I was hoping to be writing a post about my travels to Europe, but it just was not in the cards. I was supposed to be heading to London with my mom to visit my sister, but their intense quarantine rules for all Americans, including the vaccinated, had us pivot last minute. Ironically, just a few days before our trip, London waived their quarantine requirements for vaccinated travelers the day we were supposed to arrive. Just my luck!
Although staying in the US wasn’t the same, we planned a trip to make the best of it. Due to the crazy inflation on rental cars, hotels, and the like, we made it into a road trip. Now for those of you who know me well, know how much I do not enjoy a road trip. I will always choose to fly over drive. Looking back, I wish we would have flown, but I recognize that we wouldn’t have gotten the same experience out of the trip if we had. We hit 5 cities, drove through 7 states, and knocked a few things off the bucket list.
Day 1 (Chicago to Asheville)
For my own sanity, I put our longest driving day up first. We left nice and early at 6am on a Sunday. It really helped us avoid a lot of potential traffic leaving Illinois because summer = construction season on the highways. Our goal was to make it to Asheville before it got dark outside because those last few hours would be driving through the mountains. We made it to Louisville in great time and stopped for lunch at Cask Southern Kitchen. It was a perfect little spot to stop just off the highway. Those chicken tenders were delicious!
After grabbing lunch, it was a pretty smooth trip to Asheville. We experienced a little bit of traffic here and there, but made it to Asheville before sun down. We stayed at the Doubletree – Biltmore. Not only was it a great price, it was super convenient to visit the Biltmore Estate. One lesson we learned the hard way was that the dinner rush is real. There were a ton of chains and some local spots, but waits at most were an hour long for 2 people. We ended up just going to Friday’s since it was connected to our hotel and the shortest wait.
Day 2 (Asheville to Charleston)
We started our morning venturing to Biscuit Head. They have a couple of locations in the Asheville area. It was given as a recommendation from one of my co-workers and oh boy, it did not disappoint! I had the biscuit and a side and chose fried chicken as my side. It was so dang good. We also went on a Monday morning and the line was 10 people deep. It always good to find a spot beloved by the locals.
After grabbing breakfast, we headed over to The Biltmore Estate. This was absolutely one of the top things we did on our trip. We didn’t get to do the house tour due to it being sold out so now we have an excuse to go back! The Biltmore was so incredible that I wrote an entire blog post on it here.
After we visited The Biltmore, we began our drive to Charleston. South Carolina is one of the easiest states to drive through. It was only about 4 hours to get to Charleston. Upon arrival, we checked in to The Ryder Hotel. After a quick rest, we set out to find dinner. Even though it was a Monday night, Charleston was hopping. We had to go to a few different places before finding Henry’s. Henry’s is the oldest continuous bar in the state of South Carolina. You can hear live music at night.
Once dinner was done, we headed back to hotel before going on our ghost carriage tour with Old South Carriage Company. In Charleston, you will see carriage tours at all hours. While I was hoping that the tour would be more spooky, it did tell a few stories. If I were to do it all over again, I would do a daytime tour to soak in the history of Charleston.
Day 3 (Charleston)
Like every single day of our trip, it was a little dreary in the morning with a chance of rain. Our hotel had a complimentary bike rental for guests that was first come, first serve. My goal was to use those bikes! The first lesson learned was that riding a stationary bike in a fitness class doesn’t prepare you for riding a real bike. It had been years and it wasn’t as easy as “riding a bike” if you know what I mean. We took the bikes down Meeting St until we reached The Battery. It was a cloudy, dreary day that made the views a little less than usual, but it was my first taste of the ocean. It started to drizzle, but I wanted to make sure we made it to Rainbow Row. We got there just before a huge downpour to see the pastel row of homes. Maybe I expected more from all the hype, but this was a one and done type of event for me. On our way home, it began to rain cats and dogs as they say. We were completely soaked and need to relax after that adventure.
We didn’t have set lunch plans and followed the crowds. Every time we walked past Hyman’s, it was packed with lines out the door. It was another Charleston restaurant that has been around for hundreds of years and they play up that history. Each table has a name plate for famous people who have sat there. They are known for their version of shrimp and grits, but we went a different direction. It was a delicious meal and more importantly, pretty affordable.
We had a small window of no rain so we relaxed by the pool. That lasted about 30 mins before the rain came again. After such a busy morning, we hung out checking the radar constantly to see if there would be a break in the rain. The predicted break in the rain came and we were able to travel to Cypress Gardens, a place on the wish list if we could make it happen. Scenes from The Notebook were filmed here so you know it is an Instagram paradise and almost like escaping to another world. We got back just in time for our dinner at Hank’s Seafood. I love anything fancy so this brought that perfect combination of fancy and Southern. Do not sleep on those fried green tomatoes!
