Charleston Weekend Travel Guide

Charleston, South Carolina has been “up next” on my travel list for way too long. Thankfully, the wait is over and I finally got to experience the Holy City. I’ve broken down my recap into four main parts: outfit details, where to stay, where to eat, and what to do. Enjoy!


Top: Similar here || Skirt: Tanya Taylor

Top: Free People || Shorts: Free People || Shoes: Steve Madden

Dress: Christian Pellizzari || Shoes: Similar here

Top: Similar here || Pants: Articles of Society || Bag: Mar Y Sol


We stayed at 86 Cannon for our weekend getaway. This quaint Boutique Inn is in the Cannonborough district of Charleston just a few blocks from iconic King Street. When we pulled up I was immediately in awe. The house is stunning and the architecture is stately and southern. Upon arrival, we were greeted with champagne and given a tour of the property.

Our bedroom opened up to this front porch – can you say #goals? Every detail was done to perfection. From the plantation shutters, to the exposed brick fireplace, there were so many modern yet authentic details that were effortlessly southern coastal.

Every morning continental breakfast is served and in the evenings a complimentary wine and cheese pairing is served in the cafe. The owners are super helpful and communicative. They gave us so many great ideas for activities and made sure that our stay was absolutely perfect. We will definitely be back to 86 Cannon!


Charleston is a gold mine for foodies and it did not disappoint. We had so many places we wanted to try but couldn’t get to them all. I guess that means we’ll have to come back! Key: Make sure to book your reservations as far in advance as possible. A lot of the popular restaurants are fully booked 2 months in advance.

Little Jack’s Tavern – We landed at this spot after getting tired of waiting for a table at Leon’s Oyster Bar. Super cozy, tavern style restaurant with delicious food. Definitely recommend the Tavern Burger and the Herb Parmesan Fries.

Leon’s Oyster Bar – This is a low-key spot with amazing no-frills southern fare and seafood. You’ll want to get a reservation as this place is always packed. The fried chicken and scalloped potatoes were heavenly. They also mix up some pretty killer cocktails!

The Macintosh – Farm-to-table style restaurant with a James Beard award-winning chef. You know a place is good when the salad makes you want to lick the plate – the SALAD, yes you read that right. The CAB Deckle was to die for and the bone marrow bread pudding was unlike anything I’ve ever had. You can’t leave without it.

Jeni’s –This ice cream shop has so many amazing flavors its hard to choose. But one reigns supreme – Brown butter almond brittle in a waffle cone. Say no more.

Xiao Bao – Delicious Asian soul food spot that will knock your taste buds off. This place is super close to 86 Cannon and has a really unique vibe. The Japanese cabbage pancake was surprisingly phenomenal and the fried rice was seriously some of the best food I have ever put in my mouth. Must try!

Husk – Another farm-to-table style restaurant in the heart of Charleston featuring a James Beard Award winning chef. The menu changes daily and all ingredients are locally sourced. We had the fried chicken skins with pimento cheese ranch to start and we were blown away. For mains, we had grouper and steak. Both were good, but not overwhelmingly delicious. We had the Rhubarb tart for dessert and it was disappointing. The drinks however, were outstanding! This is one of the most highly recommended restaurants in Charleston, but all in all we weren’t super impressed. Maybe it was an off night?

Sugar – This sweet little bakeshop is just a few steps away from 86 Cannon. It is overflowing with character and delicious treats. The vanilla blueberry cupcake was insane and the cookies were unreal.

The Daily – On our last day we stopped at this little shop for a grab-n-go bite and coffee. The pimento cheese English muffin was SO good. While you’re here make sure to get a coffee with almond milk – it’s homemade!

Other places we wanted to go:
Poogan’s Porch
Chez Nous
Obstinate Daughter
Butcher & Bee


Explore Rainbow Row – It’s even more adorable in person. Major photo op!
Shopping on King St – You haven’t been to Charleston if you haven’t shopped on King.
Charleston City Market – A bit touristy, but super fun. It’s mostly sheltered, so it’s a great activity if you happen to be in the city on a rainy day.
Take a pedicab around South of Broad – Our BnB owners gave us this recommendation and we were so glad. We went at night and got to see all beautiful mansions lit up – so cool!
Ride bikes through the city – This is the best way to see Charleston. We rode bikes provided by 86 Cannon to Colonial Lake down Battery and back. We saw so many pockets of the city and really felt like locals!
Charter a boat – We did a private sailing charter with OM sailing and had a blast! The owners at 86 Cannon packed us a little beach bag with towels for our trip. Before heading to the harbor to set sail, we stopped at Caviar & Bananas for wine and a cheese board. The boat was beautiful, clean, and huge! We did 3 hours and got to see the harbor, Sullivan’s Island, Fort Sumter, and the Ravenel Bridge. Although pricey, totally worth the expense. It was one of the highlights of our trip!

Charleston is truly such an incredible city. It is bustling with history, charm, and beauty around every corner. If you’ve been, let me know what you think about Charleston in the comments below!


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