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Charleston, SC

Updated: Nov 12, 2022

September 2022 | Our itinerary Day 1: Saturday

Saturday morning we left Dallas around 10:30am and arrived in Charleston a little before 2pm. After hopping off the plane and picking up our rental car, we headed toward historic Charleston to check into our hotel which only took about 20 minutes.

Luckily once we arrived, our room was ready early so we were able to quickly set our bags down before heading to lunch. We ended up eating at Henry’s on the Market which was a super eclectic restaurant with a wide variety of food. Alec ended up getting the BBQ pulled pork sandwich while I had the blackened chicken pasta. The pasta was to die for and the BBQ sandwich was pretty good as well. Once we were done eating and paid our tab, we headed back to our room to relax and freshen up a bit before our dinner reservation. On our walk back however, we of course had to walk through The Market and do a little window shopping. The Market is basically like a farmer's market but is a permanent structure where local people can sell their goods everyday of the week, day or night.

After we were able to rest and recover from our travels, we started getting ready and made our way towards 5 Church for our dinner reservation. One thing we learned about Charleston very quickly was that on the weekends, you must have reservations! It is a very touristy and fairly small city so reservations (especially at the popular places) is a requirement. 5 Church is a beautiful, old church that got turned into a restaurant. It has gorgeous, tall ceilings with steeples and stained glass windows galore. Unfortunately we got seated in the side section so we didn’t get to sit in the main “church” area but it still offered a sophisticated ambiance feel. To drink Alec had the CU Stand Alone lager while I had the Ready Orgeat. To eat, we ended up sharing the ricotta gnocchi because neither of us were super hungry since we had such a late lunch.

Last stop for the evening was our reservation at Scotty Doesn’t Know. This was a super elegant and romantic experience that we couldn’t more highly recommend. After entering through a secret passageway (that you would never imagine lol) you are brought into a very dim, romantic atmosphere with candlelights and jazzy live music playing. We were sat in a back room across from this amazing couple who we chatted with the entire night. After sharing a bottle of red wine, lots of laughs, and unforgettable memories, we decided to stop by Doar Bros for a quick night cap. Another super romantic spot with the best vibes and service. Alec and I both ordered the Carajillo which were basically their take on espresso martinis and probably the best ones we have ever had. It’s nights like these where we can spend all day together but still come up with new stuff to talk about, that I know I married the love of my life and wow am I grateful! Once the clock struck midnight we knew it was time to head back to our hotel to rest up before the rest of our charming trip. Luckily we were just across the street from our hotel so we were able to easily walk back and hit the hay right away!


Day 2: Sunday

Sunday morning we decided to just grab coffee from our hotel lobby while we enjoyed our slow morning getting ready for our brunch reservation at Hall’s Chophouse. Most people go to Hall’s for a nice steakhouse dinner, but thanks to Alec’s uncle, we got to experience their Sunday gospel brunch instead. We heard the steakhouse is amazing as well but this was such a unique experience and something we had never done before. Everyday Sunday, they bring in a local gospel group which sings throughout your brunch dining experience. This is definitely more of a local thing and if you plan to go ahead a reservation is required and you should make it 2 months prior to the day you want to attend because they go so quick! Once we were seated, we ordered the fried green tomatoes to start (a very popular southern dish) which were pretty good. They had some seafood on top of it as well which wasn’t my cup of tea but the tomatoes were very good! Then to eat, Alec and I both ordered the french toast which was to die for but also massive, we absolutely should have split it + it came with bacon and we ordered a side of their potatoes because we couldn't resist. When I say you could have rolled us out of there, I’m not kidding. We literally ate so much our stomachs hurt afterwards but honestly it was so worth it. Some of the best brunch we’ve truly ever had + the staff and atmosphere were unmatched!

After brunch, we drove back to our hotel to relax for a bit and let our food settle because we were stuffed. Once we got in a quick cat nap, we then decided to gear up and head to Liberty Square to visit the South Carolina Aquarium and the Fort Sumter National Monument Museum. Alec and I really enjoy visiting aquariums and zoos in different cities when traveling and this one did not disappoint. It had a turtle conversation section along with a huge fish tank filled with unique sea creatures + tons of hands-on activities and attractions. Our favorite part was hands down sitting in front of the giant tank just watching all the large fish + sharks swim around.

