In many ways, Charleston is a lot like Martha’s Vineyard. It’s an old city, full of charm, character and history, that’s still incredibly popular today. There’s great food, amazing sights, plenty of things to do and good people to meet.
We love coming here because we always seem to make incredible memories while visiting. Whether we’re in town for a wedding, to reconnect with family and friends or to just enjoy a long weekend away, whenever we leave, we immediately eye our calendar to see when we can make it back.
So, if you’re looking to plan a trip down to Charleston, we wanted to share some of the items on our itinerary, which, as usual, is pretty packed. We hope to see you down there soon.
Charleston 101: What To Do
Stroll Down King Street
See the best of what Charleston has to offer by taking a leisurely walk down King Street. Start off at Marion Square and head due south—you’ll know you’re heading the right way if you pass our store! It’s just a little over a mile until you reach the southernmost point of Charleston, aka the Battery, and the ocean view is totally worth it.
A fun geography fact about Charleston: it’s a peninsula, so it’s almost entirely surrounded by water. Which means there are plenty of places to check out by boat, whether you’re cruising your own vessel or taking a tour of the harbor and the surrounding waterways.
Get ready to grip it and rip it! There are no fewer than 17 championship-level golf courses in the Charleston area. It doesn’t matter if you’re a scratch golfer or a weekend hacker, you’ll find all of the beautifully maintained courses challenging, fun and in a coastal setting that can’t be beat.
A Mt. Pleasant landmark, this coastal tavern and inn offers classic comforts with a bit of salty air (and a lot of delicious food). theposthouseinn.com.
The Dewberry Hotel
First-class amenities, award-winning dining and the best rooftop bar in the city. What else do you need? thedewberrycharleston.com .
Exploring Charleston’s Charm And History
Walking around Charleston, it’s impossible to not feel its history. From the narrow, cobblestone side streets to the stately rowhouses, it’s clearly an old town—and one with a rich, complicated past. Here are some of our favorite spots to explore to better understand and appreciate the people and places that have shaped the city.
History, With A View
Offering the best views of the Charleston Harbor since it was built in 1670, the Battery’s original purpose was to offer a strong defensive position against ships entering the area. The stunning lookouts remain, but now the park is known for its great people watching, old Civil War cannons and the White Point Garden, where on any given weekend, you’re bound to see someone getting married. Learn More.
Architecture In Color
Charleston City Market
Since it first opened in 1807 as a ramshackle collection of vendor sheds and low buildings, the Charleston City Market has undergone many expansions and renovations, but one thing has remained constant: it’s the cultural heart of Charleston. It’s a place where you can find local food and folk art, handmade souvenirs and a taste of coastal Carolina unlike anywhere else. Learn More.
Guardian Of The Harbor
America changed forever on April 12, 1861 when Confederate troops fired on the US garrison stationed inside Fort Sumter. Although heavily damaged during the Civil War and never completed as intended, the fort is now a national monument, where history buffs can explore the ruins and learn about the people and events that brought about this defining moment in our nation’s past. Learn More.
For a true Charleston experience, here are some additional highlights in and just out of town you won’t want to miss.
The Can’t-Miss Photo Op
There’s a good chance you’ve seen this multi-layered, pineapple-shaped fountain in images and videos before. And for good reason: it’s an iconic Charleston landmark. So, do the touristy thing and go snap your own selfie in front of it—and enjoy the waterfront park while you’re at it.
Architecture In Color
This bakers’ dozen of brightly colored, historic row homes situated along East Bay Street dates back to 1740. Complementing the striking aesthetic of each Georgian house is an equally compelling story. Not just something for architecture fans to check out, as the walk up and down this stretch of Charleston offers plenty of sights, shops and attractions.
Isle Of Palms
While Charleston proper doesn’t offer much in the beach category, it’s easy to find some sand and sun just outside of town. Isle of Palms is about a 40-minute scenic drive from downtown and offers seven miles of pristine beaches for every sort of surfside fun.
Visitors looking for a place to spend a day during their trip to Charleston should check out Sullivan's Island. Don’t let its designation as a “suburb” fool you: there’s plenty to do here, including stunning beaches, delicious dining and even a gateway back in time, with the Revolutionary-era Fort Moultrie, which is now a National Historic Park.
Our Favorite Upcoming Events
APR 28 - MAY 1
Charleston Race Week
Now in its 25th year, Charleston Race Week is one of the preeminent regattas in the East Coast sailing calendar. Established in 1996 by members of the Charleston Ocean Racing Association, the regatta has grown over the years from a handful of local sailors to hundreds of racers from all over the world, from weekend warriors to professional racing programs. If you can’t get on the water for the action, it’s always a great time to visit the town. Learn more at
SEP 9 - SEP 19
Charleston Restaurant Week
Come hungry, folks. This is a foodie’s dream as many of the city’s finest restaurants offer prix fixe lunch and dinner options starting at $20. It’s the perfect opportunity to experience what lowcountry cuisine is all about. Whet your appetite at restaurantweeksouthcarolina.com/city/charleston_area.
OCT 7 - NOV 6
The Fall Tours
Charleston residents have a deep connection to the town’s historic homes. Every fall, the Preservation Society of Charleston hosts private home tours, inviting guests to visit a handful of famous and notable houses in various parts of the city. Informative and entertaining, each tour is full of interesting architectural tidbits and local folklore. Learn more at preservationsociety.org.
An annual festival filled with live music, carnival games, local artists, tasty food and more, all for a good cause: raising money for local cancer patients. Walk down Center Street in Folly Beach to take it all in, then finish the day by relaxing by the ocean. Get ready for the party at follybeach.com/follypalooza.
We all have those special places we love to visit. The ones where cherished memories are made and lasting friendships are formed. The spots we return to, year after year, as a getaway from the day-to-day and as a reminder that Every day should feel this good. Charleston is one of those places for us.
We’d love to see your Charleston moments, from past visits or an upcoming trip. Post a picture or story on Instagram sharing your favorite photos and memories @vineyardvines or @vineyardvineswomen for a chance to have your post featured on our account. And, who knows, it may even inspire our next collection or adventur
Enter Delivery Address
P.O. Boxes are not eligible for same day delivery.