March 7

Ultimate 48 Hour Charleston Itinerary

Our FULL Charleston Travel Guide is finally live! Be sure to check it out over here (right under the ‘Travel’ section in the nav bar) and browse through all of the content- restaurants, activities and places to stay. Each one is broken up into categories. Best food & drink has coffee shops, breakfast, lunch, cocktails, dinner and sweet treats. Things to do in Charleston has outdoor activities, tours, indoor activities, shops to visit and day trips. Hotels are broken up into small & intimate vs larger hotel options. Additionally, we’ve linked to more Charleston posts that we’ve done over the past few months of living here and will continue to add as we explore and try more things!


Heading somewhere new can always be a bit overwhelming, especially if you’re limited on time. We’ve taken some of our favorite bits from the guide, narrowed it down and made this ultimate 48 hour Charleston Itinerary. It has you covered for every meal (because let’s be real, most of us plan our weekend getaways around the best restaurants!) and things to do, along with a recommendation for a new favorite Charleston gem to stay at. And if you’re here for a few additional days or recommendations, just check our full guide for more!


Charleston Itinerary where to stay 86 cannon
Charleston Itinerary where to stay 86 cannon



86 Cannon is a brand-new, beautiful Charleston Inn that’s actually a restored home from the 1860s. It’s an intimate space, with only five rooms, so it’ll feel like your own private escape in the city. You may have arrived just before check-in, but don’t fret! After traveling to Charleston, you are probably hungry for a bite to eat. A couple blocks down from 86 Cannon, Xiao Bao Biscuit awaits your arrival. This is one of our favorite restaurants downtown because of its unique menu options that leave you more than satisfied. Try up to four of their dishes if you are splitting between two, or more if you have a larger party. We recommend their Cabbage pancake and suggest you order all of the toppings for it.


Charleston Itinerary where to eat Xiao Bao Biscuit


After lunch, there are a couple of little shops you can pop into before heading back to the hotel. Take the time to check out these shops in the lovely Cannonborough/ Elliotborough neighborhood that you will be staying in for the weekend. Just down the street, there is an adorable little card shop, Mac + Murphy, where you’ll find all of the Charleston postcards you can imagine. A couple doors down from Mac + Murphy is Sugar Bakeshop. There is nothing better to jump-start your trip than a touch of sugar from their wonderful cupcakes.


Charleston Itinerary where to shop mac & murphy
Charleston Itinerary delicious treats from sugar bakeshop

Charleston Itinerary where to shop mac & murphy

Charleston Itinerary where to stay 86 cannon


After you get back to 86 Cannon and explore the beautiful house you will dwell in for the next few days, you might want to refresh and relax before jumping into all the activities Charleston has to offer. Take a break on 86 Cannon’s beautiful porch and gear up for your night ahead!


Charleston Itinerary where to have cocktails Darling oyster bar
Charleston Itinerary where to eat darling oyster bar


The Darling Oyster Bar is the perfect location for cocktails. We love sitting at the Raw Bar and drinking their Paloma cocktails or a glass of Rosé. The Darling has a wonderful atmosphere and the appetizers are delicious. We recommend the shrimp and their oysters, of course. After you’ve enjoyed your time at The Darling Oyster Bar, get ready for a slightly more romantic dinner setting at Chez Nous. Chez Nous is a French boutique restaurant close to 86 Cannon, and they are all about the details. You will swoon over the handwritten menu, fresh bread, and quaint interior.  After your delicious dinner, enjoy the night in one of 86 Cannon’s gathering areas: out on the piazza or in The Salon.


Charleston Itinerary where to eat darling oyster bar

Charleston Itinerary where to eat chez nous
Charleston Itinerary where to eat chez nous

Charleston Itinerary where to eat chez nous

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It’s Saturday morning, and you are well-rested and ready to take advantage of all of the sights, food, and activities Charleston has to offer. In the mornings, we love to either walk or ride bikes around South of Broad. We especially recommend this if you’re visiting during the summer, as temperatures haven’t reached their peak. The best way to see the city is by foot or by bike! So, pick from the variety of bikes 86 Cannon offers and enjoy the beautiful Charleston landscape. You can bike down to Black Tap Coffee for our favorite coffee in Charleston. The Iced Lavender Latte is our favorite. Next you can head to Colonial Lake, a beautiful public park, and from there, take Rutledge Ave to the South of Broad neighborhood. A wonderful place to end your biking/ walking tour of the city is under the shade of the trees at White Point Garden on The Battery. 


Charleston Itinerary where to go rainbow row

Charleston Itinerary where to get coffee black tap

Charleston Itinerary where to eat leons oyster shop
Charleston Itinerary where to eat leons oyster shop


We’re sure you are hungry after this tour, so head to one of our favorite brunch spots on the peninsula: Leon’s Oyster Shop..  Leon’s is definitely on the heartier side, as far as brunch options go, so if you don’t feel like one of their delicious fried options, such as their signature Fried Chicken, we also loved the Siam Salad.


Charleston Itinerary where to visit aiken rhett house
Charleston Itinerary where to visit aiken rhett house


After you enjoy Charleston brunch hour at Leon’s, we suggest going on a historical home tour at the Aiken Rhett House. This is one of the first tours we took when visiting and we learned so much about the history of the area through the self-guided walking tour of the property. Afterwards, you might want to head on over to King St for some shopping. A few of my favorites include Hampden Clothing and Lily. Hampden Clothing has an incredible list of designers like Sea, Ulla Johnson, Tibi, Stella McCartney, Isabel Marant, Zimmermann, Marni and more thanks to the owner, Stacy, and her carefully curated selections. It’s hard to walk out empty handed and the newly renovated space is gorgeous. Lily is a charming boutique inspired by French culture. They carry perfumes, scarves, jewelry, and deluxe home goods. It’s also fun to explore some of the art galleries in this area, including the beautiful Meyer Vogl Gallery.


Charleston Itinerary where to shop hampden clothing

Charleston Itinerary where to visit meyer vogl gallery
Charleston Itinerary where to visit lily shop


We know Charleston’s humidity may be catching up to you by now, especially if you are visiting during the summer months. Don’t worry, we have just the fix! After shopping on Lower King, walk up (or bike) to Upper King Street, where you will find Jeni’s Ice Cream. Jeni’s is one of our favorite dive-ins for a cold sweet treat. We try a different flavor every time we come in. 


Charleston Itinerary where to eat jeni's ice cream on king street

Charleston Itinerary where to eat dinner husk
Charleston Itinerary where to eat dinner husk


From there, take an uber or bike back to 86 Cannon for a glass of wine on the porch. Take some time to relax before you cap off this perfect day with an incredible dinner experience at Husk. You’ll want to make sure you have made your reservation in advance for Husk as they are known for being booked even a month in advance during busy travel seasons. (If you can’t get into Husk, see our Charleston Guide for more suggestions.) They have a bar in the carriage house next door where you can enjoy a cocktail before you are seated. After your meal, you might enjoy walking down the cobblestone roads off Queen Street. Take in the romantic spectacle of porches lit with gas lanterns before you head back to the hotel.


Charleston Itinerary where to eat breakfast hominy grill



You have a couple different options for breakfast Sunday morning depending on your travel schedule. If you are short of time, stop by The Daily or Callie’s Hot Little Biscuit for a bite before you have to leave town. If you have a little bit more time to kill, Hominy Grill is a great breakfast/ brunch spot whose menu is the epitome of a Southern meal (see above!). 


Charleston Itinerary where to eat callie's hot little biscuits
Charleston Itinerary where to get coffee the daily


Charleston 48 Hour Itinerary


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