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With its colorful buildings, vibrant foodie scene and sandy beaches, Charleston is one of those destinations that has a bit of everything and is perfect for a long weekend. The city also happens to be just a two-hour flight from New York, so if you live in the Big Apple like me, it’s an easy trip if you can’t get much time off work. 3 days in Charleston are enough to cover the best things to do there and eat at some of the city’s best restaurants. Plus, the weather is much milder down in the south, with plenty of warm sunny days!
If you’re planning to spend a weekend in Charleston, here’s my suggested Charleston itinerary:
Day 1: Historic Downtown, Waterfront & Rooftops
On day one of your Charleston itinerary I’d suggest getting acclimatized by walking around the downtown area. Charleston is small and easy to explore on foot.
Joe Riley Waterfront Park
Start by strolling through Joe Riley Waterfront Park, which has two fountains and romantic waterfront views. The park runs for about half a mile along the Cooper River and won the 2007 Landmark Award from the American Society of Landscape Architects and the National Trust for Historic Preservation.
A highlight is the Pineapple Fountain, which is a popular place for kids to cool off and paddle when the weather gets hot.
Once you’ve walked through the park, head to Rainbow Row on East Bay Street, which is an iconic row of colorful Georgian-style houses that date from 1748 to 1845. The houses were owned by the merchants who operated their businesses on the ground floor.
This is the cutest spot in Charleston for Instagram photos and engagement shoots so don’t be surprised if you have to wait your turn to grab a photo.
An interesting fact for you – the houses haven’t always been brightly colored. The color trend started in 1931 When Dorothy Porcher Legge and her husband Judge Lionel Legge purchased a section of the houses and decided to paint them in pastel hues. Other neighbors followed suit, and it eventually became known as Rainbow Row!
Old Exchange and Provost Dungeon
Next up on your Charleston itinerary, take a walk to Old Exchange and Provost Dungeon, which was built in 1771 as a commercial exchange and custom house. This historic building has functioned as many things over the last two and a half centuries, including a commercial exchange, custom house, post office, city hall, military headquarters, and museum. Admission to the building includes a guided exhibition of the top two floors of the building and a 25 minute guided tour of the cellar, known as the Provost Dungeon.
Admission is $12 for adults and $5 for children age 6-12. Children under 6 enter for free.
Old Slave Market Museum
If you interested in learning about Charleston’s dark history of slavery, you can visit the Old Slave Mart Museum nearby, which is a building in the French Quarter where slaves were auctioned before the Civil War. The self-guided tour is a sobering experience and takes less than an hour, where you’ll read informative posters about South Carolina’s slave history.
Charleston City Market
Afterwards make your way to Historic Charleston City Market – a large indoor market that spans four city blocks and dates back to the 1790s. Here you’ll find lots of different vendors and stalls selling artisanal products.
By this point you’ll probably be feeling like it’s time to rest for a while, so I’d recommend visiting the rooftop at The Dewberry Charleston hotel, called Citrus Club. The stunning rooftop terrace is the highest in Charleston and offers incredible views over the city. Make sure to wear smart casual attire though, and note that collared shirts are required for men.
Dinner at Husk
For dinner, grab some Southern cuisine at one of Charleston’s acclaimed restaurants. There are so many great options, but Pearlz, Magnolias and Husk were all recommended to us by locals. We ate at Husk, which is housed in a Victorian-era home and serves locally sourced Southern dishes with a modern twist. The food was excellent and so were the cocktails!
Day 2: Beach and Sunset at Shem Creek
On the second day of your weekend in Charleston I’d suggest hitting the beach!
Folly Beach near Charleston is very popular, although our Uber driver warned us against it just because the traffic can get really bad on weekends. If there’s no traffic the journey should take 20 minutes but at peak times he told us it can take over an hour to get there and back. Instead, I’d suggest going to Sullivan’s Island, which is a bit closer to the city.
Sullivan’s Island is a great beach, located next to the Isle of Palms and at the mouth of Charleston Harbor. The beach is wide and sandy, and there are several great restaurants just a 5 minute walk away. On windy days you’ll often see kiteboarders surfing over the waves.
I’d definitely recommend getting food and drinks at Poe’s Tavern, which is named in honor of the poet Edgar Allan Poe. Poe’s is relaxed but fun, serving burgers and American fare on its busy outdoor patio. The Bloody Mary cocktails here are great and are basically a meal in a glass!
If you do decide to venture as far as Folly Beach, there are numerous great dining options there, including The Crab Shack, Lost Dog Cafe, Rita’s Seaside Grille and Jack of Cups Saloon.
After soaking up some sun on the beach, drive to Shem Creek and watch the sun go down at Tavern & Table. This waterfront restaurant has both indoor and outdoor bars with scenic views of historic Shem Creek. The menu features lots of small plates which are ideal for sharing – my favorite of which was the Burnt End Mac & Cheese! From their mains I also really loved their Ahi Tuna Bowl.
Day 3: Plantation Tour or Ghost Tour
On day 3 in Charleston you could visit a plantation or do a ghost tour. There are several plantations in the area, including Magnolia Plantation and Gardens, Boone Hall Plantation & Gardens, and Middleton Place. Magnolia Plantation and Middleton Place are rather close to each other, so it would make the most sense to drive out and visit these two at the same time.
Boone Hall Plantation
Boone Hall Plantation is the plantation where Blake Lively and Ryan Reynolds had their wedding. There was huge controversy over them holding a wedding on a site that kept slaves, which resulted in them apologizing to the press and public.