After spending about an hour and a half at the aquarium, we decided to grab a drink at Island Cabana Bar before going back to our hotel to change for dinner. This was a cute dock area with a convenient store/restaurant located right on the water. Alec and I both picked a local drink to enjoy while sitting on the dock chatting the afternoon away.

Once we made it back to the hotel, we quickly changed, then walked over to King Street to catch our dinner reservation at O-Ku Sushi. This might have been our favorite meal in Charleston due to the incredible food and romantic vibe in the restaurant. We started with some spicy edamame of course before ordering our main courses. Alec is a big sushi fan so we try to always find a place that offers non-sushi items too because I am not a fan. After paroozing the menu for quite some time, he finally decided on the Potato and Surf-n-Turf rolls while I ordered the dumpling dim sum and fried rice. We both loved what we ordered and couldn’t get enough! After dinner we had originally planned to watch the sunset at Citrus Club Rooftop Bar which was highly recommended by tons of people! Unfortunately, I wasn’t able to make a reservation there beforehand (def a must if you plan to go on the weekend) so we just decided to walk up and put our name on the waitlist. Another bummer, but it had just started raining right as we were leaving dinner, so they had to move everyone who was outside on the rooftop inside, and it is mainly an outdoor rooftop patio. All that to say the waitlist line was insane so we decided to pivot and try Citrus Club another night. Instead we grabbed one last drink at Belmont before calling it an early night and catching some z’s before another amazing day exploring Charleston.


Day 3: Monday

Monday was probably one of our favorite days from the trip! Ever since living in California and moving back to Texas, we have been missing the beach like crazy. So we were super excited to be just a 30 minute drive to the beach + be on the east coast so the water would be way warmer. We started the day off by walking to Callie’s Hot Little Biscuits to grab some breakfast biscuits to help fuel us before heading to the beach.

Alec ordered the biscuit and sausage gravy and I got the sausage with jelly. Both were super tasty

but warning, this is a very touristy place so the line was pretty long. We went on a Monday around 9 am and waited for about 30 minutes (to place our order + get it). Additionally the interior was very small so once you place your order you have to wait outside and then basically are forced to take it to go. If we had known this we probably would have driven instead of walked but we were thinking it was more of a sit down place and it definitely was not. Once we made it about halfway back with our biscuits in tow, we decided to stop in a park and enjoy our breakfast on a bench while it was still warm. After we finished eating, we continued on our way back to the hotel to grab the rental car and drive to Sullivan’s island (which was about 30 minutes away).

We got to Sullivan’s Island around noon and were excited to find a parking spot and hit the waves! Luckily since we were there on a Monday, there were a ton of street parking spots as well as spots to set up camp on the beach. We parked near all of the restaurants on the main street because we were planning to grab an afternoon pick-me-up from that area later on in the day. During our beach day it was a little more overcast but we absolutely made the most of it! Honestly it was humid enough it still felt super hot so the water felt incredible to jump into and really helped us cool off. After spending 2 and a half hours soaking up the sun, playing in the sand, and splashing in the waves, we decided to walk up to the main street to grab a quick snack to tie us over before dinner. We ended up getting some frose and a sandwich to split from the Co-Op. They offer a variety of delicious sandwiches + frose for dine in or to go. Once we finished our sandwiches, we decided to get a frose to go and head back down to the beach to watch the sunset and take advantage of our short visit. After a quick little cat-nap while falling asleep to the waves crashing on the shore, we were ready to make our drive back to the downtown area to freshen up before dinner and drinks.

Since we weren’t able to get a table the night before at Citrus Club Rooftop Bar, we thought we’d try our luck on a Monday and hope for the best. Luckily when we showed up, around 7:15pm, we were able to get seated right away and watch the most beautiful sunset overlooking the entire city. While we enjoyed the gorgeous view, Alec enjoyed a X while I had the X and then of course we had to split the loaded fries which were incredible. The drinks were pretty good too but overall pretty price but you are truly paying for the view which we felt was super worth! Once the sun had officially set, we enjoyed an evening stroll back to our hotel and called it a night.


