It was Memorial Day weekend and it was time to celebrate the start of summer with a long weekend trip to Charleston, SC with friends. Ray and I have been to Nashville, but the American South is still pretty uncharted territory for us, so we were excited to check a new Southern city off our bucket list.

When we went: We spent 4 nights and 5 days in Charleston over Memorial Day Weekend, which is probably one of the busiest times of year to visit, but it was a perfect long weekend all the same. We got pretty hot weather (high 80s and humid) our first day, but somewhat overcast and more mild the rest of the time.

Use the table of contents below to jump around and plan your own perfect Charleston weekend getaway!

GETTING TO & AROUND CHARLESTON

We flew from Denver directly to Charleston which is about a 3.5 hour flight. For the first 3 days we relied on Uber and Lyft to get around, but sometimes we faced long waits since cars were tough to come by during the crowded weekend. For the last couple days, we ended up renting a car so we could venture beyond the historic downtown part of the city and see some new sights. If you’re going to be in Charleston more than a couple days, a car rental is definitely worth your while for part of your trip.

CHARLESTON BUDGET BREAKDOWN

We weren’t really on a budget for our Charleston weekend — it was a friend’s 30th birthday and we hit some nice places, but also didn’t break the bank. Here’s how our expenses broke down — all prices are per person:

Flight: Round trip Denver >> Charleston on Southwest - $358pp
Airbnb (2 nights - shared by 4 people): $308/night - $154pp
The Ryder Hotel (2 nights - shared by 2 people): $369/night - $369pp
Airbnb Experience — Sailing Trip: $99pp
Airbnb Experience — Historical Walking Tour: $35pp
Visit to Boone Plantation: $23pp
Rideshares: $34pp
Car Rental (2 days): $240 - $60pp
Food / drink: Probably around $100 per person per day if not more, considering we bought a bunch of alcohol for the sailing trip and the Airbnb, and ate and drank for the majority of the trip - $500pp
Total per person (5 days): $1,632
Total per person per day: $326.40

WHERE TO STAY IN CHARLESTON

We stayed in two different places — one Airbnb and one hotel — just to get more experience in during our short stay.

Spot #1: The Inns at 40 Spring Airbnb

Located right at King and Spring, this historic 2-bedroom Airbnb apartment is right in the heart of all the action and made a great base for exploring downtown Charleston. Great spot for two couples to crash. It is a noisier, bustling area, so if you’re looking for a quiet relaxing getaway this may not be your spot — but we just drank plenty every night and then blasted fans for white noise and slept just fine :)

In front of The Inns at 40 Spring Street — I was feeling the stone cold RBF vibe apparently.

Spot #2: The Ryder Hotel

The Ryder Hotel is about 10 blocks south of our Airbnb, and still made a great spot for exploring downtown. We booked the Ryder on its opening weekend, so it was our first time being the very first ones to stay in a hotel room. The Ryder is styled like Palm Springs or LA in the heart of downtown Charleston, and everything is incredibly ~aesthetic~. It features a tiny pool that’s more for lounging around with a pretty cocktail in hand than for swimming in (it actually wasn’t even ready to swim in yet when we were there). You could say it’s a vibe. Being opening weekend, everything wasn’t perfectly ironed out in terms of the hotel operations, but we still thought it was super cute and enjoyed our time there.

WHERE TO EAT & DRINK IN CHARLESTON

Our favorite part to write about, because we definitely plan our trips around food. We ate and drank — a lot! — during our weekend trip to Charleston. Here’s everywhere we went — most delicious, and one hilariously bad!

Downtown Charleston

The Darling Oyster Bar

513 King St, Charleston, SC 29403 | Website

This was our first stop as soon as we landed in Charleston and checked into our Airbnb. Local seafood is the star of the show at The Darling, located right off bustling King St. in a beautifully restored 115-year-old storefront. We grabbed ourselves some oysters, crab dip, and white wine to kick the party off right and launched right into a weekend of exploring, wining and dining.

