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North America · September 13, 2021

How To Spend A Perfect Weekend in Charleston, South Carolina

Charleston is by far one of the most charming cities I’ve ever had the pleasure of visiting. It was founded in 1670 which can begin to tell you how rich its history is. And it’s definitely one of those places that will make you feel as though you’ve stepped back in time- with its cobblestone streets, horse-drawn carriages, and incredible antebellum-style homes. It’s a perfect destination for a weekend getaway.

 If you’re not impressed by the southern charm that you can almost feel in the air, maybe the gorgeous architecture will get you, or possibly the incredible food! Not to mention, the weather is perfect almost year-round.

Charleston was at the top of my personal bucket list for years! I finally made the trip back in April of this year and it met every expectation I had. If you’re looking to have a fun-filled weekend in one of the most unique cities in South Carolina, here’s a Charleston weekend itinerary you can’t go wrong with:

Table of Contents

Toggle
    • Other Fun US City Itineraries To Check Out
  • Friday Charleston Itinerary
    • Stop 1: Poogan’s Porch
    • Stop 2: The Battery
    • Stop 3: White Point Garden
    • Stop 4: Check into Accommodation
    • Stop 5: Hymans Seafood
  • Saturday Charleston Itinerary
    • Stop 1: Take A Walk Through the Historic Charleston City Market
    • Stop 2: Breakfast at Callie’s Hot Little Biscuits
    • Stop 3: Joe Riley Waterfront Park/ Pineapple Fountain
    • Stop 4: Rainbow Row
    • Stop 5: Fleet Landing
    • Stop 6: Mason’s Famous Lobster Roll
    • Stop 7: Old South Carriage Tour
    • Stop 8: TBonz Gill & Grill 
  • Sunday Charleston Itinerary
    • Stop 1: Isle of Palms
    • Stop 2: Departure

Other Fun US City Itineraries To Check Out

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Friday Charleston Itinerary

Stop 1: Poogan’s Porch

After arriving in Charleston, you should make your first stop an unforgettable one and head to Poogan’s Porch for lunch. This previous Victorian home, which was built in 1891, was converted into a restaurant in the 1970s. It still holds all of its original charm making for a unique dining experience. The menu features delicious southern fare and the food is really out of this world. I would highly recommend the chicken and waffles. Check out their menu here.

Stop 2: The Battery

After enjoying your first Charleston meal, it’s time to take in some of the sights. A great place to start is The Battery, located right in the heart of Charleston’s historic district. The Battery is a very important landmark in Charleston. It was built as a defensive seawall and stretches along the lower shores of the Charleston peninsula. Today it’s a lovely promenade perfect for taking a scenic walk and admiring all of the incredible antebellum homes along the water. They are absolutely mind-blowing!

Stop 3: White Point Garden

Here, you will also stumble upon White Point Garden, a 5.7-acre public park located right near The Battery. Stroll under the large shady oak trees and enjoy the ocean views. Throughout the park, you will find historical statues, civil war cannons, and a beautiful gazebo, perfect for photo ops.

Stop 4: Check into Accommodation

By this time you’ll surely be able to check into your accommodation if you haven’t already and take some time to get settled in. We opted to stay in a beautiful Airbnb just a few minutes outside of the city. It was a quiet, peaceful neighborhood, and the apartment was very spacious.

Charleston has numerous options when it comes to accommodations within different price ranges. There are excellent hotels and B&B’s right in the middle of all of the excitement and Airbnb options are plentiful.

Stop 5: Hymans Seafood

After getting settled into your home for the weekend, it’s time for dinner. Head on over to Hyman’s Seafood for an incredible meal- but be prepared to wait for a table. Hyman’s is walk-in only and due to its popularity, there’s almost always a wait. The wait was definitely worth it though! There are some great signature platters right on the menu, or you can even build your own. The seafood here is extremely fresh and so delicious! Pretty cool side note: every seat at each table has a plaque of a famous person that has sat and eaten at that very seat! Check out their menu here.

After dinner I’d suggest taking a nice evening stroll, stopping in one of the many Charleston bars for a drink, or having a relaxing night in to recharge for the next day ahead.

