Travel Guide: 76 hours in Charleston, SC

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Yellow Gingham Style - Travel Guide: 36 hours in Charleston, SC // Matching Yellow Gingham Set - Travel Guide: 36 hours in Charleston, SC //

Top: (similar here) | Skirt: (similar here) | Choker: Natalie B | Sneakers: (similar here)

The time to head South is now. With its cobblestone walks, historic homes, and famous spots for delicious country fares, Charleston has all the charms of a city we’ll never tire of. And I’m so pleased to put together this comprehensive travel guide for those of you who are ready for serious southern allure and cuisine.

Travel tips: A few things to keep in mind if you’re ready for Charleston, South Carolina. Most places are accessible by foot, this means no need to rent a car or worry about public transportation. With a bike or a quick Uber tap, you can be onto your next spot in a matter of minutes. I was able to get where I needed to go with ease by using Uber most of the time and I wasn’t disappointed at the efficiency of the service, either.

Packing tips: Since this is the South, temperatures are quite hot and as summer approaches, they will get even steamier. The weather is sunny most of the time which means shades and plenty of sunscreens. It also means a hat, breezy tops, dresses, sneakers, and tons of bug repellent (I prefer these wipes or the bracelets for the kids) because there is no shortage of mosquitos. Think laid-back fashion with light, breathable fabrics, and minimal jewelry.

Day One

Red Gingham Ruffle Dress - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.com86 Cannon B&B - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.com86 Canon B&B Areas - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.comCharleston Pink Door and Red Gingham - Travel Guide: 36 hours in Charleston, SC //

Dress: Fame and Partner | Shoes: (similar here) | Earrings: Kendra Scott | Necklace: Natalie B

After a short flight from New York, I arrived in Charleston. It was my first time visiting so I wasn’t too familiar with the airport so I relied on using Uber at the Charleston Airport to get to my B&B. I stayed at 86 Cannon and did my check-in in the afternoon. I chose to stay here because I wanted to get a true taste of Charleston’s hospitality by staying in one of the many B&Bs. Not only do these serve you breakfast, but many are located in historic homes which add an element of magic. This particular one is a remodeled home from the 1800s.

The neighborhood is off the beaten path, which made my stay feel authentic. I could literally feel how it might be to live here. While the neighborhood is tucked away, it’s rumored to be an up-and-coming area. What I found was a great art/food/shopping scene that mostly only locals frequent. Nothing is better than chatting with locals to understand the town, culture, and history. The B&B offers simple breakfast of coffee and juice, almond croissants, yogurt, and cereals. Not the typical Southern down home breakfast, but it serves the purpose and saves time in the morning. Between 5-6 pm, they offer wine and cheese tasting. It was a nice touch. The mini bar is complimentary, wine, however, is not.

Rating: 4/5
Price:  $$
Tips: They provide bikes! This is a wonderful way to check out the neighborhood and beyond. It gave us a better idea where to go the next day as well.
Alternative (where you will find me on my next trip): Zero George Hotel

Charleston Homes at Night - Travel Guide: 36 hours in Charleston, SC //

We dined at Husk, a restaurant famous for southern-style cuisine. However, we weren’t very pleased with our food. The chicken skin appetizer was delish but quite greasy, the meat board was salty, both corn bread and breaded catfish were very dry as you might have seen via my Insta-stories. The chicken lacked flavor. However, their menu changes daily, so everyone’s experience will be very different. Perhaps we came on a bad day?

Rating: 3/5
Price:  $$$
Tips: In order to get a spot at Husk, you need to book in advance. They do take walk-ins if you don’t mind waiting for a long time and then eating late. This is exactly what we did. We stopped by early to leave our name on the list, then went off to explore the town a bit. If you’re a whiskey fan, they have a Husk bar next door where you can waste the minutes away while indulging in a Southern classic and feeling super relaxed.

Day Two

Floral Embroidered Stripe Blouse and Shorts - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.comCharleston Charming Houses - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.comRainbow Row Charleston - Travel Guide: 36 hours in Charleston, SC //

Top: (similar here) | Shorts: (similar here) | Shoes: (similar here) | Sunglasses: Miu Miu

Rainbow Row is only a 10 minute ride from our B&B making it super easy with an uberX ride. Located just south of Broad Street. It offers a cheerful pastel-painted neighborhood, the most photographed part of Charleston.

Next, we went to Waterfront Battery where we saw the famous pineapple fountain. Here we could sit back and really get into the Southern way of life. Later we made our way to Tradd Street which is home base for the famous Charleston charm. Streets were lined with flickering copper carriage lanterns and we felt like we stepped through a time portal.