Proof

437 King St, Charleston, SC 29403 | Website

After oysters and feelin’ great, we only made it about a block further down King before we decided to tuck into another beer and cocktail bar. We sat and the bar and got some delicious craft cocktails. I wish I remembered the name of our drinks because they were all good, but all I can remember is to go with the gin. Our friend Drew kept picking the tastiest drinks all weekend by following this strategy and I highly recommend the tasty gin drinks at Proof.

Indaco

526 King St, Charleston, SC 29403 | Website

We didn’t have dinner reservations on our first night of the trip, so the key was just to drink for hours and then wander into this lovely Italian restaurant super late after most parties had finished their meals. Yes, we were pretty drunk and hungry, but we have a feeling this food would have been delicious anyway. We shared a couple pizzas, a couple pastas, and a bottle of wine and everything was superb.

Warehouse

45 1/2 Spring St, Charleston, SC 29403 | Website

After Italian food it was right back to the drinks. Warehouse was right across the street from our Airbnb so we couldn’t resist a little nightcap to close out our first day. Charleston is a college town, and Warehouse made that exceedingly apparent. The DJ was great, but as this was our friend’s 30th birthday trip, the crowd made us feel awfully old. We leaned all the way into it and showcased our best awkward dance moves front and center.

Brown’s Court Bakery

199 St Philip St, Charleston, SC 29403 | Website

Located in a historic bi-level building right around the corner from our Airbnb, Brown’s Court serves a large selection of fresh-baked bread, pastries, confections and breakfast items daily. But get there early for breakfast! We thought we were pretty early around 9-9:30am, but a lot of the breakfast items were already sold out. We got some donuts, coffee, and ham & cheese croissants that were all amazing though.

Carmella’s

198 E Bay St #100, Charleston, SC 29401 | Website

Carmella’s is a cafe known for its desserts but also offering a variety of coffee, sandwiches, wine, beer, and cocktails. We stopped at Carmella’s for some quick sandwiches and a coffee pick-me-up before our sailing adventure, but we also walked by it late at night and saw that it had turned into a raging bar. What a versatile little queen!

The Rooftop Bar at The Vendue

19 Vendue Range, Charleston, SC 29401 | Website

After failing to get up to the rooftop bar at The Dewberry hotel near our Airbnb (turns out it closed really early the night we went?), we tried our luck at The Vendue and got to enjoy some refreshing rooftop spritzes with a view of both the water and the city.

Bin 152

152 King St, Charleston, SC 29401 | Website

We made dinner reservations at Husk almost two months in advance, and even then the only time we could lock down was 9:45pm, so after trying to show up early and failing, we hit up Bin 152 a couple blocks away and loved it! Delicious wine, charcuterie, and cheese pairings. We had to stop ourselves so we wouldn’t get too full for Husk but could have made a whole dinner out of that bread and cheese.

Husk

76 Queen St, Charleston, SC 29401 | Website

And that brings us to Husk, the Charleston dining experience we’d been waiting for. Husk’s seasonal menu showcases local Lowcountry ingredients and cuisine, and it’s a truly special dining experience. We shared a bunch of appetizers and I got the Cornmeal Fried NC Catfish as my entree which I’m drooling thinking about now as I get hungry for a bedtime snack. Our biggest Husk tip of all...don’t sleep on the “Dragoon’s Punch.” According to the menu it’s a recipe from 1792 featuring California brandy, Barbados rum, peach brandy, black tea, lemon juice, and raw sugar and boy does it go down easy. We’ve yet to try recreating this punch at home but it’s on our to-do list because we think it just might be our favorite new drink.

Burns Alley Tavern

354B King St, Charleston, SC 29401 | Website

Sure, we love a good cocktail, but a classic dive bar is where we feel most at home — and that’s just what we found in Burns Alley. We ended up here on two different occasions, both much later in the evening, and the second time we found ourselves graced with a live band that absolutely slapped. Glad we ventured down the alley to find this dive.

Blind Tiger Pub

36-38 Broad St, Charleston, SC 29403 | Website

Another historic venue. Another colleg-y bar. With very rude bartenders. We actually saw a rat there. And according to the website it’s also haunted. So...try at your own risk?

