Charleston Travel Guide Fall 2021

I’ve been to Charleston, South Carolina a few times now and was dying to go back and visit during the fall time. I love just about everything the city has to offer and wanted to see it sometime other than the summer to get a better feel for it. After this trip, it’s safe to say it’s definitely in the running for a potential post-grad move!

Unfortuantely, my trip was just three days this time around. I had enough time to partner with an Airbnb, do a little exploring, eat a few hefty meals, and shoot some content with my Instagram friends. It was the best weekend getaway and to be honest—during the fall I don’t feel like you need too many more days anyways.

I will say, I was shocked to see the city as busy as it was. there were definitely more people in November than in June/July when I’ve visited. However, it was mostly older people participating in the historical tours + carriage rides mixed with the college kids in town for the school year. Nonetheless, I had a fantastic time and am always infatuated with their hospitality.

Where To Stay 

I’ve been to Charleston twice before and both times I stayed at my sweet friend Molly’s house. She is lucky enough to live just fifteen minutes from Downtown and she’s been the best hostess over the years. This time around I stayed in an Airbnb both nights and had a wonderful experience at both properties.

Captains Quarters (click here to book)

I’ve explored several areas around Charleston but haven’t spent too much time by the beach. I wanted to switch things up and booked a quaint condo in Folly Beach for the night. Folly is an adorable beach town with several restaurants, touristy shops, and the ocean just a couple of blocks away. It’s so convenient having everything within walking distance—especially if this were beach time.

Although small, Captains Quarters was just what we needed for a solo night stay with a queen bed and a newly renovated bathroom. The space was adorable and absolutely spotless! It did have a fully stocked kitchen and space to park as well.

The Four Winds Inn (click to book)

The second night I stayed at The Four Winds Inn. This was an adorable Airbnb nestled in a safe neighborhood amidst James Island. Although this space is attached to the host’s home, you have lots of privacy and everything you could need. Similar to our last place, this one was super clean and very inviting.

The Four Winds Inn sleeps four with two bedrooms, each equipped with a queen bed, a TV, and cute decor.

Through the first door, you have a fully stocked kitchen and dining area that gives way to a spacious living room with lots of character. These velvet couches are my favorite touch.

The bathroom is Old Hollywood inspired with moody lighting, fun wallpaper, and everything you could want-including cozy robes. I couldn’t have asked for a better stay here. A huge thank you to the hosts for being so accommodating and for the fantastic stay. I’ll definitely be back!

Where To Eat

I’m not going to lie—the food is one of my favorite parts of Charleston. I swear every time I come here I leave with pants that fit a little tighter because everything is just that good. I was fortunate enough to partner with a few restaurants this trip—going back to a few old favorites and discovering some new ones as well!

Eli’s Table 

menu // directions

I’ve had a few people recommend Eli’s Table to me over the years so we popped in for a late lunch. they serve breakfast all day so naturally, I had to get it. I got the scrambled eggs, bacon, avocado, and cheese on a biscuit and man was it the right choice. Nothing beats a Charleston biscuit + the potatoes were fantastic.

I will say, the atmosphere of this place is nothing special, especially compared to other restaurants in the area but the food and service were great!

Wiki Wiki Sandbar 

menu // directions

Wiki Wiki is the cutest restaurant in Folly Beach! I went the last time I was in Charleston and loved the vibe so much I just had to stop back in. Whether you’re inside or outside the atmosphere is immaculate with cool sea glass and beach decor everywhere. We sat here for hours after eating our meal just chatting and laughing. I can’t describe it but the vibes are just so good.

We started with the calamari and it was delicious. The mango salsa adds a sweet element that’s so good! I got the crab cake sandwich as my main course and there was tons of crab in it. The mix of avocado, bacon and spicy mayo was delicious and I always ask for the grilled pineapple on the side. If you’re of age, their drink menu looks fantastic as well. Although I got the virgin strawberry daiquiri and it didn’t disappoint either.

Taco Boy Downtown (menu)

menu // directions

Taco Boy is hands down my favorite restaurant in Charleston. I’ve always loved Mexican good but something about this place is just unmatched. There are three locations and we stopped into the Downtown one. Of course, we had to start with the appetizer trio—their guac and queso are to die for. We also got the delicious queso fries.

I got two tacos: the chicken, back, ranch, and the surf & turf. The surf & turf was definitely my favorite with tons of flavor + lots of shrimp. You have to get the street corn when you come here—it’s without a doubt the best I’ve had. I washed it all down with a basket of churros. I cannot recommend this place enough. Everything (and I mean everything) on the menu is so good; I can’t imagine coming to Charleston and not stopping in here.

Bay Street Biergarten 

menu // directions

Molly took us to Bay Street for more of a “locals” spot and it didn’t disappoint either! They sat us outside and the twinkly lights + incredible country music playlist made for the perfect night. I got their double cheeseburger. It was good however, I forgot to ask for it medium so it was a little overdone for my liking. Their tater tots on the other hand were incredible! I highly recommend.