Southern Fried Food - Travel Guide: 36 hours in Charleston, SC //

For lunch, we made our way to Leon’s Oyster Shop, another place known for Southern-style cuisine. We ordered a chicken sandwich and a fish platter and enjoyed the rustic feel of the town.

Rating: 4/5
Price: $$

Although there was a huge storm in the afternoon, it didn’t really kill our spirit much. We took the opportunity to squeeze in a nap in our charming B&B and was rest assured that we could rely on the Uber service in Charleston to venture out to dinner. For dinner, we slipped into The Ordinary. They have plenty of seafood cuisine to satisfy any seafood lover. Once a bank from the 1920s, it now houses an upscale seafood restaurant with vaulted ceilings, expansive windows, and a well-stocked bar. We ordered the seafood tower, a smoked oyster appetizer, and a roasted red snapper served whole and cold lobster rolls.

Rating: 5/5
Price: $$$
Tips: They have daily specials, so take advantage of the offers.  Also love the $1.50 oysters during oyster happy hours Tues – Fri 5:00-6:30PM. Well worth it!

Day Three

Boone's Plantation - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.comBoone's Plantation - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.comAll White in Boone's Plantation - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.comSouthern Greenery - Travel Guide: 36 hours in Charleston, SC //

We started our day at Black Tap Coffee. A perfect stop for a cold brew or lavender latte with almond milk. A latte lover’s dream for minimal fees. Don’t let this place pass you by.

Rating: 5/5
Price: $

Boone Hall Plantation is one of the country’s oldest working plantations and most photographed. Although it was about a 25 minute Uber ride away, it was well-worth the trip for the history lessons when in Charleston. The fact that we stood on a piece of history and learned more about slavery really helped us understand the South more. It is a must-see for the architecture, but also the lessons.   

The Americano - Travel Guide: 36 hours in Charleston, SC // Getting around with Uber in the Americano - Travel Guide: 36 hours in Charleston, SC //

Top: (similar here) | Skirt: Planet Blue | Shoes: Free People | Earrings: Free People

The Americano was only 15 minute Uber ride from the Plantation, plus it was on the way to the beach.  A nice place to stop to grab a quick drink and to catch a breeze. However, the brightly colored space was perhaps the main attraction.

The Obstinate Daughter - Travel Guide: 36 hours in Charleston, SC // NotJessFashion.comSouthern Comfort Food - Travel Guide: 36 hours in Charleston, SC //

The Obstinate Daughter was the lunch spot that offers rustic Italian cooking and Lowcountry seafood. Our order included a crab salad, Old Danger pizza (don’t miss out!), and smoked local fish. Bonus, The Obstinate Daughter is so Instagram-worthy,  the casual beachy vibe includes rope lighting, gray wood, and blue tones.

Rating: 5/5
Price: $$

Sullivan's Island Stroll - Travel Guide: 36 hours in Charleston, SC //

For an after lunch stroll, Sullivan’s Island was ideal. A walk on the beach was the perfect plan. And we got there right before the storm hit. Sullivan’s Island very quiet, almost secluded, and it should be noted that there are no lifeguards on duty. Just 20 mins away from the city, it has lots of delightful restaurants and shops to keep the whole family happy. It was a busy day, but Uber made it possible to see all these places in Charleston in the same day without any hassle.

We wanted to stay in for dinner, so we got David’s Carry-Out. This is soul food at its best.  It’s recommended by a lot of my followers and is a local’s favorite. Good food that won’t break the bank? Yes, please. We got chicken wings, a seafood platter, oxtails, and pork chops. It was a mountain of food, to say the least!  A hidden gem that delivers charm and cuisine.

Rating: 5/5
Price: $

Day Four

Charleston Charming Houses - Travel Guide: 36 hours in Charleston, SC //

Hampton Park isn’t on the must-see lists of things to do in Charleston, but we went there for a quick morning stroll. It was peaceful enough and gave us decent contact with green spaces.

The Park Cafe - Travel Guide: 36 hours in Charleston, SC //

For lunch, it was The Park Café, located right next to the Hampton Park. Perhaps after 3 days of Southern food, we wanted to take a break. Hubby and I both got The Park Lettuces with chicken and shrimp, totally scrumptious. Also, do try their Cold Brew Creations if you’ve got a sweet tooth. I had Eastwood –coconut and whipped Nutella, better than I expected, so, so good.

