Skip’s Favorite Things to Do & See in Charleston

As a Licensed City Tour Guide, I like to think that I am uniquely qualified to make recommendations to anyone planning a Charleston vacation. For those of you who have never visited my website before, I am also a Charleston native—one of five generations—which means I have personally experienced most of what our fair city has to offer.

Every now and then, folks reach out to me through my website when planning a trip, but most of the time, I don’t get to interact with guests until they are already in Charleston and on one of my walking tours. I am always thrilled to meet folks on their first day in town, when their Charleston experience is still a blank slate bursting with possibilities. I like getting to know people and making personalized recommendations. I hope you will book a tour with me when you visit so you can see what that’s like, but for those who like to pre-plan, I’ve put together a list of my favorite things to do in Charleston to get you started.

Things to Do & See in Charleston

1. Eat – Charleston’s culinary scene is top-notch. As far as entertainment goes, eating definitely tops the list for locals and tourists alike. Here are a few of my favorite dining destinations in downtown Charleston…

• For Lunch: Eli’s table, Cru Café, Mills House, Husk, Poogan’s Porch, Brown Dog Deli, and Fleet Landing
• For Dinner: Hall’s, Hank’s, Oak, Slightly North of Broad, Peninsula Grill, Magnolia, and Blossom

2. Take a Tour (or Two or Three) – Tours are an excellent way to see the city. The following tour companies offer experiences that are substantive, entertaining, and quintessentially Charleston without being overly touristy.

• History Tours: Walking Charleston That’s me! I offer a general history tour, a Civil War history tour and private walking tours.
• Carriage Tours: Palmetto Carriage Tours
• Ghost Tours: Charleston Haints and Hoodoo Tours
• Historic Site Tours: Ft. Sumter Tours

3. Plan a Plantation Excursion – Even if you plan to stay in Charleston’s Historic District, I highly recommend seeing at least one Charleston area plantation. My favorites are Boone Hall (Mount Pleasant), Middleton Place (West Ashley), and Magnolia Plantation (West Ashley).

4. Visit a Historic House – Charleston has several historic houses that are open year-round, and I highly recommend docent led tours at the Nathaniel Russell House, the Heyward Washington House, and the Aiken Rhett House.

5. Take a Waterfront Stroll – No vacation in Charleston is complete without a waterfront stroll. Be sure to visit White Point Gardens (at the corner of Murray and East Battery). From there, you can take a walk along High Battery (paralleling East Battery) to catch a glimpse of Fort Sumter and Castle Pinckney. Joe Riley Waterfront Park (at the corner of Concord and Vendue) offers an equally iconic experience, as it is home to the famed Pineapple Fountain as well as a wading pond on the north end of the park. It’s hard to believe that Waterfront Park has only been around since 1990. It opened the spring following Hurricane Hugo, and the Pineapple Fountain quickly became Charleston’s grandest symbol of hospitality. As such, it is only fitting that the the park welcome waders. In fact, the City of Charleston both expects and encourages guests to get their feet wet… So if you visit on a warm day, dress accordingly.

6. Shop for Something Special – King Street is a popular shopping destination and offers a variety of major retailers and lesser known boutiques (mostly clothing). For gifts, keepsakes and Charleston souvenirs, I recommend The Historic Charleston Foundation Shop (108 Meeting Street), King Street’s Antique District (Lower King Street) and the Charleston City Market (commonly mis-represented as the “Old Slave Market”).

7. Appreciate the Arts – The Gibbes Museum of Art features more than 10,000 works of fine art, most of which are by American artists with many having a direct connection to Charleston. The first floor of the Gibbes Museum is open to the public Tuesday-Sunday, and admission is completely free. A ticket is required to view installations on the second and third floor. Tickets, which range from $6-15, can be purchased online. While the Gibbes Museum is Charleston’s only official visual arts museum, Charleston is home to an array of galleries. My favorites are the John Doyle Gallery (125 Church Street) and the Charleston Artist Guild Gallery (160 East Bay Street).

8. Entertain the Kids (or Your Inner Kid) – Joe Riley Waterfront Park is a home-run hit for kids of all ages. For indoor, family-friendly entertainment, I recommend visiting the Charleston County Museum and the SC Aquarium.

9. Step Back in Time (or into Colonial Times that Is) – Settled in the 1670, Charleston got it’s start as a colonial seaport. For remnants of what colonial Charleston looked like (1670-1779), I recommend visiting the Colonial Powder Magazine (SC’s oldest public building located at 72 Cumberland Street) and the Exchange Building (a colonial civic structure located at East Bay and Broad). 

10. Imbibe – After a day full of exploration, there’s nothing better than a leisure evening. Building restrictions have kept Charleston’s unique skyline intact, and rooftop bars offer an unobstructed view of the Holy City and Charleston Harbor. My favorite spots for an evening cocktail are The Pavilion Bar at Market Square Pavilion and The Rooftop Bar at Vendue.

The Rooftop Bar at Vendue, Photo from Facebook 

You should be able to fit most of those activities into a long weekend, but try not to over-schedule yourself when planning your Charleston vacation. Leave ample time for walking and wandering.

Charleston is an increasingly popular travel destination, with spring being the busiest season. As such, be sure to make hotel and dinner reservations early. Lunch reservations are often a good idea as well. Be sure to leverage the help of your hotel concierge to assist with planning.

Spring events and fall festivals lure in large crowds, but Charleston has plenty to offer in the summer and winter months as well. For an up-to-date listing of what’s happening, check out the CVB calendar and HolyCitySinner.com.

I hope that you will have an opportunity to vacation in Charleston soon. When you do, please consider booking a Walking Charleston tour, and plan it early in your trip. I would love to make some recommendations of things to do and see that are based on your interests.