Day 4: Tuesday

Our original plan for Tuesday was to have a relaxing day on Kiawah Island enjoying the cute little town and doing plenty of shopping. However, we both loved our beach day at Sullivan’s Island, the day before that, we decided to change our plans and do a beach day at Kiawah Island instead. When we plan trips, we always like to have a general plan with reservations, knowing that we can change our minds at any time. We just always find it easier to have a general agenda to go off of and be able to change/cancel plans, instead of wasting time the day of trying to decide or waiting around to be sat at a restaurant because we didn’t make a reservation ahead of time. So Tuesday morning, we enjoyed some coffee from our hotel lobby while packing up our bags to head to a new beach.

Even though we loved Sullivan’s Island, we decided we wanted to try out the Kiawah Island beach to mix it up a bit and see as much as we could of Charleston. Before heading to the beach, we decided to enjoy some breakfast, Poogan’s Porch, which is a cute little restaurant located inside a historic building. Alec had their chicken and waffles while I ate their loaded mac and cheese.

Once we were done, we embarked on our 45-minute drive through the most gorgeous streets lined with willow trees galore, we made it to the Kiawah Beachwalker Park. We did have to pay $10 to park it, but this area offered a beautiful boardwalk with showers and bathrooms, unlike the beach area at Sullivan’s Island. Just like the day before, it was not crowded at all, granted it was a Tuesday afternoon, so most people were probably back at work. After spending 2 hours hopping in and out of the water and enjoying the extra vitamin D, we decided to pack up and head to Freshfields Village, which was a 5-minute drive to their downtown area filled with shops and restaurants.

Once we arrived, we quickly parked, and made our way to FortyEight Wine Bar. Luckily since we showed up around 4pm there was no wait, but our server did say they had a lot of reservations for that evening, so we had to give up our table by 5pm. Good thing for us is that wasn’t a problem at all as we had evening plans that we had to get back to the downtown area for. Once we were seated, our server explained how to wine bar worked. Basically you are given a card that you insert into the machine where you then decided what wine you’d like to try as well as how much (tasting, half glass, or full glass). At the end of your tasting experience, you then just give the server your card which tracks how much each tasting/glass was and pay. They have these stations set-up all around the restaurant for you to take your wine glass, serve yourself, while also read about eat wine you are sampling. We honestly had so much fun getting to taste all sorts of wines from all around the world while enjoying a tasty charcuterie board as well. Once the clock struck 5pm, we paid our tab, then walked around and did some window-shopping before grabbing dinner and heading back to historic downtown.

While we were at FortyEight Wine Bar, our waiter recommended we stop in Wild Olive which is known for being the best italian restaurant in the area. Unfortunately, that Tuesday they were closed for a staff appreciation event so we ended up stopping to grab some pizza from Tolli’s Trattoria. It was pretty good but nothing that knocked our socks off or anything, just a cute local pizza place. After dinner, we finished driving back to the hotel to rest up before our ghost tour. We did The Ghosts of Liberty which came recommended to us by a friend and did not disappoint. It was so fun getting to walk around the city at night (but be warned it was still very hot and humid lol) and learn all about the history of the city with some spooky twists as well.


Day 5: Wednesday

Wednesday morning we took our sweet time getting up and soaked in every last second of our hotel room stay before it was time to check out. Luckily Planter’s Inn had a super late checkout so we could have the room until noon. After grabbing a quick coffee from Bitty & Beau’s and a small breakfast snack from Peninsula Grill, we started backing up our bags to make the trek back home.

Of course before we left we had to walk through The Market one last time to grab our souvenirs before stopping at Bay Street Biergarten for lunch along the way to the airport. It was such a unique German inspired beer hall with tons of options on draft both local and not. Alec and I ended up splitting the wings + buffalo chicken dip with homemade chips. The wings were all right, a little on the dry side, but the dip was to die for! After paying our tab it was time to say goodbye to charming Charleston (+ the excessive humidity) and head back home!


