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Ultimate 3 Day Charleston Weekend Getaways: Your Perfect Itinerary

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Charleston, South Carolina, is a spring of culture and history in the South. From locally crafted treasures sold in historic marketplaces to breathtaking historical monuments to gorgeous beaches, visiting Charleston will enrich your knowledge, deepen your understanding, and feed your soul. (Oh, don’t worry. Charleston will keep your stomach fed, too).

Let’s start your 3-day itinerary for a Charleston weekend getaway in the historic district of downtown Charleston.

Day 1: Explore Charleston’s Historic District

Courtesy of Baker Manning

I don’t know about you, but I like to start a day of exploring with a good breakfast. So get a hardy southern breakfast at Toast! All Day to fuel your day of exploration in the historic district. Now, head outside for a stroll down King Street.

Stroll Down King Street

Walking down King Street, you’ll find yourself immersed in the beating heart of historic Charleston. The street is packed with shops and boutiques–but the charm of King Street extends beyond shopping

The architecture is rich in history, and there are plenty of landmarks, like Philadelphia Alley and Chalmers Street, that you can explore at your own pace. 

Joe Riley Waterfront Park

After shopping on King Street, head to Joe Riley Waterfront Park, a beautiful urban park in downtown Charleston. This park is the perfect place to relax and enjoy the stunning waterfront views and the city skyline. As you walk along the park’s pathways, you’ll find plenty of spots for people-watching 

One of the main attractions is the iconic Pineapple Fountain, a symbol of Charleston’s hospitality. 

Rainbow Row

Cobblestone streets and pastel-colored homes transport you back in time as you enjoy a leisurely stroll down Rainbow Row on East Bay Street. Dating back to 1740, this series of thirteen colorful historic houses was repainted in the 1930s to keep them cooler during southern summers.

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Historic Charleston City Market

Courtesy of The Charleston City Market

Then, visit the historic Charleston City Market, founded in 1807. Here, you can find everything from Bev’s hand-woven sweetgrass baskets to steampunk jewelry from Copper Lining and other local artisan wares that are certified 100% locally sourced and created. The market is a perfect spot to pick up unique souvenirs and sample some local flavors.

Ghost Tour in the French Quarter

As night falls, embark on a spine-chilling ghost tour in Charleston’s French Quarter. The French Quarter is home to numerous ghostly tales and historic sites. The tour takes you through narrow streets and dark alleys, where you’ll hear stories of restless spirits and mysterious happenings.

One of the highlights of the tour is the Dock Street Theater, reputed to be one of the most haunted buildings in Charleston. There have been hundreds of routine sightings, and two people in particular frequent the theater. 

Other notable stops include the French Huguenot Church and various historic homes.   

Where to park: 

  • Charleston Parking Garage
  • Cumberland Street Garage

A note on parking: All parking garages owned by the city cost $1 per half hour with a maximum cost of $18 per day. There’s limited free parking on the street, but only after 6:00 pm. Note that the visitor center’s parking garage has a shuttle you can take around town free of charge.)

Places to eat:

  • Toast! All Day
  • Magnolias Southern Restaurant 
  • Pizza Di Giovanni 
  • Henry’s on the Market

Kid-friendly?

  • Today is mostly kid-friendly with a lot of fresh air and walking. So if your kids are younger, be sure to pack that stroller – and the snacks.
  • Leave the younger kids at the hotel before you start the Ghost Tour at dusk.

Day 2: Rediscover History

Let’s talk about kids and history real quick. I, for one, love sharing our history as a country with our kids. And there are lots of historical learning opportunities in Charleston that are appropriate for all ages. 

Give your kiddos a glimpse into our first victory as a country. Show your kids how a group of individuals put aside their own self-interests and risked everything to be free in the Battle for Charleston Harbor. But don’t stop there. 

If we’re going to share our history, we have to share all of it – even the parts we aren’t proud of. Charleston was also an epicenter for the Slave Trade and the cradle of the Confederacy from which succession spread.

History is not about cold buildings and old artifacts. It’s about the people who used them, and they did not always use them for good. Day 2 is about sharing our history – all of it. 

A note to parents: You know your children best, so only you can decide if your children are ready to hear about the dark portions of our history. If you need some lighter moments in history, skip the Old Slave Mart and instead take them to visit Charleston Harbor’s monument. Then, tell them about the battle that gave hope to the Revolutionary War

The Old Slave Mart Museum

Courtesy of Road Trip America

Yesterday, we visited the historic Charleston Market, which is full of vibrant art and trade. Today, we visit a darker market, where the storage stalls have bars and the goods are chained. 

The Old Slave Mart Museum offers a poignant look into our past and the realities of the US slave trade in Charleston. It is housed on the site of the original Ryan’s Mart Slave Auction in downtown Charleston. The auction operated from 1856 until the Union Army shut it down in 1863. 

Being able to stand in the places where the slaves stood to be sold, to see their conditions as they awaited their fate, allows kids to better understand the depths of the depravity that the slave market brought to our shores. And now, as a place of remembrance, the Old Slave Mart Museum honors the lives of the slaves who passed through its cells by telling their stories.

