Weekend in Charleston Itinerary: Perfect for 2-3 Days

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Full of charm and history, Charleston, South Carolina is easily one of the most interesting places we have visited on the East Coast! So, if you are looking to plan your weekend in Charleston, SC (2- 3 days), I am going to be sharing the best things you won’t want to miss in the Holy City!

I have also included travel tips, where to stay, and food options.

Rainbow Row in Charleston SC is one of the coolest things to do
Weekend in Charleston SC 3 days
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Day 1: Boone Hall, Historic City Market, French Quarter, King Street

Starting day 1 in Charleston with a bang, wake up nice and early because we have a lot of ground to cover! From Plantations, the French Quarter, and Historic Sites, this will be a fun and eventful day.

Boone Hall

First, let’s start the day with a small road trip to the Boone Hall Plantation. Some of you might recognize it from the movie the Notebook. Located in Mount Pleasant, it is around a 25-30 minute drive from downtown Charleston. 

Avenue of Oaks in Charleston

Boone Hall was built-in 1681, and is what you can expect for a classic southern plantation. You will drive down the classic southern driveway lined with giant oak trees covered in Spanish moss. 

During your visit, you will also have the opportunity to learn a ton of history about life on the plantation, the history of the house, and more. Charleston is a city that was mainly built by slaves. This was integral to the wealth of this city during the times. The prized crops of South Carolina were Carolina Gold (rice), the harvest of indigo, and cotton. 

While at Boone Hall, there are tour options that are included with your entry ticket. The most popular tours at Boone Hall include learning about the Gullah Culture, Historical Dwelling History Talk, and the House tour. We took several tours and felt the tours were done really well in explaining the dark history of the plantation. 

Additionally, they are dog-friendly, besides pets coming into the house.

Find Boone Hall tickets here.

Admission: $28 USD ages 13 – 64; $25 ages 65+; Free for children under 13. 

Hours: Monday – Saturday – 9 AM-5 PM; Sunday – 12 PM-5 PM

Address: 1235 Long Point Rd, Mount Pleasant, SC 29464

Entrance to Boone Hall Plantation in Charleston
Front of Boone Hall Estate in Charleston

Historic City Market

You have likely worked up a bit of an appetite, so next, you can head to the Historic City Market. This very popular complex expands 4 blocks. If you drove (like us), this is a great place to find metered parking.

The Historic City Market has been around since the 1790s and has tons of food and shopping throughout. You can find local Charleston goods, including the famous sweetgrass baskets, and fix your craving for delicious Lowcountry cooking. Additionally, they have outdoor tables if you just feel like relaxing your feet a little.

You may hear some call this the Old Slave Market and may wonder if slaves were sold here. The current knowledge is that slaves were never sold here, however, it supposedly got the name because many slaves shopped here.

Philadelphia Alley

Just a short walk from the Historic City Market, make your way into the French Quarter and stroll down Philadelphia Alley. This beautiful alley is covered in greenery and has a cute red brick walkway. It was one of my favorites to visit.

Philadelphia Alley can be found behind Saint Philip’s Church, and you can enter from Queens Street or Cumberland Street. 

Charleston Fun Fact: This alley has been dubbed Duel Alley because it was said that so many people would have duels here. 

Want to explore more of Charleston’s hidden alleys? Then check out this highly-rated hidden alley tour.

Philadelphia Alley in Charleston

Saint Philip’s Church

Continue on your walk to Saint Philip’s Church. Another National Historic Landmark of Charleston, this church was built in 1838. This is actually the 3rd version of the church. The original was actually a wooden church built on Broad and Meeting St., however, it was damaged by a hurricane. 

Then, it was built in this location but was damaged by a fire, so this is the 3rd one. The iron in the front is still original! 

Psst… If you are really interested in history, the Powder Magazine is just around the corner. It is the oldest standing public building in South Carolina and is where the gunpowder was stored and supplied for the American Revolutionary War and the Civil War.

St. Phillip's Church Charleston

French Huguenot Church

From Saint Philip’s Church, you will be able to see the French Huguenot Church, which is likely one of the prettiest churches in Charleston. If you are looking for Instagrammable places in Charleston, this is certainly one of them. 

Built in 1844, this Gothic Revival Church is colored pastel pink with lovely iron gates and palm trees around it. A quick stop here to admire the beauty is all you need.

