Pack your bags! We’re certain you’ll be ready to book a trip to Charleston after exploring this expert travel guide. We teamed up with the oh-so-charming Charleston local Jillian Attaway of the fashion, travel and lifestyle blog Rhyme & Reason to reveal the best of the best in three of the most important categories: checking in, dining out and exploring around. Scroll on to explore Jillian’s top picks!
Don’t forget to check out our curated travel itineraries before you go!
Charleston in and of itself is a city filled with romance and charm. When checking in with your special someone, look no further than boutique hotel 86 Cannon. Named for its address on Cannon Street, 86 Cannon oozes romance through the walls of the mid 18th century fully restored old home.
Every room has a cozy feel that will make you never want to step outside until you see the clock strike five o’clock for the nightly wine and cheese spread on the sweeping piazza. Be prepared to fall in love and turn this romantic retreat into a yearly occurrence at 86 Cannon!
Charleston’s reputation as a foodie capital in America definitely precedes itself, which is why it’s no surprise that people travel from all over to taste the delicious food of the Lowcountry. While in town, you’ll no doubt want to try all the local Southern food, seafood and everything in-between, but I suggest starting your food journey right upon check in by staying at Zero George.
The property consists of 16 guest rooms, a courtyard, a grand piazza, a living room, an intimate bar and one of the most delicious restaurants in town, Zero Restaurant + Bar. The chef serves up new American cuisine and also hosts cooking classes that are equally as fun as they are delicious. There isn’t a tastier or more authentically Charleston hotel in the city than Zero George so be sure to arrive hungry and be prepared to never want to check out of this historic spot.
The Dewberry is the perfect hotel to check into with all your best girlfriends in tow. The hotel boasts a very old world meets modern vibe that shines through in each and every guest room and really comes to life at the buzzing bar. You’ll want to start every evening gushing over the day’s fun with the girls on the plush couches in the bar while live music fills the room and delicious specialty cocktails are served.
The Dewberry is also THE girlfriend getaway spot because every room comes with cozy terry bathrobes and slippers, it is designed to the nines with mid-century modern décor, including to die for wallpaper, and has a second bar on the roof set to open this spring.
Sundays in the South are one of my favorite days of the week because I simply love a bubbly Sunday brunch! My top recommendation for brunch is also one of my favorite dinner restaurants, the colorful and lush Cannon Green.
The bright, airy space is beautiful and is made even more special by the large custom paintings on the walls by local artists Teil Duncan, Lulie Wallace and Blakely Little. The creative cuisine at Cannon Green is always local and seasonal while the lovely libations will have your taste buds doing a happy dance. There is also a DJ at brunch that sets the tone of a lively brunch experience and the perfect start to your Southern Sunday.
After a day exploring Charleston, do as the locals do and unwind with a glass of wine and a charcuterie board at Goat Sheep Cow North. I’m biased to all things Charleston, but I think Goat Sheep Cow North is the best wine bar & shop I’ve ever been to!
The wine selections will exceed your expectations while the charcuterie boards are a work of art that are almost too beautiful to eat. The atmosphere at Goat Sheep Cow North is so warm and welcoming that you’ll have a hard time deciding where you want to sit and relax… the deep comfy booths, the inviting bar space, or the lovely patio.
Leon’s is where I always send friends and family who are looking for Southern food while visiting Charleston. Leon’s is so standout because the food is inventive and can best be described as Southern food with a twist. You’ll find everything from fried chicken to hush puppies to oysters to avocado toast to an Asian chicken salad.
For dessert, Leon’s does old fashioned right with soft serve ice cream. The restaurant resides in an old body shop so it gives off a laidback yet cool vibe. Don’t miss the spacious patio on a sunny day or a warm night. Leon’s is a favorite among locals and visitors alike!
Charleston has a wonderful shopping scene. There are so many creatives in the city so it has a wealth of different types of shops. Two of my must-visit shopping destinations are Hampden Clothing and Croghan’s Jewel Box. Hampden's owner, Stacey, buys the most beautiful clothing, shoes and accessories and is always introducing me to new lines and designers. At over 100 years old, Croghan’s Jewel Box is Charleston’s oldest family owned jewelry store. You’ll find beautiful estate and antique treasures as well as modern pieces and Charleston’s own Goldbug Collection.
Mac & Murphy carries the most adorable stationary, cards, gifts and more. Another favorite, Candlefish, is your one stop shop for all things candles (they even have candle making classes too!).
Charleston has beautiful weather year-round, so spending time doing an outdoor activity is more than ideal! My absolutely perfect Charleston evening consists of a sunset walk with my puppy or a bike ride in the South of Broad neighborhood where you’ll find colorful Rainbow Row and live oak tree lined White Point Garden nestled right on the water.
The best way to get the lay of the land in Charleston and to learn about the city’s rich history is to spend an hour outside on a carriage ride with Palmetto Carriage Works. The Charleston area also boasts a handful of historical and sprawling old plantations. The must-see plantations to visit for history tours and garden wanderings are Boone Hall Plantation, Magnolia Plantation and Middleton Place.
Charleston has a lot to offer in terms of indoor activities! One of my favorite ways to spend a leisurely afternoon is wandering around The Gibbes Museum of Art, admiring the exhibitions and the architecture of the building itself. It is one of the best museums in the South!
Nights in Charleston are full of music, theater and culture. I can’t recommend spending an evening at Charleston Music Hall to see the Charleston Jazz Orchestra enough! If theater is your cup of tea, then check the schedules at my two favorite theaters, Pure Theater and Woolfe Street Playhouse… my husband and I always enjoy ourselves. When booking a trip, keep in mind that Charleston celebrates music, art and theater like no other during the annual Spoleto Festival in May and June.