City Break: Charleston

By Amanda Wowk

March 15, 2023

City break (noun): a short holiday spent in a city, such as when on business travel.

Before there was bleisure travel, there was the city break—the short space of leisure time that grants you access to the cultural and culinary amenities that big cities offer. In this series from TripIt, we explore some of the world’s best cities for planning a quick getaway or extending a work trip.

Here are our tips for making the most of your city break in Charleston. 

Where to fly in

Charleston is served by Charleston International Airport (CHS), located just 12 miles north of the city. CHS consists of one main terminal, with flights departing from two concourses. While it is South Carolina’s busiest airport, it’s also relatively small, and thus, easy to navigate. 

Once on the ground, travelers can catch the Charleston Area Regional Transportation Authority (CARTA) public bus service right outside of baggage claim to head into the city. CARTA’s Airport Express route is a direct link between the airport and downtown Charleston. 

Taxis and ride shares are also available from CHS. Alternatively, rental car pick-up can be found just past baggage claim before you exit the terminal.

Where to stay during your city break


In search of some Southern hospitality? Look no further than the colorful The Mills House Wyndham Grand Hotel. Here, you’ll stay in the heart of Charleston’s historic district, steps away from fine dining restaurants, vibrant nightlife, and charming shops. 

The Dewberry oozes sophistication and warmth. Guests will enjoy its many amenities, including The Living Room—open for breakfast and again for evening cocktails and dinner. 

If a hotel in a prime Charleston location is what you’re after, look no further than the Andrew Pinckney Inn. This four-star hotel is walking distance from major attractions such as Waterfront Park, Charleston City Market, College of Charleston, and more.

Looking for the charm of a boutique hotel? Check out—well, check in—to Emeline. Located in historic downtown Charleston, this hotel is a great place to call home while you explore the city. Grab a coffee from on-site coffee shop Clerks before you head out; return in the evening for a glass of wine on the patio. The twinkly lights await you. 

The Ryder Hotel, another boutique hotel located downtown, is easy walking distance to all of the city's major sites (more on what to do, below). Come for the fresh and fun design, stay for the drinks at Little Palm—the hotel's on-site bar and restaurant. Guests will also be pleased that morning coffee and espresso bar drinks are included in the resort fee. Have time for breakfast? Enjoy a $30 breakfast credit every morning at Little Palm. 

In Charleston on business and in need of event space? The Francis Marion Hotel offers 19,000 square feet of meeting space, including a conference center. Business travelers will also appreciate the complimentary Wi-Fi, on-site business center, and express check-out. 

How to get around


Part of Charleston’s charm is its easy walkability. Plan accordingly by packing comfortable shoes for walking from place to place. Your reward? An unobstructed view of Charleston’s colorful homes, complete with tucked-away piazzas and decorative flora.  

When walking isn’t feasible, Charleston’s CARTA bus system can be your go-to for getting around. An express one-way fare costs $3.50 and can be purchased online or from the bus driver (exact change only). Alternatively, a day pass costs $7; multi-day passes are available at a reasonable discount, as well.

You can purchase individual trip and ride passes on your phone, and use that digital pass to board the bus using the Token Transit app. Transit passes are also available at the Charleston Visitor Center. 

Alternatively, Uber is available in Charleston and is likely your best option for getting around the city in a jiffy. 

Pro tip: Use TripIt’s Navigator feature to search transportation options available to you. It will show you the estimated costs and travel times for each option, so you can decide which works best. You can find Navigator within your flight, hotel and rental car details screens. Plus, if you add a restaurant reservation to your itinerary (more on where to eat below), Navigator also helps you find the best transportation options for getting to your table.

Where to eat

city break Charleston

If you traveled to Charleston just to eat at its restaurants, I can’t blame you. A city known for bringing together the flavors of the Lowcountry—both from the land and the sea—Charleston is guaranteed to satiate any kind of appetite. 

If you only have time for one meal in Charleston, make it at Husk. This award-winning restaurant features seasonal dishes made with locally-sourced ingredients. You will absolutely need a reservation (seriously, make one now, I’ll wait…). Didn’t snag one in time? Bide your wait at the bar enjoying a classic cocktail, or opt for a specialty drink crafted by Husk’s professional mixologists.   

Just a few doors down on Queen Street, 82 Queen is another delectable option for fine dining in Charleston. Aimed at celebrating all the Lowcountry has to offer, 82 Queen is open for lunch, brunch, and dinner. 

In the mood for Japanese cuisine? Make a reservation at 167 Sushi Bar (yes, you'll need one). Here, the sushi and the service shine.  

Have a new client (or a new date) to impress? Book a table at Maison. This French restaurant offers a seasonally inspired menu and a $5 champagne happy hour. Win-win? Oui!

Craving Southern BBQ in a casual atmosphere? You came to the right city. Choose from delectable spots like Rodney Scott’s BBQ, Lewis Barbecue, and Home Team BBQ

Need something light(er) for lunch? Head to Circe's Grotto for salads, sandwiches, and more—and enjoy your food al fresco on the charming outdoor patio.

What to do on your city break

city break Charleston

If this is your first time visiting Charleston, start your clock at Charleston City Market. Take a stroll through the great hall and open air sheds—some dating back to the early 1800’s—that now house local vendors selling crafts and goods. 

Once you’ve had your fill of the market, board a horse-drawn carriage for a tour of the city. During your one-hour tour, you’ll learn about the city’s history, and how earthquakes, great fires, and two wars have shaped its evolution. Carriage tours can be picked up right next to City Market. If you only have one hour of leisure time in Charleston, I highly recommend you spend it here.

There are also plenty of kid-friendly things to do in Charleston. Catch the ferry to Fort Sumter to learn about its place in American history, particularly the role the fort played in the Civil War. Or, head to Folly Beach, about a 25-minute drive from downtown, for some family fun in the sun. 

Adults only? By day, wander King Street and Queen Street to shop the city’s many art galleries, as well as many luxury and boutique shops. Looking for a refresh after all that walking? Book a spa appointment at The Dewberry Spa.

By night, head to The Gin Joint for unique handcrafted cocktails, interesting wines, and light bites. Or, sample locally made wine at Charleston Wine Co.—the city's first urban winery. It's located just steps away from City Market.  

Looking for a different kind of spirit? Book a ghost tour with Bulldog Tours for a guided jaunt through the city’s graveyards, jail, dungeons, and more.