Weekend Guide to Charleston: What to See, Do, and Eat

Whether you’re taking a girls trip, going on a foodie tour, or simply escaping the brutal Northeast winters, Charleston is the place to be. This charming city had me at pastel houses, but the warm temperatures, blooming flowers, and delicious food options convinced me to book a flight.

Charleston is on the smaller side in terms of city size, making it the perfect destination for an extended weekend getaway. From NYC, it’s just a short 2 hour flight away via Jet Blue. We left New York on a Friday morning and came back Monday evening, giving us plenty of time to explore the city and neighboring areas.

With so many beautiful details around every corner, Charleston really is a blogger’s dream. Today I’m sharing my guide to the city, featuring a day by day itinerary of where to visit, eat, and take cute photos for the ‘gram. I hope it inspires you to book a trip! As always, outfit details at the bottom of this post.

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Friday

Take it easy on your first day in the coastal city. Grab a quick bite to eat for lunch at Dave’s Carry Out on King Street. This place is a hidden gem and a local favorite, with some of the best fried seafood I’ve ever had — the scallops are to die for! If you have time, stroll down King Street to get a feel of the city before checking into the hotel.

For first time visitors, it’s generally suggested that you stay close to downtown as it’s very convenient. However, I don’t think it’s absolutely necessary. If you’re looking to save on hotels and don’t mind a slightly further commute, I highly recommend staying in the suburbs. We stayed in a cute little Airbnb in James Island and loved it. It was only a 15 minute drive to downtown and being surrounded by nature (the Airbnb had a private lake!) was so refreshing.

Once you’re all energized from the food and energy of downtown, it’s time to hit the beach! We decided on Folly Beach because of its laid back vibe. Sit back, relax, and soak in the sun.

Enjoy the bustling pier life and grab dinner at Jack of Cups, a trendy and delicious hole-in-the-wall. While their menu changes seasonally, I recommend getting the samosas and cauliflower bruschetta if they have it. Then, head home and get some rest! Saturday is going to be a busy day.

Saturday

Rise and shine! It’s officially the weekend. Grab breakfast/brunch at Callie’s Little Hot Biscuit to start off your day. This place has a line out the door so it’s best to get there early. We got 6 biscuits to share between the two of us, which was plenty.

If you’re craving some dessert, head over to Sugar Bakeshop, known for their yummy cupcakes. Be sure to try the vanilla blueberry cupcake and get a shot outside the adorable storefront!

Now, it’s time to bike! Walking is totally fine too, and absolutely doable. Rent a bike at Affordabike for only $15 for 3 hours. Bike down King Street to begin exploring!

King Street is just one of many with cute houses. Take a slight detour to Second State Coffee on Beaufain Street for the best iced lavender latte you’ll have in your life. There’s also a darling pink house next to it, which is perfect for photos!

Make your way down to the South of Broad neighborhood, which has many of the iconic and historic houses you constantly see popping up on your Instagram feed. Tradd, Church, and Legare Streets were some of our favorites.

Biking in Charleston is very easy (all the roads are flat) and so much fun, we could do it for hours! When you’re finished exploring, head on back to return your bike, and treat yourself to some ice cream at Jeni’s Splendid Ice Cream. This place is hands down my favorite ice cream shop… dare I say, ever? The flavors are so unique, I wish we had it up here in NYC! Between the two of us, we tried the wildberry lavender, brambleberry crisp, ricotta toast with red berry geranium jam, frosé, cookies and cream, and salted peanut butter with chocolate chips. Our favorite was definitely the lavender!

For dinner, be sure to make a reservation ahead of time. We forgot to do so and didn’t want to wait an hour because we were starving, so we ended up grabbing a quick bite at Xiao Bao Biscuit. While it wasn’t one of our favorite places to eat, the cabbage pancake was pretty good and the most popular item on the menu.

Sunday

Have a chill Sunday morning picnic at Hampton Park. This is the perfect place to pull out a blanket and relax under the peaceful Spanish moss trees. There are also tons of blooming flowers and nature paths for visitors to enjoy.

For lunch, head on over to either Leon’s or Darling Oyster Bar. Leon’s is a bit further out from city center but they’re known for their fried fish and chicken sandwiches. Darling Oyster Bar is located on central King and… well, the name itself says it all.

After lunch, it’s time to visit the iconic Rainbow Row! Explore the Battery and surrounding neighborhoods, where there are cute houses and flowers galore. Fun fact: we actually ran into Julia of Gal Meets Glam shooting on the street. I had a total fangirl moment and completely made a fool of myself, ha!

And of course, what’s a trip to Charleston without at least one traditional sit-down Southern dinner? Poogan’s Porch is the perfect place to enjoy a quiet Sunday evening meal. The shrimp and grits are amazing and I highly recommend it.

If you can, try and get a table out on the balcony! Enjoy the fresh air and view of the millennial pink Wyndham Mills House Hotel.

Monday

On your last day in Charleston, head back into town and cross any remaining items off your bucket list! Explore the surrounding neighborhoods and nature if you have time. Stop by The Daily for some fantastic breakfast to start off your day. We ordered the avocado toast, smoked salmon toast, oatmeal cookie latte, and almond milk latte — all were delicious!

We especially loved Candlefish, a charming little candle shop off of King Street (sign up for a candle making workshop if you can!), and John Rutledge House Inn, which had the cutest stairwell and balcony.

And that’s all for now! I hope you enjoyed this guide. 🙂 If you have any local favorites or insider spots, let me know in the comments below. I’d love to come back again someday!