Now that our kids are getting older and have busy lives of their own, I treasure any time we have all five of them together. Since they were little guys, we’ve always taken a week during the summer for a vacation. This year, we asked the kids where they would like to go and they answered unanimously “Charleston.”
We have been to Charleston before, but never as a whole family and never as the actual destination for our vacation. It’s been a pass through for our visits to Myrtle Beach or Hilton Head. So I was over the moon that Charleston was going to be our home base this year.
August is probably one of the hottest months to visit Charleston. The heat and humidity is no joke. But for born and bred Midwesterners, it’s not that different than Chicago summers. We could handle it.
Because we were limited to less than a week due to our boys’ college football schedule, we opted to fly. This was such a treat because the flight from O’Hare to Charleston is less than two hours. We’ve made the 14-hour drive to South Carolina before and it’s totally doable. But like I said, it felt like a real vacation to get on the plane.
Where We Stayed
Charleston is filled with a number of incredible hotels and home rental possibilities. The list is endless. But I was thrilled to find out my husband booked us at the French Quarter Inn.
It’s been a long time since I stayed somewhere so nice, especially since we were traveling with all of the kids. But some of the perks that made the hotel so special actually ended up saving us a little money, too. For example, the French Quarter Inn is so perfectly located that you can get away without renting a car or even taking any Ubers. We walked everywhere and it was wonderful! The Inn also provided a full complementary breakfast, afternoon snacks and cocktails, and late-night dessert every day. Feeding our crew is no joke, especially in an expensive city like Charleston, so these extra meals came in clutch for my kids. And, all of the luxuries of daily room cleaning and turn-down service were back in this post-pandemic world of ours and it was heavenly. Highly, highly recommend this hotel if you’re looking for somewhere to stay in Charleston with just the nicest people watching over your stay.
What We Did
We really tried to balance having enough to do and time to relax on this vacation because we all really needed a little break. We’ve been very guilty of overscheduling ourselves in the past, so I’m happy to report we got it right this time around. Here’s what we did.
Bike ride thru Charleston and around The Citadel.
Self-guided bike tour of Charleston: We rented bikes for the whole gang at Bilda Bikes on King Street. It was incredibly affordable to rent bikes for the day. The shop owners gave us a map with a good route of the city and surrounding areas. Downtown Charleston isn’t bike friendly, but if you venture just a block or two out of the busy city streets you’re good to go. We were able to get a great lay of the land, including visiting some of the beautiful parks, the Citadel, Rainbow Row, and the Battery. Additionally, I made the kids help me find Miss Patricia’s house from the Bravo TV hit show Southern Charm. (If you know, you know!) It was awesome! Everyone said our bike trip was one of their favorite things we did.
Visit Fort Sumter: We didn’t do this on this trip to Charleston because we had done this on a past vacation. But t’s kind of one of those boxes you have to check if you’re in Charleston. It’s fun ferry ride out to this historical site and the guides do a great job giving you a little piece of southern history.
Spent an Afternoon at the Beach: We ventured over to Sullivan’s Island for a little beach time and reprieve from the heat. We did have a rental car, but a short Uber ride may be even easier so you don’t have to worry about parking. It was a little windy the day we visited, but the water was warm and a nice break from the heat. The beach wasn’t overly busy, so it was very easy to stake out a spot for a couple of hours.
Chartered a Sailboat: My kids fancy themselves as boat people. Not sure how this happened, but spending a couple of hours on the water has become a staple for our family trips. We chartered a sailboat through Avanzar Charleston for a tour of the Charleston Harbor. We had a wonderful captain, equipped with a number of historical tidbits, and a readiness to turn the music selection over to our son Eddie. It was a wonderful afternoon.
Day trip to Kiawah: My brother and his wife love Kiawah and suggested we check it out if we were looking for something to do. It’s only about an hour away from Charleston, but it is a world unto itself. I have a hunch a trip to Kiawah is likely in our future. On the day we visited, we only had time for lunch at the Ryder Cup Bar. But from what we did see, the views were magnificent.