Saturday Charleston Itinerary

Stop 1: Take A Walk Through the Historic Charleston City Market

Start your day off with an exciting walk through the Historic Charleston City Market. Stretching over four blocks, this bustling market holds everything from souvenirs, crafts, woven baskets, jewelry, clothing, sweets, artwork and so much more! It is by far one of the most visited places in Charleston and is definitely worth walking through. It’s open daily from 9:30 am- 5:30 pm and is free to enter.

Stop 2: Breakfast at Callie’s Hot Little Biscuits

Right inside of the Historic Charleston City Market, you’ll stumble upon Callie’s Hot Little Biscuits, the perfect place to grab a quick and delicious breakfast. They serve a variety of different biscuits and have a little something for everyone. I personally tried the bacon egg & cheese biscuit and the fried chicken biscuit. They were both delicious. 

Stop 3: Joe Riley Waterfront Park/ Pineapple Fountain

After fueling up, head on over to Joe Riley Waterfront Park. This beautiful eight-acre park is located on the Cooper River. Here you will experience lovely views of the water, tons of green spaces, beautiful shady oak trees, and park benches to relax on. Joe Riley Waterfront Park is also home to the famous Pineapple Fountain- a must-see when visiting Charleston. This beautiful fountain was created in 1990 and has been a staple for photo ops and visitors ever since.

Stop 4: Rainbow Row

From Joe Riley Waterfront, head on over to Rainbow Row. This series of 13 brightly-colored houses is one of Charleston’s most photographed spots! These homes were originally constructed in 1740 but didn’t get their pastel colors until the 1930s. If you’re hoping to get photos in front of Rainbow Row my piece of advice- have some patience. There are always people walking past and others waiting to take photos. Be a little patient and a window will open where you can snap some shots! 

Stop 5: Fleet Landing

By this point, you may be needing a drink break or a little snack. Stop at Fleet Landing, which is an awesome restaurant & bar located right on the water. They have delicious signature cocktails- I’d highly recommend the pomegranate mojito. Along with a great menu of fresh seafood, salads, sandwiches, and southern fare. The oysters were out of this world! Check out their menu here.

Stop 6: Mason’s Famous Lobster Roll

Hopefully, you save a little room, because up next is lunch! If you’ve never had a lobster roll before then Mason’s is a great place to go for your very first one. And if you’re anything like me, which is a lobster roll connoisseur, then this one will not disappoint! Mason’s is a small shop, where you walk up to the counter to order, and you can either dine-in or take out. I’d highly recommend the Connecticut roll, which is tossed in butter and served warm. Check out their menu here.

Stop 7: Old South Carriage Tour

There’s no better way to experience a new city than by taking a guided tour. Old South Carriage Tour Co. offers day and night/ carriage and walking tours, depending on your interests. You’ll be able to learn all about the incredibly rich history of Charleston from a certified tour guide while taking in the beautiful views! Tours are offered from 9 am – 5 pm, leaving every 15-30 minutes and last one hour. Check out their website here.

Stop 8: TBonz Gill & Grill 

When it comes to dinner, Charleston’s options are endless. We actually stumbled upon TBonz by accident and it wasn’t actually our first choice. But we couldn’t have been more satisfied with our meal here. The atmosphere is fun but casual and the menu has a little something for everyone. They are known for their signature steaks, which you really can’t go wrong with! But they also have fresh, local seafood dishes and low country specialties. Check out their menu here. One of my favorite parts of TBonz is that it’s connected to Kaminsky’s Dessert Cafe. Their desserts are made fresh daily and they always have something new. The coconut cream pie was outstanding!

Sunday Charleston Itinerary

Stop 1: Isle of Palms

For your last day in Charleston, I suggest venturing out of the city to see what the surrounding areas have to offer. Just about 40 minutes outside of Charleston will bring you to the Isle of Palms. Nestled between the Atlantic Ocean and the Intracoastal Waterway, you’ll find yourself on the most beautiful beach. Either pick up something to eat on the way or pack a little morning picnic and get an early start. Being on the beach is a perfect way to end a weekend getaway.

Stop 2: Departure

This brings us to the end of our Charleston weekend itinerary. I hope this offered up some great ideas for your own Charleston trip. If you have any questions or comments please leave them below and as always, happy travels!

Posted In: North America

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I'm Carly! A New York State based traveler that loves exploring the world as much as my own backyard. I'm here to share helpful tips and itineraries as well as to inspire you to enjoy the beautiful world around us.
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