The French Huguenot Church in Charleston

Dock Street Theatre

Moving right along, just take a couple of steps forward from the French Huguenot Church, and you will see the iconic Dock Street Theatre! Charleston decided to put a lot of the landmarks right next to each other, making our weekend itinerary easy! 

Dock Street Theatre Charleston Weekend itinerary

Believe it or not, the Dock Street Theatre was the first building in the USA that was built exclusively for theatre. It opened in 1736! Unfortunately, this is no longer the original building, but it is in the same spot. Due to a few fires, the original building was destroyed.

Throughout history, the theatre has opened and closed. At one time, the building was the Planters Hotel. Present-day, it has been restored to its former theatre glory and can be enjoyed today! You can admire it from afar, take a tour inside, or even go see a show! See what is playing at the Dock Street Theatre here!

The Dock Theatre - Woman in pink skirt standing in front

Pink House Gallery – AKA The Pink House

Are you ready to see one of the most charming streets in Charleston? Continue walking down Chruch Street and turn onto Chalmers Street. Chalmers Street is home to the famous Pink House.

This cute little home is one of Charleston’s oldest homes and was frequented by pirates! You read that right! It was a tavern that was also possibly/slightly a brothel, being that some ladies of the night had their addresses here.

On top of that, it is also known to be haunted. So, you get a little bit of everything when seeing this charming little home. 

The Pink House on Chalmers Street in Charleston is one of the best places to see

Old Slave Mart Museum

Right up the Ballast Stone Street in Chalmers is also the Old Slave Mart Museum. This is a great place to learn more about the dark history of Charleston and the role slavery played here.

The Old Slave Mart opened in 1856 and was a place where enslaved African Americans were sold. 

Thankfully, in 1938, the Old Slave Mart was turned into a Museum. It is now Charleston’s oldest museum of African American history and the first museum on the history of slavery in the USA. During a visit, you can find artifacts, transcripts, and more. Keep in mind they are closed on Sunday! 

Hours: Monday – Saturday: 9:00 AM – 5:00 PM

Admission: General Admission: $8 USD; Child (7-12): $5

Address: 6 Chalmers St, Charleston, SC 29401

Front of the Old Slave Mart Museum in Charleston

Washington Park

It is a good thing you are wearing your walking shoes because we are now taking a short stroll through Washington Park. Here, you will find some monuments and a place to sit and rest your feet if it is nice out, or even enjoy some shade under the oak trees. Charleston can get HOT!

In the center is a miniature version of the Washington Monument in DC. This park is also right along the way to our next stop on this Charleston itinerary. 

Address: 80 Broad St, Charleston, SC 29401

Washington Park with two monuments and trees in Charleston

The 4 Corners

Feel like a true Charlestonian and tell people you are at the 4 corners. Located on Meeting Street and Broad Street, this intersection was dubbed the four corners of law because, on each corner of the intersection, you will find a law institution, whether it be state, local, or religious.

The 4 buildings on each corner are  Charleston City Hall, St. Michael’s Episcopal Church, the Charleston County Courthouse, and the United States Post Office and Federal Courthouse.

Charleston Insider tip: If you want to grab a bite nearby, Poogan’s Porch is a 4-minute walk and one of the most well-known places to get great southern comfort food. 

The top of Saint Michael's Church with some palm trees
View of Saint Michaels

King Street

Known as one of the top shopping districts in the USA, make sure to add a visit down King Street to your itinerary. With high-end shopping, dozens of restaurants, clubs, and more, this is the area that really feels like the city. King Street is pretty long, but the closer you get to the Battery, the more residential it gets. 

If seeing more mansions was on your list, then you might want to head this way. King Street is probably the busiest area while in Charleston, and finding parking will be much harder. If you did bring a car, taking a drive down King Street can be pleasant.

King Street mansion in Charleston with lots of greenery

Night Activities in Charleston

Day one has been very busy and full of sightseeing, but if you love to see a lot within a short amount of time, here are some night activities to add to your Charleston itinerary as the sun is going down. Some fun things to consider doing in Charleston are: 

You can spread these night activities throughout the 3 days in Charleston.


Day 2: Pineapple Fountain, Rainbow Row, Historic Homes, The Battery

On day 2, we will be exploring some beautiful historic homes, iconic landmarks, charming alleys, and more! Make sure you are wearing comfortable walking shoes because we are going on a free walking tour that I have personally curated for you below!

