Looking for an out-of-state holiday road trip in a city full of charm that makes it feel like it’s straight out of a storybook? Charleston is the place to go. Imagine strolling picturesque historic streets lit with twinkling lights, sipping a seasonal cocktail at a pop-up bar and stopping at festive markets around every corner. Here at the DiG, we love to give you all the insider tips to make the most of your experience and for Charleston, we suggest you kick off planning your adventure by signing up for Explore Charleston’s Advent Calendar on their website. Starting on December 1, Explore Charleston will send holiday recipes, local gift ideas and unique traditions straight to your inbox.
The holidays in Charleston are full of family-friendly fun, but for us adults (yes, we’re still kids at heart!), there’s something extra magical about a holiday pop-up bar. And trust us, Charleston’s festive sips are not to be missed. From cozy speakeasies transformed into winter wonderlands to rooftop lounges decked out in garlands and lights, there’s a pour for every palette. Most of Charleston’s holiday pop-up bars open in early to mid-November and go until the first week of January. Check out popular holiday pop-up bars like Little Pine at Little Palm, Bar Mash’s annual Bar Mashmas, Blind Tiger, Sippin’ Santa and more. Did someone say Gingerbread House Espresso Martini? Say no more because our bags are already packed.
Charleston’s charm doesn’t stop with its holiday pop-up bars and festive cocktails, and no festive visit would be complete without checking out the Festival of Lights at James Island County Park. Families and visitors of all ages can make lasting memories by cruising along a three-mile display and enjoying over two million lights. There are also events like The Charleston Santa at the Best Friend Train Museum, offering commemorative photos while supporting Toys for Tots.
Beyond the events, it’s Charleston’s historic streets, waterfront parks and shopfronts adorned with garlands, bows and twinkling lights that truly capture the spirit of the season. Why rush back home when Charleston offers the perfect setting for a cozy weekend escape? Many of the city’s boutique hotels and historic inns roll out festive holiday packages that pair luxurious stays with curated experiences. For instance, The Spectator Hotel, located in the heart of the Historic District, presents the Holiday Cheers with Spectator Spirit package. When you book the Sleigh Bell Suite at the French Quarter Inn, a $100 donation will be made by the hotel to St. Jude’s Children’s Research Hospital. Some hotel deals also include tickets to the Holiday Festival of Lights. For a full list of holiday hotel offers for your trip to Charleston, check out Explore Charleston’s website. Whether you’re planning a family getaway, a romantic escape or a solo holiday adventure, Charleston delivers the perfect combination of history, charm and festive magic.