I'm Lisa Kirk, a wife, mama, writer, and founder. Since 2010, Something Pretty has been home to my favorite memories, reflections, and inspirations. Thanks so much for reading!

Our Charleston Trip


When Dave and I planned our 2017 travel, Charleston wasn’t really on our radar. As the year progressed, though, we found ourselves aching for a long weekend getaway for just the three of us, and I threw out the idea of taking the short drive (just about four hours) to Charleston for our anniversary. The timing ended up working out flawlessly, and I can honestly say it’s a trip I’ll always remember. I hadn’t realized how special being on a vacation with Charlie would feel, or how refreshed and rejuvenated I would be after spending a long weekend out of town, in a place that never fails to inspire me. Here’s a (photo-heavy :)) look at what we did!

We arrived on Saturday afternoon, got checked in to our hotel and let Charlie roll around, enjoyed the hotel’s wine and cheese happy hour, and then went to Brown Dog Deli (thanks for the recommendation, Abby!) to grab to-go sandwiches for dinner. We ate on a picnic blanket in a lovely park we had passed–lovely enough that I spotted Lucy Cuneo shooting some fabulous wedding portraits nearby :)

On Sunday, we walked to Mass at St. Mary’s (fun fact: it opened in 1839 and was the first Catholic church in the Carolinas/Georgia) before heading to brunch at Cannon Green. I’m a huge fan of all things Easton Porter Group, and had been to the restaurant when I spoke at a conference a few years ago, but hadn’t eaten there. We were pleasantly surprised to find that brunch there was pretty casual, and Charlie spent the meal happily in the perfectly on-brand green high chair! Our food was fantastic (Dave had a BLT, I had french toast custard, and we split a side of roasted potatoes), and the portion sizes were just right.

Our plan for the rest of the day was simply to explore and soak in the city! It was a gorgeous day, so we walked down to Rainbow Row, relaxed on the rooftop patio of Skinny Dip Charleston (more on that next week), and grabbed a snack at Callie’s Hot Little Biscuit in the Charleston City Market. Our last stop of the day was Caviar and Bananas, and since Charlie had fallen asleep in his stroller, we took our time there, enjoying drinks and a charcuterie board before getting my go-to C&B salads for dinner (spinach, strawberries, hazelnuts, goat cheese, and apple cider bacon vinaigrette–yum!).

On Monday, we ventured out of the city to nearby Sullivan’s Island with two missions: to eat at Obstinate Daughter and introduce Charlie to the ocean! Obstinate Daughter came highly recommended by Emily, and we loved it just as much as she did. The atmosphere was upscale, but relaxed, and we’re pretty sure they were playing one of our favorite Pandora stations (Johnny Cash radio). Our first dance song actually came on at one point and I embarrassed myself getting all teary-eyed, naturally right as our server came to take our order…hey, it was our anniversary weekend after all ;) Back to the food–we split a pasta and a pizza dish, and both were incredibly fresh and delicious.

Out of all the fun things we did that weekend, taking Charlie to the beach was our absolute favorite. We had planned to sit there for awhile, but it was pretty windy, so instead, we spent about ten minutes dipping Charlie’s toes into the waves and taking pictures. He was apathetic about it, but to Dave and me, it felt magical! These pictures are also some of my new favorites. Those legs!!

Back in Charleston, we went out on a long walk, hitting a few spots on my list: Black Tap Coffee, Mac and Murphy (an adorable little paper goods store), and Sugar Bakeshop. En route back to our hotel, we stopped at Charleston Beer Works for a drink outside. As a bit of an anti-climactic end to the day, we grabbed dinner from Five Guys! Charlie was getting fussy and we decided it would be happier for everyone if we had dinner back at our hotel rather than trying to brave a restaurant. Gotta do what you gotta do :)

Tuesday was our actual anniversary! After breakfast, we took a walk to The Cathedral of St. John the Baptist for daily Mass. The cathedral was beautiful, and being there felt like such a perfect way to thank God for these two years and all the blessings that have come with them. After church, we walked through White Point Garden and down the Battery, swung on the swings at Waterfront Park, and then went back to our hotel to check out. With our car packed, we headed out on one more outing for lunch before hitting the road. We really wanted to try 167 Raw, but were disappointed to find that their tiny space didn’t have room for a stroller. Dave suggested we try Poogan’s Smokehouse instead, and as you can see from that glorious skillet of goodness below, it was a hit :)

I have one more post about our trip coming up, specifically covering the coffee shops we visited–we hit a new one every day! :)






  1. What an amazing long weekend trip, Lisa! You three look so happy and relaxed; I bet a change in scenery was such a breath of fresh air. And much deserved!! Charleston is forever my favorite (I was even there for a daytrip yesterday!), and I cannot wait to go with Rob someday soon. My list of places to check out is forever growing! Biking around the city is my favorite way to see it, and I probably dream weekly about the first meal I ever had at Husk. Happiest of anniversaries to you and Dave!! xoxox

    • Lisa says:

      Biking and Husk are two things on our Charleston list that we didn’t feel quite comfortable doing with Charlie just yet, but I hope we do very soon!! :)

  2. Dana says:

    Omg Charlie’s grin!!! This food all looks soooo good! Those churches are beautiful! Glad y’all had such a great time!

  3. mary says:

    So fun! Your trips sound like ours…always planning for the next meal, coffee, and Mass. :D

  4. Yay for travel with bebe!! Charlie looks like he had a blast.. and can I just say how jealous I am that you are only 4 hours from Charleston? I’d want to go every few months!

  5. Bethany says:

    What a fun trip! I love Charleston – my husband’s grandma lives in Folly Beach, so we visit often. We are going there for the Fourth of July, and I’m so excited to have my little girl experience the beach and ocean for the first time!

    Kind of a random question – about what age did you put Charlie in your stroller without the infant insert or the car seat? I’m trying to figure out when my baby is ready for her “big girl stroller,” and I have the Uppababy one as well. :)

    • Lisa says:

      Awww, so fun! Visiting the ocean with Charlie, even for the 15 minutes or so we were there, was so magical. Moments like that have been some of the sweetest of parenting so far!

      We used the car seat until he was about 4-5 months old, if I remember correctly–once he was holding up his head really well. We do still use it sometimes (if he falls asleep in the car or something), but he loves being in the upright seat!

  6. Allison says:

    You make this trip sound so dreamy. Your perspective is refreshing and lovely from my “just get through without a tantrum” perspective when my young family of three go on vacation. I pray I learn from you in this area. :)

    • Lisa says:

      Thanks for your kind comment, Allison! Honestly, I think staying at a very central hotel was crucial to our feeling calm and relaxed, because we knew that if Charlie had a meltdown, we were almost always just a short walk from our hotel :) We also tried to plan a lot of time outside, since he’s almost always calmer outside than in!

  7. Kristina says:

    I have never been to the southern states of the US but I am currently dreaming up a road trip with a friend for next spring. Charleston has always been on the top of my list for must-see places and now I am entirely smitten. Can’t wait to see it for myself one day!

    • Lisa says:

      Oh, how fun! There are so many wonderful spots within driving distance in the Southeast!

  8. Liz LoSurdo says:

    Loved reading about your trip!! It makes me want to go back so bad!! ????

  9. […] (six and counting). Charleston has no shortage of adorable coffee shops, so as my last recap of our recent trip, I wanted to share the ones we […]

  10. […] things about the world has made for the sweetest moments of parenting so far (case in point: his first trip to the beach). Over the weekend, we shared another fun “first” with him by taking him to his first […]


Sign up to receive new blog posts directly to your inbox.

Never miss
a post