I’d like to start off by saying that I could have easily spent more time in Charleston, and am already eager to return. It was rainy, cold, and dismal both days that I was there, and yet there was so much to enjoy in the city that we were able to appreciate the clouds and rain-soaked streets as dramatic backdrops in breathtaking photographs of this historic town.

So how should you maximize your time in Charleston? Here, I will share with you our itinerary, what we recommend, and what was not worth the time or expense.

We start the clock with a brunch at Toast of Charleston

Quaint, picturesque, and tucked inside a beautiful blue building, Toast of Charleston is a “must eat” if you are ever in town!

This New York Times acclaimed restaurant is famous for its delicious breakfast, and with good reason! Serving up classic southern fare, you can find everything from chicken and waffles to stuffed French toast!

And let’s not forget about the most important aspect of any good brunch: mimosas! For only seven dollars a glass, the restaurant offers several different options for a “wet” brunch. for a more cost efficient option, be sure to get the carafe of mimosas for only $20; this carafe was more than enough for two people, as we each were able to have 3 1/2 glasses! We got the Hawaiian Mimosa, which is a delightful shade of aquamarine and is made using rum, pineapple juice, blue Curaçao, and bubbles to serve up a double dose of alcohol to start your morning off right!

Our server, Shelby, was absolutely fantastic, and gave honest recommendations for his favorite items on the menu! He highly recommended the sweet tea chicken biscuit for breakfast, which was second only to his much-beloved shrimp and grits (which I ended up ordering). The shrimp was seasoned to perfection, with just enough of a spices to make it interesting. It was also paired with a healthy heaping of fire roasted vegetables and delectable andouille sausage, served on a bed of creamy grits. Absolutely fantastic, and a fantastic interpretation of a classic southern dish.

All in all, Toast of Charleston is a must visit!

Be sure to wear comfortable shoes, because you will be walking everywhere!

From Toast, we went to the Historic Charleston City Market. Although many tables were left empty and bare due to Covid, we were still delighted by the vendors who did show up! One of my passions is buying from local artists and artisans, and there is certainly an abundance of these in this iconic marketplace.

Due to COVID-19, the market unfortunately has limited hours from 9:30 AM to 5 PM, so be sure to plan your visit between these hours if you want to go! Masks are currently required inside of the market at all times, but there are plenty of spaces to go outside and take a breather if masks make you feel stuffy.

The market is packed with unique souvenirs of this iconic city; from sweet grass baskets that were historically used to winnow rice on local plantations, to vibrant Van Gogh-esque paintings that capture the magic of the city, there is a little something here for everyone. Spanning the length of several blocks, one could easily spend several hours exploring the different kiosks and booths in the Charleston city market.

This building has been around for nearly 200 years, and has earned a place as a permanent exhibit entitled “Life in Coastal South Carolina c. 1840” in the American History Museum in the Smithsonian Institute in Washington, D.C.!

I was very pleased to find a local artist here who sold her original paintings for and astonishing price of only $60! Using vibrant colors, thick acrylics, and sweeping brush strokes, her paintings embody the vibrant atmosphere that Charleston is known for today. I’ve never been quite so happy to buy a painting in my life!

This talented artist, Sofya Tsvetikova, hails from Russia and moved to Charleston over 20 years ago, inspired by the unique architecture, colorful neighborhood, and vibrant nightlife. She offers everything from prints and handpainted magnets to original paintings both large and small. With a thriving presence on Instagram as @PaintingCharleston, she told me that her original paintings frequently sell out online due to their relatively low pricepoint and incredible quality. I felt extremely lucky to have met her and to purchase one of her paintings in the city market! You can find out more about Sofya on her website or on Instagram.

Continuing through the market, you will pass stalls that sell everything under the sun, from sweets and locally-roasted coffee beans to spices, candles, jewelry, clothing, and kitchy souvenirs! Peppered throughout the market are several food stalls with delicious smells to entice even the most resilient passer-by. You will want to have some cash in hand if you plan to do any shopping, as several of the craftspeople and businesses do not accept credit cards.

