For the past 10 years, Charleston has topped the list for the best small city by Conde Nast Traveler and it’s easy to see why. Whether you can’t wait to indulge in Southern comfort food, you want to bask in the sun on one of their beautiful sandy beaches, or you want to soak in the historical culture, Charleston is as picturesque as it gets. Three days is the perfect amount of time to experience the best this charming city has to offer, but we have a feeling you’ll be coming back again and again.
Where To Stay
French Quarter Inn ($$$)
Locals will “ooh” and “ahh” once they learn you’re staying at the French Quarter Inn. As the name of the boutique hotel suggests, it’s primely located in the center of the historic French Quarter, making it ideal for people who want to be within walking distance of the sites. You’ll instantly feel like an A-lister when you walk in and receive a complimentary glass of champagne (cheers!). The rooms are pretty spacious and are decorated with French flair, plus you’ll love surprise little treats like warm cookies and milk with your turndown service to make your stay feel homier. Enjoy a free breakfast (fresh berries, gourmet quiches, and more) in the lobby, outdoor terrace, or even directly in your room. Since everyone knows that sometimes it’s hard to truly get comfortable in a hotel room, their Sound Sleep Program lets you pick from a selection of comfortable pillows, provides sleepy tea, and lets guests complete a free sleep assessment for sweet dreams.
The Ryder ($$)
This stylish boutique hotel in the middle of downtown draws people in with its fab poolside bar (p.s. the pool is chic, but on the small side, so it’s not really a fit for kids). The rooms themselves are great, too: Earthy colors, retro-style furniture, custom-woven rugs, and a variety of wood all add to the boho vibe. The gym and spa are brought straight to your room thanks to our post-pandemic era — you can book an in-room treatment from a pro or even have Peloton bikes delivered to your room.
The Dewberry Charleston ($$$)
No detail was left behind in the eight-year renovation of this former federal building. The Dewberry, named after John Dewberry (a powerful real estate developer in the South), is quintessential Charleston with a lime-washed exterior, marble lobby, wooden walls, and period furniture. If you love great views, book one of the corner flats, which overlook the harbor. Make sure to make a reservation at the hotel’s spa, which incorporates the Southern native dewberry plant into each of their signature treatments. After you’ve worked up an appetite from borrowing one of the free bikes or hitting up a rooftop yoga class, check out the on-site Living Room restaurant for morning coffee, happy hour, or light bites.
Where To Eat and Drink
The Obstinate Daughter
After you’ve spent the day at one of Sullivan’s Island’s pristine beaches just 10 miles from downtown Charleston, grab a table at The Obstinate Daughter. The Southern restaurant is influenced by French, Italian, and Spanish cuisine to give you mouth-watering dishes that are dictated by what’s in season (think: peach salad, wood-fired pizzas, and gnocchi). A part of the restaurant’s DNA is being environmentally friendly — it received Green Restaurant Certification for its commitment to waste reduction, water efficiency, sustainable food, and other requirements. Open weekdays from 11 a.m. to 3 p.m. for lunch and 4 p.m. to 10 p.m. for dinner (11 p.m. on Fridays and Saturdays).
Daps Breakfast and Imbibe
If you’re the type where your eyes are bigger than your stomach, fair warning: It’s impossible to pick just one dish at these cozy digs. This casual breakfast shop serves up delicious items like fruity pebble pancakes, chorizo-filled breakfast burritos, sticky buns, breakfast banh mi, and more. Oh and breakfast beer? Totally a thing at Daps (there’s also cocktails, mimosas on tap, and sake Bloody Marys, too). Open daily (except Wednesdays) from 8 a.m. to 2 p.m.
The Ordinary
For a restaurant named The Ordinary, their food is anything but. A semi-finalist for the James Beard Award, chef Mike Lata is considered to be one of the trailblazers who helped shape the city’s amazing food scene into what it is today. The menu is all about beautifully presented seafood — the three-tiered seafood platter and oysters on the half shell are favorites. The extensive wine and cocktail menu is also part of the reason the multi-level dining room (which used to be a bank) fills up quickly. Open Wednesdays to Sundays from 5 p.m. to 10:30 p.m. and lunch on weekends from 12 p.m. to 5 p.m.
Chasing Sage
A quick scroll through this new restaurant’s Instagram page gives you an immediate glimpse into their vibrant, colorful dishes all inspired by Lowcountry ingredients. After the launch was delayed due to the pandemic and briefly pivoting to a pop-up, the restaurant is finally officially open. The menu aims to respect the land with small plates featuring carefully sourced veggies, meat, and seafood (mostly from their own farm) and a curated drinks list. The food constantly changes depending on what time of year you visit — and which chef you get. The two-chef kitchen is unusual for a small restaurant, but it allows for the team to be more creative about evolving the menu. Open Tuesdays to Thursdays from 5:30 p.m. to 10 p.m. and Friday and Saturdays until 11 p.m.
What To Do
Magnolia Plantation and Gardens
Travel + Leisure has called this spot one of “America’s Most Beautiful Gardens.” Founded in 1676, it’s also one of the oldest public gardens across the country. In addition to the garden, you can travel back in time on the plantation house tour, take a break from walking with the nature boat tour that glides through Magnolia Plantation’s former rice field along the river or visit the adjacent Zoo and nature center to view animals that aren’t usually seen in the wild. Open daily from 9 a.m. to 5 p.m.
Charleston City Market
This market is a good enough reason to bring an extra empty suitcase with you. It’s your one-stop-shop for local art, toys, clothes, and souvenirs. Head straight to the “basket ladies” who use West African techniques and local materials like sweetgrass to weave beautiful, hand-made baskets. There are also tons of places to grab a quick bite to eat and you’ll get to experience southern charm first-hand by getting to know the local entrepreneurs. Open daily from 9:30 a.m. to 5 p.m. and until 10:30 p.m. on Fridays and Saturdays.
Bulldog Tours
Whether or not you believe in ghosts, you’ll love the fascinating people and places you’ll discover through the entertaining stories told by your Bulldog tour guide. You can choose from a Charleston haunted jail tour to a graveyard tour to a haunted pub crawl and hear the haunted legends that date back to the late 1600s. The walking tours last about two hours and it’s a great way to get exclusive access to landmarks around town.
Rainbow Row
One of Charleston’s most Instagrammable spots? That would easily be Rainbow Row, a neighborhood featuring 13 pastel-colored houses on the waterfront. After the Civil War, the area was ragged and rundown until Judge Lionel Legge and his wife, Dorothy Porcher Legge, bought the stretch of houses and spruced them up into a pastel pink to make them more aesthetically pleasing. Over time, residents changed up the hues, and though each of the houses is privately owned, city law mandates that their pastel colors can’t be changed. You can visit any time of day, but be prepared to have to wait for an engagement or wedding photoshoot to wrap up.