If you do choose to drive, you can also find parking around Charleston however, most locations are just a couple of minutes walking from one another.

The Pineapple fountain is a top photo spot in Charleston. Woman in Yellow maxi dress and straw hat

Joe Riley Waterfront Park

Start your day with a stroll through Joe Riley Waterfront Park. This iconic park is located right on the Cooper River. The park is most notable for the famous Charleston Pineapple Fountain. The Pineapple is a symbol of hospitality, and little pineapples can be found throughout the city.

During the summer, people wade around in the fountain, which totally makes sense since Charleston summers are brutal! Visiting the Waterfront Park is considered one of the best things to do in Charleston! The park opened in 1990 and consists of 12 acres. This is also a great spot to relax for sunset as well! 

The Pineapple Fountain in Charleston

Old Exchange and Provost Dungeon

Next, head to the historic Old Exchange and Provost Dungeon. It is about a 4-minute walk from The Pineapple Fountain at Joe Riley Waterfront Park. Does seeing a real-deal pirate dungeon pique your interest?

The Old Exchange and Provost Building is probably most known for being a place where British Soldiers held American Soldiers and pirates during the American Revolutionary War.

Built between 1767-1771, this National Landmark was also used as a commercial exchange, custom house, post office, and city hall. Today, you can tour the building as a museum and see the dungeon!

Hours: Monday – Saturday: 9 AM – 5 PM; Sunday: 11 AM – 5 PM

Admission: Adults: $12; Children (6-12): $5; Children (0-6): Free

Address:122 East Bay Street Charleston, SC 29401

Old Exchange and Provost Dungeon weekend in Charleston SC

Rainbow Row

You can’t spend a weekend in Charleston without seeing rainbow row. Famous on Instagram, this row of 13 colorful homes has a way to brighten your day. From the Old Exchange, it is no more than a two-minute walk going down E Bay St. between Tradd Street and Elliot Street.

Make sure to have your camera with you! This part of town was actually transformed because of these colorful homes. The area was considered an undesirable part of town after the Civil War.

Then, in 1931, a real estate agent purchased several homes and painted them bright pink. Before you knew it, other owners followed suit, and the curb appeal brought people in!

Rainbow Row is one of the most Instagrammable places in Charleston. Woman in Yellow Skirt and straw hat
Rainbow Row. Woman in street with orange skirt

Nathaniel Russel House

From Rainbow Row, you will want to turn on Tradd Street and enjoy some of the beautiful homes until you hit Meeting Street. This is where we will be going to see the Nathaniel Russel House. This is about a 5-minute walk. You can choose to go inside and tour the home or enjoy the gardens for free! 

Touring inside the home will be for you if you love looking at antique art and love Neoclassical architecture. The home was built in 1808 for Nathaniel Russel, who was a slave merchant. Oh, and there is even a “free-flying” 3-story spiral staircase.

It is now owned by the Historical Charleston Foundation, which has opened the home up to the public. 

Hours: Open Daily from 10 AM – 5 PM (4:15 PM is the last tour).

Admission: Adult: $15.00; Child 6-16: $7.00; Under 6 is free.

Address: 51 Meeting St, Charleston, SC 29401

Side of the Nathaniel Russell home
The Nathaniel Russell house is one of the best things to do

The Williams Mansion – Also Known as The Calhoun Mansion

Continue your stroll down Meeting Street, where you are sure to see some more stunning homes until you reach The Williams Mansion, also previously known as the Calhoun Mansion – a 4-minute walk. Even if you don’t go inside (tours have been temporarily closed), it is still worth adding to your Charleston itinerary.

In the front of the home, you can even see an old carriage stone for the women to get into the carriages back in the day. Usually, you can find the carriage stones in front of the most prominent homes. 

It is the largest private home in Charleston, SC coming in a 24,000 sq ft. with over 30 main rooms. To think this home cost $200,000 to build it back in 1876. 

Until recently, the Mansion was referred to as the Calhoun Mansion. The name was adopted when the home was passed down to Williams’s son-in-law Patrick Calhoun. Throughout the home’s history, it passed through several hands and was even a hotel at one point. 

Hours: Tours are temporarily closed. 

