5 Days in Charleston

Being from Charleston, SC, I am always eager to share my list of recommendations with any stranger who is traveling to the Holy City and willing to listen. From the historic homes with piazzas to its charming cobblestone streets and heavy heavy Southern cuisine, it’s no wonder that Charleston has been recognized by Conde Nast Traveler as the #1 city in the US for the past gazillion years.

When I travel back to Charleston, we are typically going to a friend’s wedding or to visit my mom. What makes this itinerary unique is that it’s my ideal itinerary if I were going to Charleston for a vacation. It’s a compilation of 20+ years of living in the Charleston area and 10+ years of traveling there… it’s a mix of classic Charleston and new Charleston. Until now, I’ve been sending this list via text or email to friends - making edits each time as the city changes and evolves.  

It was extremely hard to develop this itinerary. I kept coming back to it for over two months. My typical post means sharing exactly what we did - a recap of our itinerary. In this case, I had to take my knowledge of hundreds of places in Charleston and distill it down to the best of Charleston which proved itself to be challenging. Everyone has hard and fast opinions about the best of Charleston so feel free to leave a comment with your favorites. 

5-DAY ITINERARY IN CHARLESTON

DAY 1: Arrive in Charleston. Head to lunch at Cru Cafe. Then, opt for a historic tour of Charleston and a little shopping on King Street. Before sunset, walk along the Battery and Rainbow Row before grabbing sunset drinks at Vendue Inn Rooftop. Enjoy dinner at Edmund’s Oast or Obstinate Daughter on Sullivan’s Island.

DAY 2: Meander to brunch at 82 Queen, then head to the beach or continue shopping along King Street and stroll through the College of Charleston’s Campus. Dinner at The Darling Oyster Bar, and end your night with a night-cap at Camellias Champagne Bar.

DAY 3: Grab breakfast at Callie’s Hot Little Biscuit, head to Kiawah Island Resort for the next two nights. Relax on the beach. Enjoy dinner at Jasmine’s Porch and a night-cap at The Lobby Bar. 

DAY 4: After room service, rent bikes to ride along the nature paths, go kayaking, and then relax at the spa. Opt for dinner at The Ocean Room.

DAY 5: Visit the Angel Oak Tree. Stop by Rodney Scott’s BBQ before heading home.

If you choose not to stay at Kiawah Resort and want to stay in Charleston longer, I have more Charleston restaurant recommendations below to extend your visit.

Where to stay: 

Kiawah Island Resort - We always receive the best-service at Kiawah. When our dog was scared to take the stairs in our villa, the team wrote a hand-written letter of encouragement to Chuck, accompanied by treats. If you’re traveling with a family, a villa is the way to go. If you’re looking for the full-resort experience, book an Ocean View room.

Belmond Charleston Place - A classic Charleston hotel, this hotel on Lower King Street is in the perfect spot for exploring and one of our new favorites after recently staying there for a wedding.

Hotel Bennett - While I have not personally stayed here, we were married at its sister hotel in Middleburg, Virginia so I can vouch for the service and level of astuteness. From my recent visit to Camellia’s Champagne Bar inside the hotel and hearing from friends who have stayed, I can already tell you that the hotel is worth booking.

Airbnb - I would recommend staying in downtown Charleston if you are researching an Airbnb. For walkability, I would recommend looking anywhere south of Spring Street. To receive $55 off your first trip, you can book Airbnb with my link.

Fried green tomatoes at Cru Cafe

Where to eat: 

Edmund’s Oast - Named after a historic rebel brewer in Charleston, this restaurant continues to be on my visit list. I can’t go without ordering at least one PB&J beer (and you shouldn’t either).

82 Queen - A Charleston classic known for it’s southern fare, I always opt for an outdoor table and the fried chicken & waffles (which is perfect for nursing yourself back to health if you enjoyed a few drinks the night before). 

Cru Cafe - Don’t miss this super cute gem of a restaurant near Market Street. You’ll be charmed by its location in a historic house; I suggest getting a table on the porch and ordering the fried green tomatoes. 

The Darling Oyster Bar - You’ll find Darling Oyster Bar in a 19th-century storefront on Upper King Street. It’s the perfect place to prop up at the oyster bar, order a cocktail and enjoy fresh seafood.

Rodney Scott’s BBQ

Callie’s Hot Little Biscuit - There’s a reason there’s a line out the door which is why you should get up earlier to beat the crowd and experience the amazingness of these biscuits! 

Obstinate Daughter - This Southern restaurant on Sullivan’s island is influenced by Italian, French and Spanish cuisine; I definitely recommend ordering any of the pasta dishes or pizza. They have a fun Southern spin to their entire menu.

Camellias Champagne Bar

Rodney Scott’s BBQ - Don’t you dare leave the Lowcountry without having BBQ, specifically Rodney Scott’s BBQ. Originally a BBQ restaurant from upstate South Carolina, Rodney Scott’s BBQ is a counter-service restaurant on Upper King Street but don’t be fooled - it fills up fast so go early. Fun fact: Chef Rodney Scott has been nominated for a James Beard Award for Best Chef of the Southeast.

Goat Sheep Cow - Obsessed with this spot after a recent trip to Charleston, there are two locations. The Church Street shop is the most adorable place to grab wine and cheese for an afternoon snack to go; if I could pack up the store and take it home with me, I would, and I’d be in trouble. Their Meeting Street location is where you’ll go for a romantic seat at the bar.

OAK Steakhouse - I seriously adore the setting from its arched windows, very historic hardwood floors, and exposed brick walls, the ambiance is a perfect pairing for steak and a bottle of wine.

Gaulart & Maliclet/Fast & French - This restaurant introduced me to communal dining back in 2007. Get ready to cozy up next to fellow patrons. I highly recommend any Open Faced sandwich on their menu. It’s no wonder this spot has remained a mainstay on Broad Street for over 30 years.

Where to grab a drink: 

Belmont - Upper King Street

Blind Tiger Pub & Courtyard - Broad Street

Camellias Champagne Bar - Upper King Street

Citrus Club - Upper Meeting Street

Cocktail Club - Upper King Street

Vendue Inn’s Rooftop - South of Broad Street

Vintage Lounge - Upper King Street

Common Questions

Folly Beach or Isle of Palms? Either. Isle of Palms is refined and commercialized with paid parking, restaurants along the beach and showers to wash off after; Folly Beach is less refined (no showers, street parking, etc.). If you do make it to Folly Beach, I highly recommend Taco Boy and order a frozen screwdriver to cool off. 

When should you go? July and August are smoldering with high levels of humidity and an afternoon thunderstorm. The weather is really nice in April, May, September and October. There are great events throughout the year like Charleston Food + Wine Festival and Spoleto Festival USA but if you don’t plan to attend those then I would steer clear of those weekends as the streets can be overcrowded; the same applies to graduation weekends too.

Do you need a rental car? If you plan to only stay downtown, a car is unnecessary. I recently traveled to Charleston with a group of 9 for a friend’s Bachelorette. We stayed at an airbnb on Isle of Palms and were able to travel in Lyft or Uber the entire time without any trouble. However, if you think you’ll be doing a lot of exploring to the outskirts of Charleston like Kiawah Island, and need the freedom and independence that comes with a rental car, then I would recommend one.