Rating: 5/5
Price: $$

BONUS: Although it rained a lot during our stay, thanks to Uber, we got to where we wanted to go with ease and in minimal time. Here are a few places that were on our list that we were hoping to see, but we didn’t get to visit. But now it gives us a reason to go back!

– Charleston City Market
– Magnolia Plantation & Gardens
– Candle Making Class at Candlefish
– Carriage tour of downtown Charleston
– Hominy Grill for a hearty breakfast

Hope you guys enjoyed my Charleston guide. Have you been to or are you headed to Charleston? What were you favorite spots or are planning to see? Please share them with me below.

*Thank you Uber for sponsoring the post!

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  • I have always wanted to visited Charleston! Love all your outfits here!


    Tamara –

  • Wow, your outfits are super amazing! Love your stunning photos!

    – Cielo
    Mermaid in Heels

  • Gosh, your pictures are just beautiful and I love that red/white dress on you. I must admit I had a very different experience when I visited some ten years ago – the city I’m from is a melting pot of cultures – back then the racial divide was noticeable & quite shocking. It’s refreshing to read more about your trip and get an update on it now! I’d love to visit the Boone Hall Plantation to learn more about its history, even though I’m sure it was pretty heart wrenching.

    • I guess that warrants a return visit. You will love it!

  • What a fabulous post! I adore that sweet city and you look so elegant and chic in everything you wear. Love the gingham in yellow, and the breezy two piece in off white. Fabulous!
    xx, Elle

    • Glad to know you loved Charleston too! Where did you go to?

  • Loving all the photos from your Charleston trip! Gingham looks amazing on you!!

    xo, Olivia

    • Thanks Olivia. Love it too!!

  • The Gold Lipstick

    Absolutely love it!

    Mireia from TGL

  • This is probably the most complete travel guide of Charleston I’ve seen, Jess! It looks like a lovely city, I’d love to visit it come day 🙂

    • You should Cristina – you will love it!

  • My goodness, what absolutely breathtaking photos! I’ve been to Charleston MANY times, but not in the past few years. I’d love to go back this Autumn and try a few of the places you recommend, because most of them are new to me. xx

    • Yes definitely worth going back to!

  • Your outfits are beautiful and I love these photos!


  • fatou diaw

    I love all the outfits! so cute!

    • Thank you. Glad you liked them!

  • Briana Trevino

    I just spent about 2 hours there for a layover! Doubt it counts but I plan on going back to really visit!


    • Well, definitely not enough. You need to visit again!

  • Steph K

    I just love Charleston!! Isn’t is Charming?! It’s one of my favorite cities to visit.
    Love all your outfits – especially the gingham looks!

    xo, Steph

    • Glad you feel the same way Steph. I love it!

  • Wow Charleston looks amazing! I honestly haven’t had a strong desire to visit the South, but after seeing this post I’ve changed my mind. The city looks so colorful and quaint!

    • Yes, so many beautiful cities in the South.

  • Nina

    Loved all your outfits. and the place you stayed in . I would love to visit Charleston one day. Your photos made me want to go there sometime soon.

    Nina’s Style Blog

    • Sorry to inspire your wanderlust, but it was too good not to share.

  • Mireia Estefano

    Cool places!! Love the photos a lot =)

  • WOW this is beautiful! I can’t wait to book a trip here!

  • I wish I could do a travel post like this one.. love all the photos because of how awesome they are, not just because of the outfits… you embody everything a fashion blogger should be. LOVE it Jess!!

    Jessica || Cubicle Chic

  • Kay Nguyen

    Everything is so beautiful! I have never been to Charleston before but it’s on my travel list! Love your blog <3

    • Ah, hope you can tick it off your bucket list!!

  • Christine

    Wow, I would never even think to visit Charleston, but all these photos of the charming homes and amazing restaurants make me want to book a trip there right now! I haven’t discovered all the quaint cities like this in the US, rather going to large cities, but this sounds like such a lovely vacation, even with the kids. I love all the honest food recs and the fact that you can get around easily by walking, biking or a quick Uber ride. All of your outfits are gorgeous and love the vacay style. Thanks for sharing so much about the charm and hospitality of South Carolina. xoxo, Christine

    • I highly recommend it. It’s popular for a reason!

  • Ahhhh I love Charleston. I have only been once and it was some time ago. This makes me ready to book a trip ASAP.

    Amy Ann
    Straight A Style

    • Yes Amy, I couldn’t recommend it enough. So much beauty and charm!

  • Glad to be of help Jill!!

