My Guide to Charleston: a perfect weekend

don't go to the Pineapple Fountain

On my second date with my husband Jon, he told me his dream was to live in Charleston, South Carolina. In my mind, Charleston meant eating biscuits and gravy on a blazing hot afternoon in a Lily Pulitzer dress. I just couldn’t imagine myself there.

Five years later, I’m writing this from my kitchen counter in my home here. You’d have to drag me out of Charleston. It’s a city full of art and food and European influence. It’s a place you can be outdoors all year round. But if you didn’t know your way around the city, you could end up re-creating the southern fever dream I used to picture. If you’re visiting Charleston, *do not* plan your trip around the pineapple fountain, the Charleston City Market, or a carriage tour. Do not stand in line at Hyman’s seafood. LET ME HELP YOU.

Thare so many different ways to experience the city, so this is just one of many guides to come. But to start, we’ll create A Perfect Weekend.

FRIDAY

3:00 - Check into your hotel.

I haven’t stayed overnight in any of these hotels, but love to hang out in their restaurants or coffee shops. If we were going to book a staycation, we’d choose one of these: (note: the prices can really vary based on season & day of the week. Depending on when you come, these could be $150-200 a night, but if you’re catching them in the high season on a popular weekend, the prices can skyrocket).

• Ryder Hotel

• Hotel Emeline

• Post House Inn - located off the peninsula in Mount Pleasant’s Old Village, if you’re looking for a quieter location away from downtown. Even if you don’t stay here, you should try a burger (or butterbean burger, my fave!) at their restaurant.

5:00 - Apertivo Hour at Babas on Cannon

• You’ll start your evening at Babas on Cannon: my favorite coffee shop that turns into my favorite bar at 4pm. It has a community-centered European vibe, and if you walk past on any given evening, you’ll find people sipping Aperol spritzes from cafe tables on the street. On Fridays & Saturdays from 4-6, they do this thing called Apertivo Hour where they put out an insane spread of food (homemade foccocia bread, olives, sardines, artichokes, dips, etc) that you can eat FOR FREE if you just buy a drink. It’s the favorite weekend ritual of everyone I know.

  

  

6:00 - Dinner at Malagon

Next, let’s head to Spain, aka Malagon, for tapas. It’s only a 4 minute walk from Babas, and they have lots of delicious small plates and great wine.

If you’re in your 30’s like me, after dinner you’ll want to wind down at your hotel (watch a show in bed). But if you’re looking for dessert or a nightcap, these are great places:

• Carmella’s for dessert & walk around waterfront park

• The Griffon, a historic pub absolutely covered in dollar bills from floor to ceiling. You can play some darts and staple your own autographed dollar bill to the wall.

• The Watch or The Vendue for a rooftop

• Felix Cocktails et Cuisine, if you want somewhere on King Street that isn’t in the middle of all the craziness (it can get rowdy on King Street at night).

SATURDAY

Good morning, it’s day 2! You’ll probably want to start your day with brunch. Brunch in Charleston is like an Olympic sport. You can stand in lines for 1-2 hours, and by the time you’re seated with your food, was it even worth it? I prefer a quick breakfast to standing in line. Here are my two favorites:

• The Daily - order at the counter for quick, light & fresh food. I always get the breakfast pita. So good.

  

• Little Line - another order-at-the-counter situation with patio seating. Great coffee, service & food.

If you don’t mind waiting and want the full, sit-down brunch experience, I’d do Miller’s All Day (downtown location).

11:00 - Walk King Street, South of Broad neighborhoods, & see the Battery

If this is your first time to Charleston, you’ve got to see a few of the obligatory sights: Rainbow Row, the Battery, & White Point Gardens. But they’re not the main events. The ~journey~ is the main event.

• Start on King Street with a quick coffee from Mudhouse (and check out their back garden!), and walk towards the battery.

• Optional: stop at Target on King Street for an Olipop to sip while you walk, or at Off Track for the literal best ice cream you will ever eat (idk what time it is, but you’re on vacation it’s fine).

• Once you pass Oyster Point Real Estate (still on King), start wandering. Go down whatever street you think looks cool — there are so many beautiful streets, houses, and hidden alleys. My favorite activity is still exploring and pointing out our favorite things about these houses. You always notice something different.

• Eventually end at The Battery, stroll White Point Garden, and see the colorful houses at Rainbow Row.

1:00 - Walk to Harken Cafe for late lunch

Next you’ll head to Harken, an 8-minute walk from Rainbow Row. Harken is a favorite. They can do no wrong. The shop is beautifully designed, full of antiques slowly curated over years by the owner. They have delicious baked goods and food. Grab a sandwich, a slice of quiche, or try one of their daily salads.

2:00 - Head back to your hotel

Walk or drive back to wherever you’re staying. Rest up, because you’re getting in line for dinner at 4!

4:00/4:30 - Stand in line at Chubby Fish

Okay, I know I said I hate lines, but I WILL line up for Chubby Fish. Chubby Fish is my favorite restaurant. They don’t take reservations, but it’s so good that people stand in line every day at 4:00 (the restaurant opens at 5) just to put their names in for a slot for dinner. The line usually goes all the way down the block, but the vibes are high. Bring a friend or a book. It’s worth it, I promise.

5:00 - Grab a glass of wine at Elliotboro Mini Bar

Once you’ve made it to the front of the Chubby Fish line and chosen your dinner time, walk to Elliotboro Mini Bar (Google maps says it will take 1 minute). It’s the tiniest cutest neighborhood bar, and they usually have some form of open mic/live music going on.

7:00 - Chubby Fish

Enjoy your dinner — it’s going to be GOOD. The menu changes seasonally, but they keep some of their staples all year round. We can usually get the celery salad and the tuna belly toast (or crudo) every time.

SUNDAY

Hopefully you leave on Monday, because we haven’t even made it to the beach yet! Here’s your last day in Charleston.

9:00 - Coffee at Sightsee & take a quick stroll in Hampton Park

I spend a lot of time in Hampton Park —it’s where my friends and I walk, run, and hang. So when we found out Sightsee Coffee was opening a shop at the corner of the park, it was the best news. Grab a coffee or a matcha and walk through the park.

The designer of Central Park in NYC also designed Hampton Park

11:00 - Drive to Sullivan’s Island

There are three main beaches in Charleston: Folly, Sullivan’s, and Isle of Palms. My favorite is Sullivan’s for so many reasons. Find a parking space (good luck) and explore the little beach town.

• Visit Maker’s Post for a pretty souvenir

• Grab a bite to eat at Poe’s Tavern, Sullivan’s Fish Camp, or if you’re lucky, Obstinate Daughter (it’s hard to get in)

• Or, get a sandwich from Co-Op and take it to the beach!

• Depending on the time of year, go for a swim, read in the sun, or take a beach walk (even if it’s cold out! I <3 winter beach).

2:00 - Stop at Shem Creek on your way back

If you’re driving back to downtown, you’ll pass Shem Creek on your way. It’s a little collection of bars & restaurants on the water. Grab a beer or a lemonade and watch boats, kayakers, and dolphins in the creek.

4:00 - Rest at your hotel

zzz

6:00 - Happy Hour at Coterie

This is our favorite spot for happy hour, which goes from 5-7pm. $8 cocktails & wine, and light bites as cheap as $6.

7:30 - Stella’s for dinner

An 1-minute walk from Coterie is this cozy Greek spot with amazing food. They’re known for their pastas, but every single thing I’ve tried is delicious.

9:00 - Goodnight

Thanks for coming along on a Charleston weekend—there are so many more spots to share, so stay tuned for more city guides.