A stroll through the market is an entry into another world, a place to experience Charleston’s true Southern charm and bear witness to the artists who capture the essence of Charleston.

Travel back through time through philadelphia alley

This alley is often neglected by tourists and, for the majority of the time, remains eerily quiet and devoid of human intrusion. While this alleyway may seem like private property, it is in fact open for visitors and residents alike to come through and experience a quiet solitude from an otherwise bustling city.

We nearly passed this alley on our way to the riverbank, but as this city is wont to evoke, the charming cobblestones and wrought ironwork that marks the entrance caught my eye and had me whipping out my camera before I even knew what was happening. Passing beyond the iron gates, I felt as giddy as an archeologist who discovers a lost city. The alley, untouched by the 21st century, oozes provincial charm and evokes that wonderful sadness brought on by ruins and abandoned things.

You can find this hidden gem tucked between Cumberland Street and Queen Street, and you wouldn’t know it was there unless you were looking for it!

Enter the world of the Greatest Showman at the dock street theater

If you turn right from Philadelphia alley onto Queen street and then take a left on Church Street, you will find yourself staring down the impressive facade of the Dock Street Theater. Built in 1809, this impressive building has an interesting history and has several accolades to its name, including the first building built exclusively for theater in the United States, occupying the plot where the first theater in the Colonies once stood, and played host to the first Opera held in America.

It once was transformed into the Planter’s Hotel, a glittering jewel for Charleston’s high society to gather, and was the birthplace of Charleston’s famous Planter’s Punch, which you absolutely must try at any local bar in town!

Experience charleston’s dark past as a slave port through a visit to the old slave mart museum

Charleston has done an excellent job of owning up to its sordid history and recognizing its role in the slave trade. The Old Slave Mart Museum is actually housed in the building that once served as the showroom for slave traders, and for a small fee, you can tour the building and read about the experiences of enslaved individuals who found themselves being traded in Charleston.

In my personal opinion, the Slave Mart Museum does not do a great job with engaging its patrons; the displays completely conceal the building itself, and it is completely self-guided, with enough text to fill a book about the Charleston Slave Trade. Housing very few artifacts and relying mostly on stories and expansive text to discuss the history of the slave trade in Charleston, it was ultimately an un-engaging experience.

I recognize that there is a need to appreciate the somber realities of the slave trade in Charleston, and to be mindful of those who still feel the impacts of slavery today. However, I believe that there is a way to go about it that truly engages while also evoking a sense of respect and (dare I say) horror at the atrocities committed not so long ago.

Take, for instance, the Holocaust Museum in Washington, D.C. – while remaining reverent to the lived experiences of those who suffered through such an ordeal, the museum leaves a lasting impact on those who go through it, from the multimedia exhibits to giving each patron an “ID” card of an actual Jewish victim of the Holocaust.

I appreciate what this museum tries to accomplish, and I wish that there had been more effort committed to making it a truly impactful experience so that those who go through the museum appreciate and empathize with the plight of those who were enslaved.

Take a photo with the famed pineapple fountain at the Joe riley waterfront park

Head East back down Queen Street if you want to see the iconic Pineapple Fountain that you always see photos of! The street ends with lovely shops and buildings lining either side of it before becoming the waterfront park.

Pineapple motifs are common in Charleston (and in historic Southern towns in general) primarily because it represents hospitality! You will frequently see pineapples adorning doorframes, fountains, door knockers, and more!

The pineapple also gained popularity as a symbol of the city because of its use by ship captains who, arriving back home from trading in South America and the tropics, would hang a pineapple outside their door to announce their return to the neighborhood! From there, the pineapple quickly transformed into a piece of decorative art, immortalized by artists and becoming a symbol of status, wealth, and eventually, hospitality. After all, what is more hospitable than sharing your hard-obtained pineapple with a guest?

This particular (and iconic) Pineapple Fountain was built after Hurricane Hugo swept through Charleston in 1990.

