Two weeks ago, I had the privilege of working with Explore Charleston on their blog and their Instagram. I took over their Instagram for a day by sharing two photos (one, two) and by taking their followers along with me for my perfect Charleston day! I’m recapping that day today on my Instagram (follow along!) and am excited to share more from the blog post I wrote for the Explore Charleston site today on Rhyme & Reason! Pack your bags because you’ll be ready to book a trip after you read this travel guide! The Holy City has so much to offer that it can be hard to know where to start. So I’m here to make your life easier by bringing you the best of the best! In my Beginner’s Guide to Charleston, we’re focusing on the three most important categories: checking in, dining out, and exploring around! Enjoy!
P.S. I have a lot more Charleston recommendations in my full Charleston Travel Guide!
Top Pick for a Girlfriend Getaway: The Dewberry
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. It shines through in each and every guest room and really comes to life in 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. Of course 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. There is also a second bar on the roof set to open in spring 2018.
Top Pick for a Romantic Retreat: 86 Cannon
Charleston in and of itself is a city filled with romance and charm. From the history to the architecture to the twinkling gas lanterns dotting the city, it’s hard to deny the alluring atmosphere. So, there’s no better excuse to visit Charleston than for a romantic retreat! 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 porch. Be prepared to fall in love and turn this romantic retreat into a yearly occurrence at 86 Cannon!
Top Pick for a Foodie Stay: Zero George
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 come taste the delicious food of the Low Country. 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 sixteen guestrooms, a courtyard, a grand porch, a living room, an intimate bar, and one of the most delicious restaurants in town, Zero Restaurant. The chef serves up new American food. Plus, they also host 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.
Top Pick for Brunch: Cannon Green
Sundays in the South are one of my favorite days of the week. 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. It 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 food 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 you southern Sunday.
Top Pick for Happy Hour: Goat Sheep Cow North
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. 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.
Top Pick for an All-Around Restaurant: Leon’s Fine Poultry & Oyster Shop
Leon’s Fine Poultry & Oyster Shop 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 fashion 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. So don’t be deterred if there is a bit of a wait!
Top Picks for Shopping: Hampden Clothing, Mac & Murphy, Candlefish, Croghan’s Jewel Box
Charleston has a wonderful shopping scene. There are so many creatives in the city so it has a wealth of different types of shops. My four must-visit shopping destinations are Hampden Clothing, Mac & Murphy, Candlefish, and Croghan’s Jewel Box. Hampden is the best clothing boutique I’ve ever been to, which is saying a lot! The owner, Stacey, buys the most beautiful clothing, shoes, and accessories and is always introducing me to new lines and designers.
Mac & Murphy carries the most adorable stationery, cards, gifts and more. Candlefish is the one stop shop for all things candles (they have candle making classes too!). 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.
Top Picks for Outdoor Activities: Rainbow Row, White Point Garden, Carriage Ride, Plantation Visit
Most of the year, Charleston has beautiful, sunny weather so spending time doing an outdoor activity is more than ideal! My top picks for outdoor activities around Charleston include taking a walk or a bike ride down Rainbow Row to White Point Garden, picking up a little historical knowledge on a carriage ride, or visiting a plantation.
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. It is Heaven on earth!
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 my favorite company, 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.
Top Picks for Indoor Activities: Gibbes Museum of Art, Charleston Jazz Orchestra at The Charleston Music Hall, Plays at Pure Theater and Woolfe Street Theater
Charleston has a lot to offer in terms of indoor activities as well! 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 seeing the Charleston Jazz Orchestra enough! I love their live shows and am looking forward to their tribute to The Beatles performance this spring. If theater is your cup of tea, then check the schedules at my two favorite theaters, Pure Theater and Woolfe Street Theater… 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.
Thanks so much for reading my Beginner’s Guide to Charleston! I get lots of emails too about specific Charleston recommendations. So please always feel free to reach out with any more questions you have! xx
Photography by Edwin Eversole
I love Charleston so much! Your beginners guide is incredible and really shows the scope of the city. Thanks for sharing!
Thank you so much for your sweet comment!! Made my day! I love Charleston so much too! XO
Great post, Jillian! So excited to return! Can we do drinks at the Dewberry rooftop?!!
Yes, 100% Dewberry rooftop drinks! Can’t wait!! xx