They also have live music here on certain days of the week. Definitely check out their Instagram beforehand. I’m so sad we missed out!

Poe’s Tavern 

menu // directions

A few of Devon’s subscribers recommended this cute restaurant down by Sullivan’s Island so we popped in for lunch. Everything that was being delivered around us looked delicious that I could hardly choose what to get. I ended up with the shrimp + chorizo quesadilla and it was bomb. The toppings made all the difference! I definitely recommend getting a side with this as I was still hungry after eating.

The Beard Cat

menu // directions

The plus side to being hungry after eating lunch was that I had room for a sweet treat. We stopped in the Beard Cat, a local favorite for some gelato and man was it good! I got their strawberry banana which tasted more like the base of an acai bowl. I did get it in a waffle cone for the sake of a photo and would def recommend just sticking with a cup as the gelato seeps through the cone causing a mess! 10/10 on flavors though.

What To Wear 

I’m from Maryland but have lived in Ohio for the last few years and let me tell you, November in Charleston is an absolute dream. I cannot imagine how much better my mental health would be if it were seventy and sunny this late into the year, lol. If you are coming from the North/Midwest you’re in for quite the treat.

Because of this, I wasn’t quite sure what to pack. I had a few dresses and sandals but also brought a few sweaters and jeans outfits. To be honest, I wore them all. The entire weekend was that temperature where you could really wear either outfit and still be comfortable. I recommend having light layers on hand as it did get a little brisk in the mornings/evenings.

I find that just about anything goes here—however, Charleston is definitely a place rooted in class so perhaps leave your hoochie-mama tops home this trip.

I put together an outfit guide with thirteen different outfit ideas to give you some inspiration. I’ve also gone ahead and linked everything + shared photo locations so you can recreate these looks in this blog post.

What To Do 

Honestly, my trip was so short this time around that I didn’t have the chance to “do” all that much. My weekend was more about exploring the little side streets of Charleston, capturing content, and spending time with my girls!

However, I’ve been to Charleston a few times now and have definitely done my fair share of touristy stuff. I recommend checking out this post for my full scoop on the most popular attractions: Rainbow Row, The Pineapple Fountain, The Battery, Shems Creek, and more.

Stop In Dress Up Along King Street 

No trip to Charleston is complete without a trip to King Street. The shopping here is too good with a mix of local favorites and high-end designers. I stopped in Dress Up this time and got to choose a few pieces as part of an Instagram collaboration. They have the best mix of trendy items, timeless basics, and touristy Charleston tees. I grabbed this blue sweatshirt and am obsessed with it.

The best part is, you can shop Dress Up online too! Use my code MCKENZIE15 in store or online to get an additional 15% off! Oh, and did I mention that the second Sunday of every month they block off King Street so you can walk in the streets. It’s definitely busier but it’s so nice not feeling so crowded!

Catch The Sunset on Folley 

Nothing beats a sunset on Folley Beach. We walked down to the water and caught the most amazing view right before the sun went down. I was shocked at how many couples/families were out walking along the water. Definitely the perfect evening activity. I felt the water just for shit and gigs and man was it cold!

Explore The Historical Homes 

My main goal for this trip was to shoot some content with new pieces. I’ve been to a lot of the main spots in years past and wanted to find some cute new locations to take photos. We bopped around the residential side streets and found the cutest homes. Several of them have historical significance too which is fun to learn about if you’re a history buff! Don’t worry—if you’re just looking for a cute colored house (like me), you’ll find that too.

Visit Sullivans Island 

I went to Sullivans Island to sit on the beach my first trip to Charleston but it’s been years since I went back. Devon and I decided to pop down for lunch + to walk around and it didn’t disappoint. Despite it being the off-season, this quaint beach town was still very much alive. However, it wasn’t overcrowded—just rooted in southern charm and hospitality. I loved getting to see it during this time of year.

Almost every restaurant long this strip is still open during the offseason so it’s worth driving down for lunch, an ice cream cone, and a quick peek into the surf shops. Plus the water is worth the view!

Walk Through College of Charleston

I walk through College of Charleston every time I come to visit—partly because it’s so beautiful and partly because it’s free parking on the weekends at the library right next door, lol. It was really cool getting to see it during the school year. There were students everywhere, friend groups taking photos, and people sitting at tables studying. As much as I love Kent, it definitely makes me wonder what my college experience would have been like if I had chosen to go to college somewhere else.

It really is the prettiest campus and definitely worth the walk-through.

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Well, that’s a wrap for this mini Charleston trip! I can’t express how lucky I feel to be doing what I love + seeing cool places while doing so. I cannot thank you enough for joining my corner. Up next… FLORIDA 😍 stay tuned!

With love, McKenz

Latest Post: What To Wear In Charleston Fall 2021
Related Post: Charleston Travel Guide Summer 2021
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