I have really wanted to travel to Charleston for a while now, and I am so glad I made it happen. I was really toying with the idea and then kept saying no because of having to figure out someone to watch the kids, having Will adjust his work schedule, checking Penelope out of school, the current state of the economy… it all just felt like too much!
However, one day I was scrolling Instagram and saw Elise’s husband post this on her Instagram account (Elise passed away after a tragic car accident in Mexico in March), and they encouraged people to just #takethetrip if they’re ever able to. Timing will never feel perfect… so if you’re able to, just do it! I immediately felt inspired to take the time to book it and plan it and decided I was going to take my daughter Penelope with me!
I am actually going to lay out this blog post with what we did day by day because I personally think it was the perfect itinerary! People are saying on my TikTok videos that there’s no way I packed in this much in a day with traffic, etc., but I did! We didn’t encounter much traffic, however, that could depend on the time of year you’re going, weekend vs. weekday, etc. We traveled Tuesday-Friday (cheaper flights that way) and didn’t encounter terrible traffic! We also went May 6-9, and I felt as though the weather was absolutely incredible. I am not saying you need to follow this itinerary but it will be helpful to see how we did it!
To start, here is a Charleston Recommendation Spreadsheet filled with people’s recommendations when I asked on my Instagram account. I also added all of them to this Google Maps saved list, which you can view (and possibly duplicate and add your own?)
The spreadsheet has the top hotel recommendations, but we stayed at The Dewberry, and oh my goodness, it was such a beautiful hotel. Truly, every corner was immaculate, and I loved the entire vibe. If you don’t want to rent a car, the Dewberry has complimentary Volvos you can use (first come, first serve) for three hours at a time. However, I found renting a car to be worth it to minimize the risk of not having a car/not getting back in time, etc.
Day 1
We landed in Charleston around 2 pm and drove to check into our hotel, and then headed out to King Street to start exploring. King Street is absolutely incredible! There are so many shops everywhere you look and I could’ve easily spent an entire day there.
After walking around for an hour to two, we drove up to Leon’s Oyster Shop for dinner. We ordered the fried chicken and shrimp roll as well as Root Beer and milkshake. A perfect welcome to Lowcountry!
After dinner, we drove down to The Battery at sunset, which was so beautiful. The homes around that area are absolutely incredible as well!
Day 2
On day two, we woke up, grabbed some Callie’s Hot Little Biscuits, and drove out to Cypress Gardens. It opens at 9 AM, so we were the first ones there and were first to get a rowboat. The grounds are beautiful, so even if you have to wait a little bit, you will be just fine.
Rowing around the trees was a bucket list item for me! It’s the same place where they filmed The Notebook, and it was truly magical. There are alligators in the water, however, the workers told me to be fearful of crocodiles, not alligators, which calmed me… a little bit.
We didn’t do much else at Cypress Gardens (the butterfly museum was a tad underwhelming), so we hopped back into the car and headed towards Isle of Palm Beach. After we swam for a bit, we headed back to the hotel to shower and change, and headed back out to Mount Pleasant to see Post House and the shops next to it. We didn’t eat at Post House, but I’ve heard it is really good! The shops next to it were fun as well and I loved their jewelry. Penelope grabbed a scoop of ice cream at the pharmacy.
After those shops, we headed over to Sullivan’s Island and walked to look at the beach, and then had reservations at The Obstinate Daughter. This was my favorite meal of the entire trip, and one you need to make a reservation for! I made our reservations two weeks in advance on Resy.
After dinner, we drove back to Charleston and parked by Rainbow Row (iconic) and walked around those streets (Broad, Tradd, Meeting etc.), which was fun to get a lay of the land. We also went to see the famous Pineapple Fountain over by the water, which was fun to walk over there as well!
Day 3
A recommendation I received a lot from people was to go see Kiawah Island. I was a little confused because most people said it was for members/residents only, but I drove over in the morning and told the gate person I was there to see The Sanctuar,y and they let me through. I know that you can also eat at Jasmine’s Porch, etc., and get through by dining there, and I wish we did that for breakfast! We just grabbed some acai bowls on our way out first thing in the morning.
The grounds were incredible and really neat to see and then we drove over to the public access beach which should be accessible here. It cost us $15 to park, but it was a fun beach to lay out at swim. These waves would be so perfect for babies and kids!
After we were done at the beach, we headed back into Charleston and ate at Lewis BBQ. This restaurant came very highly recommended, and we both LOVED it! Order the banana pudding to finish off your meal and thank me later. Close by is Hart Jewelry (if you want to make your own necklace!) and then go into the antique store next-door. So many treasures!
After our late lunch, we went back to the hotel and showered, and relaxed for a bit before heading back to walk the upper half of King Street and make our way over to dinner. We ate a Brasserie La Banque and thought it was such an enjoyable meal to end our trip with. We, of course, had to end our night with some Jeni’s Ice Cream as well! The Brambleberry is life.
Day 4
On our last day we woke up at headed over to Welton’s Tiny Bakeshop to grab some pastries and I wish I could’ve ordered one of everything! We tried the chocolate croissant and a breakfast biscuit sandwich and both were really delicious.
After breakfast, we drove down into the area South of Bread to walk and see all of the cute houses before heading back to the hotel to shower, change, and pack for our travel day back home.
On our way to the airport, we took a detour to Coastal Crust pizza and wow… if you are looking for delicious pizza while down there, go to Coastal Crust in Mount Pleasant!
I know we did not get around to doing everything but I thought it was such a wonderful trip and highly recommend Charleston for a vacation of any kind!
Things we didn’t get around to doing that people recommended are all in the spreadsheet but I do wish we went to Magnolia Plantations and Garden, Boone Plantation, and if I didn’t have my daughter with me the candle making classes at Candlefish looked really fun!
As far as tours go, a lot of people recommended the carriage rides (I for some reason can’t do these because I feel bad for the horses) and the Walking Sisters Tour.
And that is about it! I hope that helps you!
-Olivia