Golf: There are plenty of courses to golf and the boys took an afternoon to do this while the ladies shopped (more on shopping below). The boys went to Patriot Point to golf. I don’t think it was the most picturesque course, but it was perfect for our amateurs to shoot around.
Where We Ate
It is very much the Charleston thing to eat well. Be prepared to make reservations pretty far in advance and just know that there is no rushing through a meal.
Millers All Day: This was the first place we ate upon arriving in Charleston. Located on King Street, this one-time pharmacy has something on the menu for everyone.
Sweetwater Cafe: Just down the street from our hotel, this was just good old fashioned diner food.
Another Broken Egg Cafe: If you’re a local to the midwest, this restaurant reminded me of Egg Harbor Cafe. It was a great place for quick bite, again…very close to the French Quarter Inn.
Glazed Gourmet Doughnuts: Of course I made my family go here! Glazed rotates their homemade donut flavors daily, so you could visit every day and get something different (not that I did, but the thought was tempting).
Vicious Biscuit: We knew we were in for a treat when we had to wait in line for 45 minutes just to get in the door. They have every kind of biscuit concoction you could dream up and we all agreed that these were the best biscuits we had on vacation. I have made it my personal quest to taste test biscuits and gravy across the country and their recipe was the very best I’ve ever had. They use maple sausage in their gravy and that is everything!
The Obstinate Daughter:This may have been my favorite restaurant of all those we ate in Charleston. Located on Sullivan’s Island, its beachy vibe and delicious food makes any meal feel like a vacation. An absolute must for your trip!
Frannie & Fox: A very fun and festive atmosphere located in the beautiful Emeline Hotel. You’ll likely run into a bachelorette party or two (we saw three the night we were there!), but the food and service will make everything else fade into the background.
Vincent Chiccos: We ate our favorite dinner in Charleston here. The food and service were just a step above everyone else. A must!
Little Jack’s Tavern: This little old-time tavern is a little outside the city center, but if you’re in the mood for an amazing burger, this is the place.
Le Farfalle: This upscale Italian eatery came highly recommended and didn’t disappoint.
I heard the most amazing things about Chubby Fish but we never made it there. If you can go, please do and let me know how it is!
Some of our kids would get up in the morning and work out on vacation, but my daughter and I would walk for coffee. We could have stayed another week and still not hit all of the spots, but it would have been fun to try. Here were some of our favorites.
Babas on Cannon: Rumor has it their off-menu tacos are the best. We didn’t get to try but plan to on our next visit.
Harken Cafe: We had to go to this cafe twice…darling space and amazing baked goods made on the premises!
Bitty & Beau’s: Wonderful coffee and the cafe employees people with disabilities–so much good!
Roof Top Bars
We tried to squeeze couple of these in while we were in Charleston. I don’t drink any more and am happy to report that Charleston’s “mocktail” game is the real deal. Nearly every rooftop bar we visited had a handful of mocktail recipes at the ready. Most rooftops have age restrictions after 10 p.m. (you need to be 21 to get in), so we visited these before dinner.
The Vendue: The kids loved this one. Very casual and fun atmosphere, great appetizers.
Fiat Lux: Classic, old-world Charleston–very elegant. My personal favorite rooftop on top of the Hotel Bennet.
Off Track Ice Cream: So good, we went back twice! Their chocolate fudgy brownie may have been the best ice cream I’ve ever had. All ice cream is made in-house and their menu of vegan ice cream (which was a hit with my daughter Grace) is even more extensive than their traditional flavors.
Charleston’s King Street has EVERYTHING. And when I say everything, I mean EVERYTHING! Every retailer from Target to Hampden Clothing has a spot on this illustrious street. Here were some of our favorites to visit:
Madison Mathews: This shop is a must. If the Charleston aesthetic could be summarized in one store, Madison Mathews is it. They also have an incredible website with all of their offerings and were kind enough to give me a code to share. Enter ANNMARIE at checkout and get 10% off your purchase.
It was an amazing trip and we can’t recommend Charleston enough! Please let me know if you have any questions or additions. I’d love to know them.
Happy travel planning!