The plantation was founded by Englishman Major John Boone in 1681 and covers an area of 738 acres on the banks of Wampacheone Creek. The plantation has a beautiful garden featuring antique roses that are over 100 years old as well as a butterfly garden containing lots of beautiful butterflies. You can tour the plantation on a 40 -minute tractor tour and see the plantation’s Black History in America exhibit, which is housed in nine former slave cabins.
Located about 15 miles northwest of Charleston, Middleton Place is home to the oldest landscaped gardens in the United States. Occupied by the Middleton family for several generations, the plantation spans 110 acres and is designated a National Historic Landmark. Through self-guided or guided tours, you’ll learn all about the Middleton Family as well as the generations of slaves who lived, worked and died at Middleton Place. A tour called “Beyond the Fields: Enslavement at Middleton Place” facilitates a conversation about slavery in American history. Admission to the plantation costs $26 for adults if you buy your tickets online, or you can buy them at the gate for $29.
Founded by the Drayton Family in 1676, nearby Magnolia Plantation also has very beautiful gardens and was selected by Travel + Leisure Magazine as one of “America’s Most Beautiful Gardens”. In addition to the house and gardens, the plantation site now features a nature tram, zoo, cafe and gift shop. Boat tours depart throughout the day, taking visitors on Magnolia’s old flooded rice field along the Ashley River. Admission to the plantation costs $20 for adults, $10 for kids and children under 5 are admitted for free.
Another option for the final day of your 3 days in Charleston is to take a ghost tour. Bulldog Tours offers a variety of tours that will show you all things spooky and supernatural in Charleston. You can take a behind-the-scenes tour of the Old City Jail, which housed some of Charleston’s most infamous criminals, or walk around Charleston’s oldest graveyards after dark.
The company even runs a haunted pub crawl, which takes you to some of Charleston’s notable pubs and taverns to learn the tales of the ghosts that wander the city streets.
Once you’ve driven back to the city it’s time to try out another restaurant. With so many great ones in the downtown area, you’re spoilt for choice. We ate at an Italian restaurant called Le Farfalle, where we ordered the Octopus Carpaccio and the Whipped Ricotta.
However, I also had my eye on Chubby Fish, FIG, 167 Raw Oyster Bar and Fleet Landing. If I go back to Charleston I’ll definitely be trying those out! Many restaurants in the city have been featured in well-known food magazines and several restaurants in Charleston are winners of the James Beard Award, including FIG, Husk and Rodney Scott’s BBQ.
Where to Stay on Your 3 Days in Charleston
Charleston has plenty of nice boutique hotels in the historic downtown area, although they tend to be more expensive and don’t have pools. I’d recommend staying just across the water in Mount Pleasant so you have the option of relaxing by a pool if it gets too hot.
Hotel Indigo – I stayed at Hotel Indigo in Mount Pleasant – a boutique hotel with a palm tree lined pool. It’s only a bridge away from Charleston, so it’s easy to get in and out of the city. Book your stay at Hotel Indigo here.
Shem Creek Inn – Located in Shem Creek, this hotel is right next to popular eateries such as Tavern and Table and Red’s Ice House. The pool is right on the water and many of the rooms have views of the creek. I love that Shem Creek Inn offers special packages to entice customers including things like free koozies and a six pack of craft beer! Book your stay at Shem Creek Inn here.
The Dewberry – If you’re looking for style and luxury, The Dewberry is one of the best hotels in Charleston. The airy guest rooms feature hardwood floors, leather wingback chairs, Irish linens and bathrooms wrapped in Danby Vermont marble. Plus you’re only a short elevator ride away from Charleston’s best rooftop bar, Citrus Club. Book your stay at The Dewberry here.
Emeline – Located in Charleston’s historic district, Emeline is a chic boutique hotel featuring a wood-fired eatery, café and coffee shop, courtyard and fitness center. Rooms are tasteful, with thoughtful touches such as Amber Wood Red Flower bath amenities, custom embroidered linens, plush towels from Matouk and custom ceramic bath accessories designed by local artist Susan Gregory. Book your stay at Emeline here.
Getting Around on Your 3 Days in Charleston
The best way to get around on your weekend Charleston is by renting a car but since we were only there for 3 days we opted to get around by Uber and Lyft.
Maybe we’re just spoiled living in New York but we found that there weren’t many cars in Charleston and we were often waiting a long time for a ride. We soon learnt it’s best to ride with Lyft and pre-book a ride in advance to ensure that a car comes when you need it.
If you plan to rent a car from the airport, Discover Cars or Rentals.com are good sites for finding cheap rentals.
When to Visit Charleston
Charleston experiences mild winters and hot summers. Spring runs from March to June and is the best time to visit, when the flowers are in bloom and the weather is warm and sunny.
Summer is more tropical, with thunderstorms occurring in the afternoon. Autumn is also a nice time to visit, when Charleston experiences clear blue skies, sunshine and crisp, cooler evenings.
Winters are generally mild but there’s still the chance of the odd snow shower in December and January.
A Final Word…
I hope you like this Charleston itinerary! 3 days in Charleston is the perfect amount of time to see this adorable city and also make it out to the beach. It’s one of the best southern cities to visit in the USA and has some really great restaurants, so if you’re a foodie you’ll definitely enjoy a weekend here. Charleston is also a student city with very cheap drinks and lots of bars, so if you’re visiting on a weekend you’ll find plenty of nightlife.
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