Day 4 (Charleston to Savannah)
After a relaxing morning, we checked out of our hotel and headed towards King St. King St. in Charleston is the main shopping strip. To get more details on our Charleston adventures, check them out here. We popped in and out of a few stores before heading over to Cru Café for an early lunch. No understatement when I said these salads were so flavorful. You can learn more about my favorite restaurants in Charleston here.
On our way out of town, we went to Magnolia Plantation. It was so beautiful, but also there was so much unexpected history. If you want to see all of the sights that they have to offer, I would go right when they open. There was so much to do that I wrote an entire blog post about the plantation here.
Once we finished, we made our way down to Savannah. It was a quick drive down and we got there about 6pm. We checked into our hotel The Cotton Sail. Savannah is unique in that the riverfront is so steep that one side of the hotel is about four stories before the entrance on the other side. Our room was on the fourth floor, yet was street side. After a full day, we grabbed dinner at PS Tavern. It felt like a college bar with decent food. Trivia was starting just as we left.
Day 5 (Savannah)
With another rainy day ahead of us, we set out to explore Savannah. I would split Savannah into areas, city center and then beyond. We started our day at the City Market. This open air market covers a pedestrian square. There are restaurants, shops, and even a museum for anyone to check out. It was a little dead first thing in the morning. Not sure if that was because of the weather or just people not getting their day started. We grabbed lunch at Vic’s on the River before hopping in the car. We drove to the Basilica of St. John the Baptist and took some photos outside and continued on to Forsyth Park. There were a few statues, but it is mostly just green space.
Then, we started our way out to Tybee Island, but on the way we stopped at Bonaventure Cemetery. The cemetery was pretty, but with the weather it made it hard to do much. I was excited to see Tybee Island since The Last Song was filmed there. Quite honestly, I was let down a little bit because I prefer a little more upscale island life. We spent a little bit of time on the beach before heading back to Savannah. We stopped at Leopold’s Ice Cream for a afternoon treat before relaxing at our hotel. We split an appetizer at Moon River Brewing before calling it a night since we were both excited to head to Hilton Head. If you want more detail about our Savannah experience, you can find that here.
Day 6 (Savannah to Hilton Head)
It was so easy to get up early and make our way to Hilton Head for the day. Driving in, so many memories came flooding back so of course we had to start with most memorable of them all, Sea Pines Resort. We headed to South Beach Marina to visit The Salty Dog Café. There was a wait so we ended up just visiting the store. Those iconic t-shirts you can find all over there Chicago area. After we headed over to Harbour Town. Harbour Town truly brought back all the memories from the Gregg Russell tree to the Christmas shop. After visiting almost every shop and taking pictures at all the landmarks, we grabbed lunch at Harbourside. Those drinks truly made it feel like vacation! Our last stop within Sea Pines was Turtle Lane. As a child, we would go there to feed the turtles and see the alligators. We only saw an alligator, but it was so nostalgic.
Rain was predicted all afternoon, but we had a short window of dry time. That made it the perfect time to do another nostalgic activity, mini golfing! We went to the Pirate’s Island Adventure Golf. Two hole in ones later, the rain began. We went to the outlet malls for a rainy day activity. They are now located off the island, but just right across the bridge. We popped into a few stores before heading back to our hotel. We ended with dinner at Hudson’s Seafood on the Docks. There was a long wait as they don’t take reservations, but it was worth every penny. You know that is the case when you forget to take photos of your main meal. The crab stuffed shrimp broiled was incredible! You can find more on Hilton Head here.
Day 7 (Hilton Head to Nashville)
We left Hilton Head early in the morning and made our way to Nashville. The ride overall was fairly smooth until we hit severe thunderstorms in the mountains of Tennessee. I consider our meals on the way home hitting all the chains we don’t have in Chicago. We grabbed lunch at Zaxby’s and dinner at Macaroni Grill. I really miss having a Macaroni Grill nearby. I took my mom on a drive by of Broadway and the state capital. Broadway was extra busy due to a NASCAR or IndyCar race in town. We stayed at the Hilton Suites Brentwood. I really recommend it if you are looking for somewhere outside of downtown.
Day 8 (Nashville to Chicago)
I couldn’t wait to get on the road to head home. After a full and rewarding trip, I was happy to be so close yet so far to home. The trip home was a fairly easy drive. We grabbed lunch at Fazoli’s and got home just in time to watch the White Sox game.
This trip certainly wasn’t what was planned, but I am happy I got to explore places new and old. I think I am now determined to visit Hilton Head yearly because it truly is my favorite vacation spot in the US.
Xoxo
Janelle
Leave a Reply