Don’t Recommend: Hyman’s Seafood

215 Meeting St, Charleston, SC 29401

And last, *definitely* least for the downtown area, Hyman’s. There we were, exploring and getting hungry for lunch, but everywhere was packed due to Memorial Day. We looked up seafood places near us and Hyman’s popped up with tons of reviews. The second we got there we knew we’d made a mistake. It was definitely your standard tourist trap — celeb photos all over the walls, cheesy quotes on the tables, giant menu, gift shop. But we were too far in — we were hungry, indecisive, and knew we didn’t have good chances of getting in somewhere else — so we went for it. Our favorite (least favorite) parts:

The old man named Byron standing out front handing out hush puppies. He told us a very awkward story about how he once drank too many Hyman’s margaritas, and he singled out one friend in the group and told her specifically she’d love Charleston.
The owner, Hyman himself, came by and encouraged guests to read the little notecards on every table...which were cringey quips like “the ten commandments of marriage.”
The food...was not great. We later learned that while most of the Charleston food scene offers delicious local seafood, Hyman’s ships in theirs frozen on the daily. Explains a lot.

So while we would not recommend Hyman’s, we somehow continued making up hilarious stories about it and died laughing for the rest of the trip, so overall we’re glad we went.

East Central Charleston

Butcher & Bee

1085 Morrison Dr, Charleston, SC 29403 | Website

A restaurant with a gorgeous outdoor patio that emphasises local and sustainable dishes. Based on the name, tbh we kind of thought this was a barbecue restaurant, so we were surprised to find a lot of fresh, more Mediterranean cuisine on the menu. We got some roasted chicken, kebabs, fish, and my personal favorite drink — Iced Israeli Sachlav (cold brew, oat milk, rose water, cinnamon, coconut, and spiked with rum!)

The Tattooed Moose

1137 Morrison Dr, Charleston, SC 29403 | Website

Had to find a friendly dive bar for post-dinner drinks after Butcher & Bee, and The Tattooed Moose was just a couple blocks up the street. We grabbed some beers but saw “duck fat fries” on the menu and couldn’t resist a post-dinner snack too.

Revelry Brewing Co

10 Conroy St, Charleston, SC 29403 | Website

Craft beer, a rooftop, and good vibes. This area of Charleston is a bit industrial at the moment and we can just see it booming in the next couple years. For now, Revelry stands somewhat alone among office buildings and neighborhoods, and while still very popular, the setting is a welcome escape from the bustle of downtown.

Lewis Barbecue

464 N Nassau St, Charleston, SC 29403 | Website

We went to Lewis at a pretty random time of day — I think around 2pm or so — and there was still a long line, so I can only imagine how busy it gets at your standard lunch or dinner hours. To our surprise though, they also have a Mexican food stand out front that sells margaritas you can sip while waiting in line for your BBQ feast, and the line actually went super quickly. This meal, though! We ordered way too much because we wanted to try everything. I know barbecue is all about the meat, but I’m a sucker for the sides and these did not disappoint. We tried so many things: brisket, “hot guts” (sausage), collard greens, mac & cheese, pinto beans and do not sleep on the green chile corn pudding! We definitely needed a nap after this stop.

Edmund’s Oast

1081 Morrison Dr, Charleston, SC 29403 | Website

Edmund’s Oast is right next door to Butcher & Bee, and the night we went to B&B there was actually a wedding at Edmunds in their gorgeous outdoor patio. We had some time before heading to the airport on our final day and decided to go back! We had some great beer and cocktails, but the food looked amazing as well so it would definitely make another great dinner spot in the East Central area.

Sullivan’s Island

We spent a brief couple hours on Sullivan’s Island grabbing lunch at Poe’s Tavern and bloody marys at Dunleavy’s Pub, then exploring the beach. Poe’s is a bustling spot with a huge amount of outdoor seating and solid food, and Dunleavy is a perfect Irish pub where we were the only customers at that time of day. If we had been able to, we would have gone to Obstinate Daughter for lunch, but the hostess told us there was a 5 hour wait with a totally straight face, and we just turned around and booked it to the trusty Poe’s.

