Charleston Recommendations

This is a major photo overload post. I tried my best to narrow it down and considered breaking it up into multiple posts, but I wanted everything to be in one spot.

A couple of weeks ago, my friend Alex asked if I would be in Charleston. She’s the owner/designer behind one of my favorite brands, Persifor, and they were hosting a lunch down there. I looked at the dates, didn’t have any conflicts, and had enough JetBlue miles to book the flight for free so I decided to go for it. At some point, I told Kiel and Sarah I would be there, and they decided to make the trip down as well to put some finishing touches on their space in Skinny Dip.

Where to stay in Charleston

I spent a few minutes looking online at hotels and ended up booking the last room available at 86 Cannon. I had seen it all over Instagram (where else?) and knew how cute it looked. It’s a five-room boutique inn… and it may be my most favorite hotel in the entire world now.

I normally prefer to stay in larger hotels where you can come and go completely under the radar. With only five rooms, I knew that wouldn’t be the case at 86 Cannon, but the owners are so wonderful. I loved waving to them as I walked in for a rest in the afternoon and stopping to chat in the morning before heading out and giving their two dogs (Gus and Sully) belly rubs on the porch.

86 Cannon

It’s hard to believe, but as great as it looks in pictures, it’s even better in person. The room I stayed in was on the second floor, right off of the piazza. In fact, the door opens up to the porch– the perfect place to enjoy your morning coffee or relax during a rain storm.

I had the hardest time leaving every morning because I felt so relaxed. I wouldn’t have minded spending my entire stay there and just ignoring the whole city, which is saying something.

86 Cannon Charleston

Charleston Hotel Recommendations

I was supposed to have three days in Charleston, arriving early Tuesday morning and leaving late Thursday night. However, I ended up missing my flight in the morning. (I went to the wrong airport!!! Who does that? I was just in auto-pilot mode I guess!) I spent the whole day Tuesday sitting in the airport working, and when I finally got to Charleston, I was so tired. I met up with Kiel and Sarah, and we ran some errands and just hung out really. Nothing too exciting.

I took things slow on Wednesday morning. It was pretty rainy in the middle of the day, so I popped in to get my nails done before heading over the Persifor lunch at the Dewberry. The food was amazing; I had a delicious strawberry tomato soup that I’m still thinking about. It was also the perfect opportunity to get to see so many of my Charleston friends.

Persifor Lunch

Kiel, Sarah, Dave, and I were hosting a little meet and greet at Skinny Dip at 4:30, so after lunch, I had to run back to the hotel to change and get ready. If you’re in Charleston, you have to swing by Skinny Dip! They originally had a summer pop up on Nantucket and opened a full store in Charleston this month. It’s brimming with amazing brands, including an entire room of KJP products.

Kiel James Patrick Charleston

Skinny Dip Charleston

Charleston Shopping

There’s more upstairs, too, including a wine and coffee bar. My friend Ashley (of Ashley Brooke Designs) did all the mugs and coffee sleeves!!! How cute?!?!?

Ashley Brooke Designs Charleston

Skinny Dip

The little oasis of a back patio!

(And apparently, this is where I segue into food.)

After the meet and greet, the four of us met up with Thomas (Julia’s husband) for dinner at Leon’s. I have no pictures, but you have to put it on your list of dinners if you go to Charleston. It’s designed to look like a southern dive restaurant. The food was so good. Sarah and I shared Brussel sprouts, hush puppies, and fried chicken. YUM!! Julia and Chassity met us there after dinner, and we caught up a little before leaving for bed.

Callie's Hot Little Biscuit

I had the entire day to myself on Thursday. My plan was just to explore, shop, and eat. Not bad. I started at Callie’s Hot Little Biscuit. These are just the best little biscuits ever.

Then Julia, Thomas, and Chassity and I had lunch at Park Cafe. It was such a great lunch. We were able to sit outside and relax in the warm air. (The mug with that weird little brown thing is mine; it was a super delicious lavender fog with a toasted marshmallow!)

The Park Cafe

I had to walk off all the calories from the fried chicken, biscuits, and burgers. And where better to do that in historic downtown Charleston? I could walk there admiring the gorgeous houses all day every day. It didn’t even matter that I was breaking in new shoes (the worst idea I’ve ever had, in case you’re wondering) and getting sunburned (another not-great idea). I just kept telling myself, “one more block!”

Charleston Door  Charleston House    Rainbow Row Charleston   Sugar Bakeshop

I swung by Sugar Bakeshop which was right down the road from 86 Cannon. I got a cupcake to enjoy right then and a cookie for my flight home. I sadly had to grab my luggage and hop in a cab to the airport.

As much fun as it is to visit new places, I do love revisiting cities I’ve already been. It’s nice to know the lay of the land already and not to feel so rushed to try to see and do everything. I definitely see more trips to Charleston in my future.

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Charleston itself is pretty bustling with tourists! I wouldn’t say it’s quiet exactly. BUT there are great neighboring beach towns you could go to an pop into Charleston for a fun afternoon.


Agreed that it’s not exactly a quiet city! If you’re looking for a quiet town close by, go to Mount Pleasant and drive/Uber into Charleston! (I live about 3 hours from Chuck Town and go there often for weekend getaways/bachelorette parties!)

Great recommendations! Will have to try those restaurants next time!

Jen Kessler

With that amount of Charleston going around IG lately, I have been having such the urge to visit! It looks amazing and your photos of it are beautiful!


Such great photos! I’ve been wanting to stay at 86 Cannon since I saw it was added to Tablet’s hotel collection. Zero George was a great place to stay also. Seems like everything is blossoming more in the south than up here!


I’ve been hearing so many great things about Charleston lately! It looks unbelievably beautiful in photos! I don’t think I’ve ever seen a town that was so Pinterest perfect!



I just missed your trip – I arrived Thursday night and just got home this morning. Wish I’d been able to attend the KJP event at Skinny Dip. But you’re right, Charleston is wonderful!


I can’t WAIT to get back to Charleston soon and check out Skinny Dip! Living there for three years after college was one of the best decisions I ever made and I hope to move back there someday soon! I so miss the days of wandering around the street South of Broad and popping into all of the yummy foodie spots!


Hi Carly,
Did Charleston fare ok in Irma? We were going to visit over Christmas. Is that a good idea?