What to wear

Charming Downtown Looks

Be sure to check out my LTKit page with more links + outfit inspo for you and your S/O!!


Where to stay

We absolutely loved staying at the Planter’s Inn during our visit to Charleston. It was in the perfect location, with the charmiest vibe, and sweetest staff. It is located in the heart of historic Charleston right on the corner of Market and Meeting Street with King Street being only one block away.

Additionally, there is a parlor that offers complimentary coffee + tea every morning as well as fresh, warm cookies every night. Attached to the historic hotel is an enchanting restaurant, Peninsula Grill, which is known for being the most romantic restaurant in the city.

The hotel offers many different types and styles of rooms all varying in price. We stayed in the Charleston King room which was the perfect amount of space for the 2 of us. It had a beautiful, 4 post king bed with a large closet and huge walk in bathroom. Plenty of space for us to sprawl out for our 5 day trip and not feel cramped. We were on the first floor with a window facing Market Street but luckily the windows were double paned so we couldn’t hear anything outside at all which was super nice.

*One of the main reasons we chose to stay at Planter's Inn was due to the price and location. It truly was in the center of all the action, close to all of the main streets, and just as nice looking as the rest of the hotels for a fraction of the price.

Other hotels


How to get around

So depending on where exactly you stay and what all you want to see/do you don't necessarily need to rent a car. Since we stayed at Planter's Inn which was a short walk away from all of the main streets (Meeting, Market, and King) we totally could have gone without a car. However, we wanted to see more of the city so we are more than happy with our decision to rent one for our trip! Our best recommendation would be, if you plan to just stay in the historic district area, don't rent a car. The airport is only 20 minutes from the downtown area so you could easily take an Uber then just walk the city + parking is limited and therefore more on the expensive side.

However, if you are planning to go to Kiawah, Sullivan's Island, Isles of Palm, the aquarium, or just drive the streets of the beautiful city, then a rental car is a must! We rented our car through Expedia and only paid $90 per day. Granted we did have to pay for parking at our hotel as well which was X a day but it was valet so anytime we needed the car we just had to call the front desk and they brought it to the front of the hotel in no time. And if you do rent a car just be sure to read the parking signs carefully, as they can be tricky. But on Sundays, on King Street, the parking is free but goes quick. So get there early if you want to get a spot.

Another thing about "how to get around" the city is super walkable but just be prepared, it is super humid (almost year round) so if you are walking you are likely sweating. Just something to keep in mind incase you aren't a fan of profusely sweating in nice clothes like us lol. Additionally, we didn't ever end up doing it but you can also rent bikes (most hotels have them for free too) and ride through the city to avoid walking if that's your thing.


Where to eat

Coffee + Breakfast






Acme Seafood (Isle of Palms)

Coda Del Pesce (Isle of Palms)



Drinks & Dancing




What to do

In Charleston, SC, Tour Pass is a great option if you are looking to do a lot of tours, excursions, and site seeing at a discounted price. Be sure to use our affiliate link for bundling discounts when planning your trip to this cute and quaint little town! More details below regarding what all is included in your Tour Pass ticket, along with pricing as well, happy planning!

⁃ Palmetto Carriage Tour

⁃ Boone hall

⁃ Harbor tour

⁃ Old slave mart museum

⁃ Charles Towne Landing

⁃ Deep water vineyards

⁃ Confederate museum

⁃ Aiken-Rhett House

⁃ Old Exchange & Provost Dungeon

⁃ Charleston Museum

Beaufort (for the day)

Ghost Tour Options (all tours are about 90 minutes long)

Jailhouse Tour (temporarily closed)


What to save

If you are planning to travel to charleston during the fall, you should expect to spend anywhere from $2,000-3,500 (travel & stay included).

Flights: $800

Hotel: $350/night (booked through Hotwire)

Food, Drinks, & Activities: $250/day

Rental: $90/day (booked through Expedia)


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