Folly Beach

On our last day in South Carolina we went on down to Folly Beach and hit up Lost Dog Cafe for breakfast. Think breakfast all day, fresh-baked muffins and cinnamon rolls, giant burritos, bagel sandwiches, grits, and more. It’s a crowded spot, especially if you get sat inside like we did, but it’s a perfect beachy breakfast destination.

WHAT TO DO IN CHARLESTON

Now you understand that our primary activities in Charleston were eating and drinking. But even with a heavy dining itinerary, we managed to fit in a few other experiences that helped us get a taste for Charleston’s history, culture, and natural landscape. Here’s what we did:

Charleston Boat Tour

We took at 2.5-hour sailing trip around Charleston Harbor on the sailboat Mental Heeling, hosted by Captain Jay and crew and available on Airbnb Experiences. Only one other couple was on the boat with us, and we had a great time drinking, lounging, chatting up Jay and his first mate, and seeing the harbor.

This Airbnb Experience description mentions the opportunity to help man the sails…which we did not do at all.

Historical walking tour or haunted walking tour

From the colonial era to now, Charleston has a fascinating and devastating history marked by war, the slave trade, natural disasters, disease, and more. We did this 2.5-hour walking tour, and man, that’s a long time to walk around in the heat and listen to history (for me, anyway). But that said, we learned a lot, saw some beautiful architecture, and stood on the sites where some of Charleston’s biggest historical events went down.

Haunted walking tours are also a big thing in Charleston and they take place at night for more of a spooky vibe — I have a feeling these tours might be more up my alley next time I go back!

Charleston walking tour — highly recommend sneakers as Kait is wearing and not platform sandals which were a poor choice on my part.

Boone Hall Plantation

Boone Hall is a historic plantation in Mt. Pleasant about 25 minutes from downtown Charleston. The plantation used enslaved labor until the Civil War, and is one of America’s oldest plantations still in operation. Boone Hall is open for tours, where you can walk the grounds and see the Colonial-revival style dwelling (notably Allie’s family’s summer home in The Notebook), the slave cabins, and the iconic southern live oak trees draped with Spanish moss.

Beach it up

We hit the beach both on Sullivan’s Island and Folly Beach. Sullivan’s Island Beach is located along a more residential stretch, and it was kind of a rainy day when we visited so we just stopped by. Folly Beach is described as having a “bohemian” vibe by the locals...but for us people from the west coast, there’s really nothing bohemian about the town or beach at all. Maybe a more relaxed, just beachy vibe? This is a super long and pretty crowded stretch of beach great for lounging — but keep in mind we went over Memorial Day so everything was more packed than usual. If you’re in Charleston for more than a couple days, we definitely recommend renting a car for a day and hitting the beaches and/or historical sites outside the city.

Exploring the beach on Sullivan’s Island

What to pack for a Charleston weekend getaway: You won’t need anything special for your Charleston weekend, just whatever cute outfits you want to wear for you many dining, drinking, beaching, and exploring adventures. Here are a couple items you can see me wearing in the photos above, or ones on my list for my next trip.

Just bought these vintage cat-eye sunnies for myself
I love my platform sandals, but please don’t do what I did and wear them on a 2.5-hour walking tour 🙃
I was all about gingham during this trip. This gingham sundress, gingham puff-sleeve dress, and gingham midi skirt would be super cute for your Charleston trip!
Beach hat and travel size ocean-safe sunscreen — protect that face and skin while you’re having fun in the sun!

Hope you found this guide helpful when planning your own perfect weekend trip to Charleston, SC. Questions? Charleston experiences of your own? Comment here or on our latest IG post.

Happy travels!

Hey there!

Jul 11 Guide to a Perfect Charleston Weekend Getaway

TABLE OF CONTENTS

GETTING TO & AROUND CHARLESTON

CHARLESTON BUDGET BREAKDOWN

WHERE TO STAY IN CHARLESTON