A Guide To Charleston, South Carolina: Warm Winter Escape

The early years

Even those who don’t think of history as a reason for choosing a place to vacation would find Charleston exceptional. In the 1700s, the American colonies were growing in size and wealth. At that time, the leader in riches was Charleston thanks to the trade with Caribbean merchants, thriving rice industry, timber, and tobacco. Locally grown rice was held in such esteem it earned the name Carolina Gold due to its high value as a cash crop. Indigo, used for dye, was also a valuable crop in the early days. Local plantations grew wealthier as new markets opened up thanks to an excellent harbor shipping goods to Europe and beyond. The slave trade was also a part of Charleston’s history until congress banned importing slaves from foreign countries in 1808.

After the Civil War, Charleston started a new era of prosperity thanks to a rebuilt industrial economy. In the 20th century, tourism began to grow by attracting visitors searching for world-class cuisine, beaches, golf, and history. The downtown area has plenty of museums, restaurants, hotels, and shopping to fit any traveler’s desires.

Where to start exploring

The best way to start your exploration of the downtown area is by taking a horse-drawn carriage ride. A variety of operators offer one-hour tours with knowledgeable guides and carriages seating up to 16 customers. The larger carriages cost about 45 USD and take you on a route decided by a bingo system. The bingo system prevents crowding in the narrow Colonial streets. After starting on the trip, your driver pulls up to a shack on Market Street where a worker picks one of five routes, then off you go.

On a recent trip our driver Bryan pointed out the curious narrow alleys, like Stoll’s Alley to explore this pathway full of flowers, historic houses, large trees, and other curiosities. Bryan was also knowledgeable on the historic homes and the ones visitors can tour. By getting your bearings on a carriage ride, you can later explore places your guide piqued your interest.

Eat it up

Downtown Charleston and the outskirts of town offer some of the best dining in the US. Most of the area’s cuisine is known as “Lowcountry” featuring favorites like shrimp and grits, hushpuppies, fried flounder, biscuits, and delicious bbq. Try one of the coveted James Beard award-winning chef’s restaurants for an exceptional taste of Lowcountry fare at Husk, Fig, Hominy Grill, and The Ordinary.

Circa 1886 restaurant is located on the grounds of the Wentworth Mansion Inn and will take diners on a tasty historical food tour. The fine-dining menu at Circa 1886 pays homage to the influences of Native Americans, Africa, Europe, and modern Southern cooking.

Visitors can find less pricey but excellent fare at Miller’s All Day Breakfast, Virginia’s on King, and Callie’s Hot Little Biscuit. If you want to mix it up and try something farther from downtown, there are numerous eateries on Folly Road, Folly Beach, and north of downtown.

Read my article on excellent restaurants in Charleston, for more information.

Deep dive into history

Start your journey at The Charleston Museum on Meeting Street, across from the visitor’s center to get the most of your historic Charleston visit. Tour the museum and learn about indigenous Americans that lived in the Low Country before Europeans came. Follow the path of the early settlers, enslaved and freed Africans, and others who gave the area the charm you see and taste today.

After the museum, be sure to go to the visitor center to get an overview of what to see and do. You can catch the free Dash Bus at the visitor center and save on walking. Rideshare options like Uber and Lyft are available but savvy travelers will benefit having both rideshare company’s app on their smartphones to compare the pricing. On our recent trip, we found that one rideshare company was as much as twice the price of its competitor!

At the visitor’s center, check out information on the plantations upriver that allow visitors. Plan to spend 2-3 hours visiting one of the plantations for a house tour, a walk around the grounds, gardens, and lunch before heading back to town. Guided house tours usually cost a bit extra but are worth it if you love historic homes. Some famous plantations to visit are Middleton, Boone Hall, Magnolia, and Drayton Hall. At Magnolia Plantation & Gardens, you can take a walk in the Audubon sanctuary to see alligators, birds, and turtles safely from a raised walkway. Don’t miss the Magnolia Plantation gift shop where you can buy paintings by Simon, the raccoon who lives in the on-site zoo. Simon was rescued from the wild and given a plush home at Magnolia, where the zookeeper discovered his painting talent.

If the weather allows, explore the extensive romantic-style gardens that reach towards the Ashley River. Romantic-style gardens of this size are rare and differ from formal gardens by blending into the natural area.

On the water

Several water activities are worth mentioning. From the Charleston waterfront, off in the distance is Fort Sumter, the famous Civil War-era fort said to have started the war that threatened America’s future as one country. You can take a ride on the Carolina Belle for a harbor cruise or go with SpiritLine Cruises to see the fort and more from the comfort of a modern boat. If you want a vintage tour on the water, the three-mast Schooner Pride is an 18th-century replica of tall ships that plied the Atlantic Ocean long ago.

Where to stay

There are so many hotels, BnBs, vacation rentals, and private homes for your trip it will make your head spin. Most visitors want to be close to the downtown core near the Charleston City Market and restaurants. We chose The Ryder Hotel on 237 Meeting Street because it’s a new boutique hotel within walking distance of the downtown area. The Little Palm bar at The Ryder is a great place for a glass of champagne, beer, or mixed drinks.

Near the center of downtown, French Quarter Inn is right next to the Charleston City Market, offering upscale lodging a biscuit’s throw from most attractions, shopping, and restaurants in or near the market.

Wentworth Mansion is another high-end hotel and features Circa 1886 restaurant on-site, a tasty plus! Several chain-type hotels offer budget lodgings such as Homewood Suites, Springhill Suites, La Quinta Inn and Suites, and others.