Vaca with the Monaghans – Charleston

Hi Friends!

Sometimes in life everything just lines up at the exact right time. The cosmic stars align in your favor. And that’s just what happened for TJ and I this past week. To explain though, I’ll need to backtrack just a bit…

Originally TJ and I had planned a week long honeymoon to visit Paris and London (my dream trip) over the week of April 28-May 5. It was my one week off between spring and summer semesters in school and the weather in Europe is supposed to still have a slight chill but be beautiful. Well, while all those things remained true, TJ and I had been invited to a friends wedding in Jamaica that is set for September 17th of this year. We decided that financially it just wasn’t responsible for us to take two out of the country trips in one year (we are on Dave Ramsey baby step #2 after all). So we put a pause on that honeymoon trip and decided to save it for 2019. In the last month I received a promotion at work and TJ accepted a position at a new law firm in the last two weeks and these things helped us in a big way with a schedule opening. Luckily for us, TJ didn’t have to complete a full two weeks at his prior law firm and we were able to take a last minute vacation on the one week I had off from school, the week we were supposed to go to Paris and London.

When we realized we would have this week together to take a trip we started trying to figure out where we should go. In the end we decided on a drivable location. Two drivable locations actually. We settled on Charleston, South Carolina and Asheville, North Carolina. I started looking into hotels (we were only two days out from our trip when we planned it) and after seeing the costs per night in those places I decided to research Airbnb. Once I realized it would save us $400 on our trip, I booked us two nights in Charleston and two nights in Asheville. And let me tell you what, our first Airbnb experiences were certainly not our last!


Seriously, how adorable was our little place in Charleston?! It was located close to restaurants and bars and in an old Charleston building that has been converted into little condos. We only ended up having less than a day and a half in Charleston because we arrived around 7:30pm on Monday. After a quick change and refresh, we headed out for dinner. Luckily for us, TJ has a friend that now lives in Charleston and was able to give us some recommendations. Plus, I reached out on instagram and Facebook for everyone’s favorite restaurants, activities, and sights to see in both Charleston and Asheville. This is something I would always recommend doing before you take a trip. We got a lot of repeat suggestions which let us know those were definitely must-hit spots. But we also got some that were just one-offs (spoiler alert: one of those ended up being our FAVORITE dinner spot)!

For our first night we chose a more casual night out. For dinner we took a short uber ride down to King St. to Little Jack’s Tavern. The food menu is short and the drink list is long. Not a bad place to be! It was intimate and cozy, yet relaxed and welcoming. We loved the vibe as well as the food. TJ is more adventurous in the food department so he tried a duck liver mousse as an appetizer and a crab roll for his meal. He said they tasted fresh! He washed them down with a brown derby. Or as I like to call it, a fancy bourbon drink. I’m probably one of the world’s pickiest eaters so I stuck with something classic that I knew I would enjoy. I did their bar steak (a 6oz sirloin) with asparagus.

After we finished up dinner we took a short walk down King St. to a fun little dive bar called Recovery Room (another suggestion by TJ’s friend). We had plans of bar hopping to different dive bars throughout the night but the Rec Room (as it was referred to by locals) had all the elements for a good night so we ended up sticking around. All night. The bar had cheap drinks, fun games, and someone selecting good music off the juke box. We battled it out in pinball, Buck Hunt, shooting hoops, and pool. I didn’t win a single event. I did at least hold my own in the hoops department though!

So much fun was had that first night that waking up Tuesday morning to start our exploring got off to a VERY delayed start. Like alarm set for 8 am but you don’t roll out of bed till around 11:30 am kinda delay. Oops. We showered and headed out for adventures. But first, we had to make a stop for some hangover food and what better place to do that then on the water? We visited Red’s Ice House and enjoyed a pimento cheese appetizer followed by grilled chicken for me and blackened grouper for TJ. If you’re in the area and looking for a relaxed water view deck with some good eats, stop in!image

Finally we were able to head to our destination for the day, Boone Hall Plantation. A historical site with beautiful views, it’s a must when in Charleston. While not all the past is filled with good, it’s awesome to see how this plantation is run today and still contributes to the community with fresh fruits and vegetables.

We had a full day at the plantation so as soon as we got back to the condo we showered and got ready for dinner. We were told that we needed to try out this rooftop bar, Pavillion Bar, for a sunset cocktail that just so happened to be at the top of the hotel where we were having dinner. It’s in downtown Charleston. Let me tell you, the views were amazing!! All the heart eyes! There were no bar spots or tables open when we first arrived so we had to wait it out a bit and even pushed our reservation back thirty minutes but it was all worth it!

At 8pm we headed down to catch our latest reservation at the Grill 225 restaurant inside the Market Pavillion Hotel. This gem was recommended to us by just one person but let me tell you what, it should be on EVERYONES list!! It’s definitely a special occasion type of place as it’s not cheap by any means but it was the best dinner I’ve ever had. And we have been to our share of nice steak houses. I started the meal off with the best French onion soup of my life (the hubs had crab chowder), followed by a 8 oz filet for each of us as our main course with a shared side of asparagus, and then a gluten free chocolate mousse cake for dessert for me and a waiter recommended bread pudding for TJ. To top it off we split a bottle of wine. Couldn’t have asked for better views in Charleston or a better meal!

To end our trip to Charleston we walked a short trip over to an adorable bar with another rooftop view and cool cocktails. Henry’s gives you all the Charleston feels!

There’s so many great places to see, drink, and eat in Charleston. We couldn’t possibly fit them all in to such a short time frame. But we saw enough to know we need to make a trip back with a bit more time to explore. We feel like we got the most out of our trip and we hope our visit and recommendations help you when planning your next trip to visit Charleston, South Carolina!



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