Be sure to stop at Belgian Gelato for a delicious cup of gelato before heading to the river – and don’t worry if you’re lactose intolerant (like me): they have several absolutely delicious dairy-free offerings for those of us that can’t handle our dairy!

In the summer, you can actually play and splash about in the fountains scattered throughout the waterfront park, so be sure to plan your visits for a sunny day so that you can unleash your inner child! As for when I visited (late February), it was rather cold and rainy, so not quite ideal for a dip in the fountain.

Regardless, the area does not lose its beauty even in inclement weather, and remains a must-visit spot for your visit to Charleston!

Stroll down E battery street to see rainbow row and other historic (and colorful) charleston mansions

Perhaps the sight that Charleston is most well-known for, Rainbow Row adorns Charleston souvenir magnets, mugs, paintings, postcards, and more. These pastel-colored Georgian houses will spark your creativity (and possibly make you green with envy), and serve as the perfect backdrop for a photo to make all your friends jealous.

Continue South down E Bay Street until it turns into E Battery Street for a lovely riverside stroll to see more breathtaking mansions that were practically all funded by the work of enslaved people (a sobering thought when you start to take in just how grand these mansions are). Eventually, you will reach the Edmonston-Alston house on the right. For a small fee, you can take a tour of this gorgeous house and get a taste of what the good life looked lack back in the 19th century before slavery was ended.

The house is actually still occupied by one of the original owners, who resides in the topmost level of the house – as guests, you are able to tour the first and second floors of the house, with the opportunity to walk out onto the sweeping balcony to face the river. I highly recommend taking advantage of this tour if you are at all curious about the interiors of these elaborate mansions!

Love shopping? Then King Street is the place for you!

Lined with popular chain stores, local boutiques, and local artisans, a stroll down King Street will satisfy the shopaholic in you, and give you an abundance of opportunities to shop small and help bolster the local economy!

The shops that I recommend the most are Savannah Bee Co. and Candlefish! But there are plenty of other shops to entice your wallet, offering an eclectic variety of items for you to peruse.

Savannah Bee Co is a brand local to the south, and offers everything from raw honeycomb to mead, from flavored honeys to delicious whipped honey! They have a tasting bar inside, where during normal times (but not during corona, unfortunately), they offer tastings of everything from their wicked honeys to the meads that they produce.

Candlefish is also in a unique experience that you can only find in Atlanta and Charleston! In the Charleston shop, you can book time to make your own candles with them, or visit their library of fragrances to discover new and delicious scents! The cool thing about the library is that all one hundred of the fragrances are numbered, so the name of the fragrance doesn’t sway your opinion or expectation in any way. The talented shopkeepers have memorized every single number, and can provide a personalized experience for your smelling pleasure.

My absolute favorite shop on King Street, however, is 7 Hills Living, an eclectic home decor store that transported me back to the souks of Morocco, complete with hand woven rugs, glittering lamps, and unique fixtures for your home! The space has been designed to capture your eye and awaken a sense of wonder, filled with such items as are meant to dazzle every patron who enters.

I could have easily spent much longer in this shop, for they had so many items to catch your eye and dazzle your senses, including handmade leather bags, handwoven rugs, gorgeous woven shawls, hand-beaded necklaces, and gorgeous lighting covers and lamps!

There is one room in the shop that is completely filled from floor to ceiling with Moroccan-style lamps, and it made me miss Morocco from the depths of my soul. I have never expected to find a shop such as this in such a southern town as Charleston, but if you ever want to have a small taste of what Morocco is like, visit this shop!

After a full day of exploring, nothing tastes quite as good as some classic Southern barbeque

Unfortunately, I didn’t take any photos of this place, but only because we were so occupied with the delicious food in front of us! If you truly want a taste of the south, there is nothing so quintessentially southern has good barbecue and tender brisket.

We went to Lewis barbecue on N. Nassau St., an unassuming building that is primarily only known by locals, but is beloved by all who try it!