Fort Sumter Tour

Your next stop is a tour of Fort Sumter. This historic site marks the beginning of the Civil War, where Confederate troops fired the first shots in 1861. To get to Fort Sumter, you take a 30-minute boat ride through Charleston Harbor, and you get an idea of what those sieging Fort Sumter had to go through. (You’ll also get some amazing photo ops as you can catch stunning views of the city from the viewpoint of the harbor.) 

Upon arrival at Fort Sumter, you can take a tour with a National Park Service Ranger and listen to all the historical details of Fort Sumter and its strategic significance in the Civil War. 

After that, you’ll have about an hour to explore the grounds. Yep, your kids can explore freely. I personally find this is the best way for my kids to brush up on US history because as we’re walking around, they rapid-fire questions, especially with sites that are as well-preserved as this one. My kids see the remnants of the fortifications and ask…

  • What’s that?
  • Why is that there?
  • What does that do?
  • Did they really shoot people with that?
  • Why would they do that? 

And – even though I’m utterly exhausted by the end of it – I answer their questions. (Okay, so Google does most of the answering, but I still have to read it to them, so it counts.)

I love their inquisitiveness because it shows me that they’re engaged and want to learn more. So take it from my family: This Fort Sumter is a must-visit. 

Charleston Museum

Established in 1773, the Charleston Museum is the oldest museum in the United States. As you can imagine, this museum is a treasure trove of artifacts and exhibits that chronicle the history of Charleston and the surrounding region. From prehistoric times to the modern era, the museum offers a comprehensive look at the early settlers to the American Revolution to the Civil War to the antebellum period, and the great depression. You get a case study of what American History in the South looks like. 

But it also has a whole exhibit for kids. It’s called Kidstory, and it’s an exhibit that stretches from the beginning of Charleston to the present day filled with interactives, historical recreations, and live storytellers. This exhibit is appropriate for children of all ages.

Places to park:

  • Camden Parking Garage
  • Midtown Parking

Places to eat: 

  • Halls Chophouse
  • The Darling Oyster Bar
  • 39 Rue de Jeun

Kid-friendly?

  • Yes, depending on your children’s ages. 
  • Both Fort Sumter and the Charleston History Museum are enjoyable for kids of all ages.
  • Older kids (8+) will learn from the Old Slave Mart. There’s nothing explicit there. But if you know your child is highly empathetic or easily impacted by others’ pain, you may want to wait until they’re older. 

Day 3: Outdoor Adventures and Relaxation

After two days of exploring Charleston’s rich history and vibrant culture, it’s time to lighten up, unwind, and enjoy the great outdoors. Day three is about beauty and relaxation. 

Boone Hall Plantation

Courtesy of CharlestonCVB

Established in 1681, Boone Hall Plantation is one of the oldest and most picturesque plantations in America. The plantation’s famous Avenue of Oaks, lined with ancient live oak trees, creates a breathtaking entrance that sets the tone for your visit.

Visitors can explore the plantation’s beautifully maintained gardens and historic buildings, including the original slave cabins that provide a sobering reminder of the site’s past. Your kids will enjoy the tractor tour that takes you around the plantation, as well as the hands-on education classes that will teach them about the life and economics of running a plantation in the colonial period.

Folly Beach

Folly Beach is ideal for those looking to unwind in a beautiful coastal setting. Known for its laid-back atmosphere and stunning natural beauty, Folly offers kayaking, fishing, and, of course, relaxing in the water and building sand castles on the beach. 

The beach’s sandy shores and gentle waves make it an ideal spot for families with young children. Spend your day basking in the sun and explore the local seaside shops and eateries. Folly Beach’s welcoming vibe and scenic views provide the perfect wrap-up for your weekend trip.

Rooftop Bar Experience

Cap off your Charleston weekend at one of the city’s renowned rooftop bars for a unique and enjoyable experience. Charleston’s rooftop bars provide stunning views of the city skyline and harbor, perfect for unwinding at the end of your trip. 

The Rooftop at The Vendue and The Watch Rooftop Kitchen & Spirits are two local favorites. These venues offer spectacular views and a variety of delicious cocktails and small plates.

Where to Park:

  • Various parking lots are available along the beach. Pay by hour.
  • Concord Cumberland Parking Garage

Where to eat:

  • Rita’s Seaside Grille
  • Lost Dog Cafe
  • Bowens Island Restaurant
  • Stars Rooftop and Grill Room
  • Rooftop at the Vendue
  • The Watch Rooftop Kitchen & Spirits

Kid-friendly?

  • Definitely! Your kids are going to love day 3 – less learning and more playing on the beach. 
  • But leave them at the hotel when you enjoy your dinner at the rooftop bar. (I didn’t have to tell you that, right?) 

Summary

Now that you’ve used this Charleston itinerary to its fullest, you may find yourself wondering, “What would it be like to move to Charleston?” If you’re thinking about a more permanent move (three days just isn’t enough for some), you may need to stay in a rental until you find a permanent resident. But where do you store your stuff while you’re waiting?

Check out Neighbor, a peer-to-peer storage marketplace, where you’ll find affordable self-storage options – even in neighborhoods with a high cost of living. 

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The post Ultimate 3 Day Charleston Weekend Getaways: Your Perfect Itinerary appeared first on Neighbor Blog.


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