Address: 16 Meeting St, Charleston, SC 29401

The Williams house is one of the most Instagrammable places in Charleston SC

The Battery and White Point Garden

Visiting the Battery is a must during 3 days in Charleston. The Battery is most well-known as the historic seawall that protected Charleston during the Civil War. It is now a popular elevated walking path right along the river. You can even see Fort Sumter from The Battery which is where the first shots of the Civil War happened! 

Additionally, if you love viewing multi-million dollar homes, these classic Charlestonian homes are one of a kind. As you continue walking along the Battery, don’t forget to stop by White Point Garden.

This area offers 5.7 acres of large oak trees, shading benches, and monuments across from the river. Fun fact: this is also a popular place where people get married.

The Battery in Charleston South Carolina

Bonus Alleys to Stroll Down in Charleston – Longitude Alley & Stolls Alley

Charleston is full of charming alleys. If you still have time left in your day and you’d like to add two more alleys, I would recommend adding both Stolls Alley and Longitude Alley. Stolls Alley is right by the battery and is lined with red brick.

Longitude was my favorite alley we explored. It is a wide cobblestone alley that brings you through the back of some beautiful homes.

Longitude Alley in Charleston weekend - greenery on either side with coblestones

Angel Oak

This particular attraction will require a car. If seeing one of the oldest oak trees interests you, I would recommend the 25-minute drive, although, if it wasn’t for wanting to take a photo, I probably could have skipped this activity.

Don’t get me wrong, the tree is absolutely beautiful, even with tons of tourists completely disregarding the rules to not climb the tree. On top of that, it is free to visit.

The rules are a little strict. No blankets, no professional camera posed photos, tripods, props, drinks, and food. Pets are allowed but need to stay by the benches.

Hours: Monday – Saturday 9 AM – 5 PM (they stop letting more people in around 4:30 PM) Sunday 1 PM – 5 PM

Address: 3688 Angel Oak Rd, Johns Island, SC 29455

Top view of the Angel Oak tree in charleston is one of the coolest things to do

Day 3: Folly Beach, Cypress Gardens, Fort Sumter National Monument, Another Plantation

On day 3 of our Charleston itinerary, I want to give you some options to choose from. This is because, while we can cover a lot with 3 days in Charleston, we can’t see it all! So, on day 3, I recommend at least one of the below:

  • Enjoying a beach day
  • Taking a day trip to Fort Sumter
  • Visiting Cypress Gardens
  • Seeing another plantation. 

Depending on your travel style, you may be able to see two of these attractions.

Folly Beach – Perfect Day Trip from Charleston

If you are visiting Charleston during the summer, you may want to cool down at the beach. Located less than 30 minutes away, Folly Beach is one of the most popular beaches outside the city.

Enjoy 6 miles of pristine coastline full of tons of activities. From paddle boarding and surfing to walking the pier and fishing, this beach town has something for everyone. You may even see dolphins during your visit!

For food and drinks, check out some of the top-rated places, including Snapper Jacks, The Crab Shack, and Loggerhead’s Beach Grill. 

Already been to Folly Beach? You can also enjoy some beach time at the Isle of Palms, Sullivan’s Island, and Kiawah Island.

Cypress Gardens

Cypress Gardens became extremely popular after the movie The Notebook. This is the famous filming location where Noah and Allie row in the boat. The Cypress Gardens have been open since 1932. This is about a 45-minute drive northwest, but a cool experience. Walk or row along with the giant cypress trees as you make it through the swamp. 

You may even see some alligators. The gardens are also pet-friendly (November-February), although I don’t believe pets are allowed in the row boats.

Admission: $10 USD per person. Find tickets here.

Address: 3030 Cypress Gardens Rd, Moncks Corner, SC 29461

Fort Sumter National Monument

A day trip to Fort Sumter National Monument is perfect for history buffs. After all, these ruins are where the start of the Civil War happened. Take a ferry ride over to explore the brick fortress and take a deep dive into American History. 

Did you know the attack on Fort Sumter was the longest Seige in American History? It takes about 30 minutes to get to the Fort by boat and the area is run by the National Park Service. Because of this, Rangers are there to provide additional insight into this historical landmark. 

To get to Fort Sumter, you can catch the ferry at two different locations. The primary departure point is the Fort Sumter Visitor Education Center located at 340 Concord Street, Charleston. Boats also depart from Patriots Point, at 40 Patriots Point Boulevard, Mount Pleasant.

The ferry admission is $32 USD.