The mark of a good barbecue place is not the barbecue itself, but the quality of the brisket! Any old fool can pull apart some pork and season it until it tastes good enough, but brisket is a more stubborn cut that requires more patience and skill to cook than you might think. Luckily, Lewis holds up to the standard that I have for good brisket: The edges are perfectly crispy and seasoned, and the interior is so tender that it falls apart on the fork, a classic mark of an excellent brisket.

Sold by the pound, don’t be put off by the cost! You can buy your meal in any increment that you want, and a half pound of the brisket was, quite honestly, more than enough for me – I wasn’t even able to finish all of it! Additionally, the mac & cheese is absolutely fantastic, and the fries are, dare I say, even better than Bojangles!

Start off Day Two right with brunch at Poogan’s Porch!

We headed back into town the next morning, eager to experience another option for brunch. While toast made such a positive impression, we truly wanted to see if any place could match up to the quality of toast, and we didn’t have to look far!

Located on Queen Street, Poogan’s Porch is a restaurant held inside a gorgeous two-story historic house, built in 1891! In Charleston, it is not rare to throw a rock and strike a restaurant that has garnered national recognition, and Poogan’s Porch is no exception: Charleston‘s oldest independent culinary establishment, Poogan’s Porch has been recognized by Martha Stewart living, southern living, and the Travel Channel!

The restaurant got its name in a rather unusual way; once owned by a pair of sisters, the family eventually sold the house to the aspiring restaurant owners who, unbeknownst to them, also inherited the responsibility of caring for the local neighborhood dog who claimed Lot 72’s porch as his home. He soon became a guardian of the fledgling restaurant, observing the restoration of the building from his beloved porch and greeting every patron with a wag of his tail when the restaurant finally opened. He became an icon, an institution of the restaurant, and having died a natural death in 1979, the restaurant now stands as a monument in his honor.

We didn’t know any of this, but enticed by the smells coming from the building, and charmed by the gorgeous exterior of this historic house, we found ourselves seated on the second floor dining room of the restaurant.

I was delighted by the classic southern fare offered on the menu, with too many choices to ever truly settle on just one! Offering everything from shrimp and grits to fried chicken, Poogan’s Porch has skillfully married the classic southern tradition with the seafood fare that Charleston is known for.

I finally settled on the chicken and waffles, which is served with blueberries and a deliciously sinful sorghum butter. As many of you may know, I have a particularly reverent view of chicken and waffles, being from the south and frequently dining at what is arguably one of the best joints for chicken and waffles in North Carolina (Beasley’s in downtown Raleigh – you MUST try it!).

There are a few places that meet my high expectations for this quintessential southern brunch dish: metro diner in Columbus, Georgia; Beasleys in Raleigh, North Carolina; and now Poogan‘s porch in Charleston South Carolina! I don’t know what they put into the breading on the chicken, but I felt like I died and gone to a Martha Stewart heaven!

I refused to let any of it go to waste, knowing that we were leaving soon after to head down to Savannah, so we stayed at that restaurant until I was able to down the entire thing!

Love spooky vibes? Head down to the Old Charleston Jail

Now, I don’t recommend ending your trip on this note, primarily because you cannot enter the old Charleston jail without being part of a tour group, and currently the city is only allowing nighttime haunted tours of the jail. That being said, if you’re pressed for time like we were, even just walking around the outside of the jail is enough to send a shiver up your spine!

This spooky old jail can be found on magazine street, and was in use from 1802 up until 1939! The jail played host to many notable figures, including union officers during the Civil War, high seas pirates, Denmark Vesey (who led the slave revolt of 1822), and Lavinia Fisher, the United States’ first female serial killer!

One of the only buildings in Charleston to have been looked over for restoration, this jail stands as a testament to the past, and what happens when we don’t actively preserve it. The next time I go to Charleston, I am making a point of booking a nighttime haunted tour of the Old Charleston Jail!

Have you ever been to Charleston? Did I miss any notable sites, restaurants, or activities? Feel free to reach out to me on Instagram @lifeofbusynothings, or via email at kristinmarie@lifeofbusynothings.com!

Coming soon, 48 hours in Savannah, Georgia!