Charleston Weekend Recap: My Favorite Spots & Recommendations


Spoiler alert: my weekend away in Charleston, South Carolina was absolutely incredible. I’m officially obsessed with the history, the culture, and of course the food that the beautiful city has to offer. I’m sharing all the details from my Charleston weekend, and in case you haven’t caught on, I’ll definitely be planning another trip back.


Ryan and I stayed at the Mills House Wyndham Grand Hotel. I did quite a bit of research before booking, and ultimately chose the Mills House based on location. We definitely wanted to stay in the Historic District, and the Mills House was literally in the middle of downtown scene.

I would be completely lying if I told you guys that we planned a bunch of activities to do each day. Instead all we wanted to do was explore the city and relax. It was pretty chilly for Charleston; each day was only in the mid-high 50s, (but let’s be honest, anything is better than the frigid Chicago weather.)

Instead each day we woke up, went to breakfast, then walked around the city until lunch. Between the shopping and the historical sites, there was plenty to see. After lunch we’d keep walking, around hang at the hotel for a bit, then head to dinner for the night out. One of my favorite parts about our Charleston weekend was that we didn’t take a cab or Uber a single time. Everything was in walking distance. Don’t get me wrong, I completely regret not packing comfortable walking shoes, (like these, these or these) but after the first day my feet were too numb to feel anything.


As for historical sites, Rainbow Row was definitely one of my favorite places, and the Old Slave Mart Museum had us absolutely speechless.

I really wish we would have had time to visit the Boone Hall Plantation and Magnolia Plantation and Gardens, but I guess that means we’ll just have to go back for another Charleston weekend!


Okay before you judge us, Ryan and I wanted to try out as many bars and restaurants as possible. So we’d have a drink (or a few 😉 ) at each spot, before moving on to the next one. Below is the list of spots we visited.

Restaurants We Ate At:

Virginia’s On King –  We went to Virginia’s for breakfast on Friday morning. It was so adorable and their food was incredible. Their home fries and omelets were out of this world.


Prohibition – A great lunch spot, but even better for late night drinks. They have live music and amazing cocktails. The bar was super rustic with the coolest prohibition posters and decor.

Charleston Crabhouse – This local hot spot has amazing seafood. Ryan is still raving about the crab house steampot. Yes, the food was fantastic, but my favorite part had to be the Bloody Mary’s. They were super spicy, and honestly the best I’ve ever had!


Halls Chophouse – If you visit Charleston you absolutely have to eat at the Chophouse. They have the best steaks and seafood you could ever want. Plus, their Sommelier was able to help us pick the most amazing wine.

Craftsman Tap House– We went to the Craftsman the first night for a casual and low-key dinner. They have great pizzas and even better craft beer flights.

Cypress – We went to the Cypress for our last dinner. The restaurant itself was absolutely stunning. I would recommend stopping in for an appetizer and a couple drinks rather than having dinner here. I don’t want to bash the food, but I think the food was so delicious at the other restaurants that you’d be better off eating elsewhere.

Places We Drank At:

The Blind Tiger – Old school vibe, with the best mules.

Lagunitas Brewery – We were shocked to see a Laguintas Brewery in Charleston! Laguintas is one of our favorite Chicago breweries. We usually keep a keg of A Little Sumpin’ Sumpin’ on tap in the basement bar ;).

Tommy Condon’s – You can never go wrong with an Irish pub. They have great local beers on tap!

The Barbadoes Room – This is the restaurant within the Mills House. The cocktails were the perfect combo of dangerous and delicious.

82 Queen – This was the coolest hidden bar. You can only access it from the alley. I’d love to go back in the Spring to enjoy the courtyard patio.

Closed For Business – Rated as one of the best bars in Charleston. To be honest, I wasn’t really impressed. It was super crowded, and very loud. (What, am I 80?) It was cool to grab a drink here, but you couldn’t have paid me to stay much longer.

The Belmont – This was one of my favorite bars. It has an old Hollywood feel, and they play old black & white movies on the projector. It’s super intimate and the drinks were obviously great too.

The Kingdom – This bar actually just opened. The grand opening will be Valentine’s weekend. They had an amazing mule made with Jameson whiskey. I was hooked. The decor was amazing – lots of golds, furs, etc. basically all my favorite things.

Mac’s Place – Last but not least, Mac’s Place. This is a completely Chicago-themed bar. We felt right at home as we sipped on 312 and snacked on wings. This was totally casual but definitely one of my favorite spots we found during our Charleston weekend.

I’m still in denial that we had to leave Charleston. But I can’t wait to plan my next trip!



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