tourist trap”, but there is a reason for those long lines – the food is delicious and plentiful, and the service was the friendliest we received during our visit. Each seat at the table has a brass plate with the name of a celebrity who sat there before you. It was truly our most enjoyable meal in Charleston!

• If you’re craving pizza, Benny Ravello’s on King Street has you covered. Their pizzas are enormous, with slices at 14 inches long!
• My favorite thing to eat when visiting Charleston is oysters on the half shell. Granted, they can pretty much taste the same, depending on the type you order, at just about any oyster bar in town. Charleston has dozens of oyster bars to choose from – and they are all very good. This trip included visits to Rappahannock Oyster Bar, Oyster House, Pearlz Oyster Bar and Amen Street Fish & Raw Bar.

• For drinks, we recommend Prohibition, for its 1920s-speakeasy vibe and interesting versions of classic cocktails. You may come for the drinks and stay for the dinner – they serve Southern fare in creative ways.

• Located on busy King Street, Miller’s All Day is a great little spot for brunch. We really enjoyed the vintage vibe of the place. We shared the Millers Smash Burger and the Nutella Cream Filled Donut for dessert.

• Our hotel concierge recommended Fleet Landing on our first evening there, and it did not disappoint! The shrimp & grits are excellent. Try to get an outside table if you can for a view of the harbor.

EXPLORE CHARLESTON

There is no shortage of things to do in Charleston, from touring Fort Sumter where the Civil War began, to watching the sunset from the harbor in your rented sailboat. No matter what interests you, it is guaranteed you will never be bored in the Holy City.

Here are a few of the fun outings we enjoyed (and some of them are free!):

• One of the best sources for the history of Charleston is a tour of the Old Exchange and Provost Dungeon, which was once a grand custom house that greeted merchant ships as they brought their goods into port. Built in the 1760s, it is one of the most historically significant colonial structures in the entire country. The Exchange saw the Declaration of Independence read for South Carolina citizens, after which it was used as a prison by the British during the American Revolution. In 1790, the State Legislature met in the upper rooms to ratify the new Constitution, and George Washington himself hosted events here in 1791.

• Stroll down Concord Street to the 10-acre Waterfront Park to take in the fantastic views of the Charleston Harbor and the Cooper River, and to visit Charleston’s now-famous pineapple fountain. The pineapple is a symbol of hospitality and friendship that goes back to the days of seafaring shipping merchants, who were known to hang a newly imported one outside their homes upon return from maritime pursuits, to broadcast that they were home from their travels and available to socialize.
• One of our favorite things to do is wander around Charleston’s historic districts and discover the hidden alleys and courtyards near houses that were built colonial times. Be sure to take note of the homes featuring plaques that indicate the historical significance of the structure. The stringent rules of the Preservation Society of Charleston assures that each home is carefully preserved exactly as it was when it was constructed, and the authenticity and beauty of the historic dwellings is impressive.

• For a must-do Instagram photo-op, head over to Rainbow Row, a cluster of pastel-hued Georgian-style row houses that used to be waterfront warehouses dating back to well before the Revolutionary War. These are private homes, and are not open to the public, so please be respectful when taking photos.

• A visit to the Battery is a must while in Charleston. It is located on the tip of the peninsula of the city and served as a defensive seawall during the Civil War. Make time to stroll through White Point Gardens, and admire the stately waterfront mansions and the fantastic view of the meeting of the Ashley and Cooper Rivers.

• Step back in time and tour one of the stately Federal-era mansions that are now open as public museums. The Aiken-Rhett House was built in 1820 in one of Charleston’s historic neighborhoods and has been home to a railroad magnate and a South Carolina governor. Tour the estate and outbuildings of the Joseph Manigault House, built in 1803 for a wealthy rice planter and French Huguenot who came to America to escape religious persecution. You can also visit the home of a signer of the Declaration of Independence at the Heyward-Washington House, where George Washington stayed during his visit to Charleston in 1791.

• A city as old as Charleston is sure to be home to a few ghosts. Take an evening stroll on the Death and Depravity Ghost Tour and enjoy the spooky side of the Holy City!
• One of the best ways to visit a city for the first time is on a carriage tour. You get to see a good portion of the city while resting your legs. Our guide with Carolina Polo & Carriage Company kept it interesting by telling colorful stories of Charleston’s past and giving helpful sightseeing advice, so take note of spots your may want to come back to later.
• Although there are several plantation tours to choose from, we opted to visit Magnolia Plantation & Gardens just outside of Charleston. Established on the Ashley River in 1676 by Thomas and Ann Drayton, Magnolia Plantation is said to be the last large-scale romantic-style garden in the country. We spent half a day wandering the garden paths and admiring the vast varieties of flowering plants, including azaleas, magnolias, daffodils, jasmine, wisteria, camellias, and many more. The more adventurous visitor can add a swamp tour to your visit.

SHOP CHARLESTON

Charleston has a ton of boutiques, galleries, and specialty stores sprinkled everywhere throughout the city. You can lose yourself (and your cash!) for hours in a spending spree in what is often considered one of the best shopping spots in the world.

• The historic Charleston City Market is a national landmark that houses over 100 vendors selling their wares seven days a week. The Market, which has been in operation since 1807, stretches over 4 city blocks and serves as the cultural hub of downtown Charleston. You can purchase everything from snacks and pastries to traditional artwork and sweetgrass baskets from local craftsmen.

• You will smell the incredible scent of Market Street Sweets (its sister store is in Savannah!) from a block away. Be sure to stop in and taste their fresh pralines. You will thank me later.

• Charleston’s iconic King Street is over 300 years old and remains the city’s main shopping district. It’s a must-do if you enjoy browsing trendy boutiques, from antiques to fashion to art and design. My favorites were Blue Bicycle Books and Oops! Clothing. Many of the popular restaurants call King Street home as well.

• Enjoy the history of Charleston’s architecture? You can shop the Historic Charleston Foundation, whose shops feature exhibits that showcase the city’s architectural history. They offer a large selection of books on Charleston and its culture, architecture and history, as well as unique 18th and 19th-century reproduction furniture, jewelry and gifts.

This list is only a sampling of the many things Charleston has to offer its visitors. Charleston will always be a place we love to visit, and we are looking forward to our next trip. It’s truly a unique and beautiful city, and there is always something fun to do, whether it’s eating our way through the city, exploring the scenic neighborhoods, or enjoying the downtown vibe.

P.S. We stayed at the historic Ansonborough Inn, which was a treat, and deserves its own feature on the blog. You can read about our stay in this historic hotel here!

Want to experience Charleston for yourself? Check out Explore Charleston to get all the details you need to plan your trip.

What is your favorite part of visiting Charleston? Tell me all about it in the comments!

* I’m aware that these uncertain times are limiting many aspects of life as social distancing remains a reality. While this blog will continue to feature destinations to explore, use your own discretion when deciding whether or not to travel and please respect all local guidelines. I believe that supporting local attractions is important now more than ever and I hope these articles inspire your future adventures! Also, this post may contain affiliate links. If you make a purchase through them, I may receive a small commission (for which I am deeply grateful) at no cost to you.