  • It is charming indeed. Loved it!

  • Very thorough post, so many gorgeous photos! I especially love your yellow gingham outfit. I don’t see many people go the yellow route with gingham, making your’s even more special.

  • Charleston is SUCH a cute town! I love all the pastel buildings- great guide, lady!

    Le Stylo Rouge

  • Ophelia Tang

    Sounds like fun! I’m also loving all your outfits. The different color gingham prints really suit you too! I love it! <3

    XOXO //
    SINCERELY OPHELIA | NYC Petite Fashion Blogger

  • Mihaailo Pejnović

    I am obsessed with your daily looks!

  • This should be no surprise to you. But you are at it again! Another stunning post featuring beautiful and stylish clothing!

    Dimito Michiyo

  • Just a great post with very useful tips. Your looks were incredible and the most I liked your dress from day 1.

  • Love the gingham and the flowy whites, lovely post!

    • Those are some of my faves, Sophie!

  • Mes Voyages à Paris

    Amazing pictures!! I would like to be there!!
    Mónica Sors

  • Rach

    I’ve been wanting to go to Charleston! Your photos looks amazing and I’m loving every outfit!

    • Oh you need to Rach! Thank you for dropping by!

  • I love Charleston so much! Thanks for all these great pics and I adore all your summer looks.

    • Thanks Kathrine. Glad you liked these looks!

  • Charleston looks amazing!


    style frontier

    • It is!! Thanks for dropping by!

  • Loving all your looks, especially the yellow! I still haven’t been to Charleston, and need to just get in the car and drive there since it’s so close <3

    Green Fashionista

    • This is your reminder to! Thanks Kate!

  • I’ve always wanted to visit Charleston. Love these photos!

    • You need to visit Sam. It’s amazing there!

  • Hi Jessy, your photos are so beautiful. I would love to visit Charleston on day.


    • Thanks Miri! You will love it for sure!

  • Jessi Afshin

    Wow, looks like you had a fun trip! Your outfits and photos are perfection 🙂


    • Thanks Jessi. It was fun indeed!

  • Neha 14wow

    U look so beautiful babe…and I cant keep my eyes off your pics…each n every outfit is ust wow!! And seems like you had a great trip…!! I like Charleston ! Kisses and Hugs, Neha

  • Charleston has been on my bucket list for so long now, I hope I get there next year! Thanks for the awesome recommendations Jess!

    I hope you’re having a lovely week,

    • Good luck. I hope you’re able to!

  • Mackenzie

    Jess, this was an awesome post! I live in Hilton Head Island, SC, so I go to Charleston at least once a month. If you go back, please eat at 82 Queens. It’s the best place to eat an amazing brunch, and the courtyard is charming. It’s literally two doors down from Husk! Also, Folly Beach is an amazing place to visit. It’s 11 miles from downtown Charleston, and there’s an amazing restaurant called Taco Boy that serves up mainly tacos. It’s a cute spot, very cheap, and very good. There’s even a Taco that is a combo of fried chicken and Sriracha.

    • Great tips Mackenzie! I will definitely make a note of your recommendations for when I do go back!!

  • As always great guide! 😉

  • Your photos are SO beautiful! What a charming town. Looks like you had a lovely visit.
    Charleston is definitely on my list on places to visit. Love your outfits too! That gingham dress is perfect for summer

    • I did. You should definitely visit – you’ll love it!

  • Love your outfit<3

    It looks so fashionable! xx

  • CoRina Culeva

    Love these pictures! And I fell in love with the red dress!

    xo Corina

  • Tina – Styleappetite

    These pictures are amazing – and I looove that red gingham dress on you ♥ What a fantastic look! 🙂
    have a great weekend love,
    xxx – Tina

  • That gingham dress is so so adorable!!

  • STUNNING photos!! I love all of your outfits especially the red gingham and that white dress…ah so pretty. From this post, I definitely want to travel to SC asap!!! xo

    Trendy & Tidy

  • Louis Dupond

    Great outfits and location … thanks for sharing!

  • Kim

    Your photos are absolutely GORGEOUS! I’m getting so much wanderlust from them. Hope to road trip down to South Carolina someday! My fiancé has some family there!

    Simply Lovebirds

  • Dhwani Parikh

    Its hard to say which ootd is the best, but must say You have put a great post esp bz Iv always wanted to go to Charleston and this post helps! Love the red gingham dress and those earrings ❤️

    xo, Dhwani

  • Charleston looks so cute, makes me want to go there! Your outfits were so lovely and I love those statement earrings <33