Visit a Charleston Plantation

Last but not least, you can head to another plantation. Other popular plantations to visit in the area are Magnolia Plantation and Gardens, Middleton Place, and Drayton Hall. 

Magnolia Plantation is known for having exquisite gardens. The gardens were even named by Travel and Leisure as one of America’s most beautiful Gardens. They also offer information on the dark side of the Plantation. Here is a Magnolia Plantation Tour.

Another popular plantation to visit is Middleton Plantation. This plantation offers 65 acres of formal landscaped gardens, a look at plantation life with exhibits, guided tours, and the Stableyards. Tickets can be found here.

Drayton Hall Plantation is an 18th-century mansion located right on the Ashley River. Admission includes an audio guide of the property, so make sure to bring headphones. You can explore this massive property and gardens that cover 125 acres.


Getting Around Charleston

As mentioned throughout this Charleston itinerary, driving and walking are completely doable. If you stay around the Downtown area in Charleston, you really don’t need a car at all. However, Charleston is a popular road-trip destination, so if you have a car, you will find parking.

Staying in Mt. Pleasant can be helpful for free parking at your accommodation. Besides driving and walking, you also have the option of uber or even taking a Trolley Tour.

Charleston Iron gates and colorful homes

Best Way to Get To Charleston

Charleston is a great city to road trip if you live on the East Coast. It is less than a six-hour drive from major cities, including Raleigh, Atlanta, Savannah, Charlotte, and Orlando. 

Charleston also has an International Airport (CHS) with direct flights coming in from Washington DC, Chicago, Orlando, Denver, Seattle, Dallas, Los Angeles, and more.

Airlines include Jetblue, United, Delta, Southwest, Alaska, Frontier, and American Airlines.


Where to Eat in Charleston

Charleston is known as a foodie’s paradise, so this itinerary had to have its own food section! Here are some of the best places to eat and drink in Charleston, SC.

  • Poogan’s Porch – Southern Fare
  • Hank’s Seafood Restaurant
  • Church and Union Charleston – American
  • Fleet Landing Restaurant & Bar – Southern Seafood
  • Husk – Southern

Additionally, foods that Charleston is known for include their BBQ, Hush Puppies, Shrimp and Grits, Cornbread, Fried Green Tomatoes, and Okra Soup. If food is really your jam, you may even consider a Charleston food tour!


When is a Good Time to Visit Charleston

Because of Charleston’s geographical location, the “best time” to visit is Spring and Fall. Summer is also popular, although, Charleston’s summers can be brutally hot. If you plan to spend a lot of time by the beach, however, summertime might be perfect for you. 

Spring will likely be the busiest time of the 3 seasons. We visited during the fall and the weather was lovely and the crowds weren’t bad at all!

n adgers wharf photo spot in Charleston. Woman in blue dress

Where to Stay in Charleston

To be closest to the action, staying in the downtown Charleston area is best. However, if you have a car and want to save a little, staying in Mt. Pleasant is completely fine! If you do not have a car, I would suggest downtown for sure. 

  • The Vendue – Lovely boutique hotel centrally located in the French Quarter, pet-friendly, and nice rooftop bar.
  • Hotel Emeline – Luxury hotel centrally located. 
  • Harbourview Inn – One of the only hotels on the water.
  • Cambria Hotel Mount Pleasant – Charleston – A little further from downtown at a much better price.
  • Staybridge Suites – Mount Pleasant – Large rooms, better for families, and affordable pricing.
  • Francis Marion Hotel – Located on King Street (downtown), if you want more of a city vibe, but a little further from the historic landmarks.

Weekend in Charleston Itinerary – Wrap-up

This concludes my jam-packed Charleston itinerary! I hope this helps you plan an epic trip to the low country. 

If you have any questions about these 3 days in Charleston, or feel like I missed something, let me know in the comments below.

If you found this Charleston Itinerary helpful, I’d appreciate it if you could share it below!

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Samantha Oppenheimer

Samantha Oppenheimer (Sam Opp) quit her corporate marketing job in 2018 to travel the world and become a travel writer, blogger and content creator. She loves experiencing authentic travel experiences, photography, and nature. Sam shares helpful travel itineraries, travel tips, budget tips, and travel advice from her personal experiences. You can also find Sam's words featured in large publications including Mirror, Thrillist, and Well + Good.

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