Last March, Dan and I visited Charleston for a baby moon while my mom (aka Super Gran) stayed with our daughter Margot.
Charleston had been high on my list for a long time. We even had plans to do a family trip there when Margot was about a year old, also visiting Savannah, but we went to France that spring and then bought our house, so we decided to save it for another time.
Charleston is one of the few places we can fly to directly from our home airport in Syracuse, but the flights are very limited. We flew down late Friday night and came home super early Monday morning. While the timing was a little tiring, it actually worked really well with leaving Margot for the weekend – we were able to be with her all day Friday and then get home early enough Monday to pick her up from day care. For a three-night trip, we only missed seeing her for two days.
Charleston has been recognized for more than ten years in a row as the best city in the United States by Travel + Leisure’s annual readers’ choice World’s Best Awards. I would be wary to give that title to any one place given how many factors could be considered and what different people are looking for, but it shows how extremely popular the city has become as a place to both visit and relocate to.
With colorful architecture set against charming cobblestone streets accented by picture-perfect window boxes and tucked away, shade-filled alleys, Charleston’s historic district is the perfect place to take a leisurely walk and get acquainted with this port city.
Founded in 1670, it’s also an ideal destination for history buffs. Destinations like the International African American Museum (IAMM) and the Old Slave Mart Museum address the city’s prominent role in slavery, with the IAMM located at Gadsden’s Wharf, the first destination for ~100,000 enslaved people arriving in the United States at the height of the international slave trade.
Add in countless day trip options, nearby beaches, and a world-class culinary scene, and it’s no surprise that Charleston is a sought after destination for transplants and travelers alike.
Keep reading for your self-guided walking tour of Charleston, South Carolina.
Self-Guided Walking Tour of Charleston, South Carolina: The Stats
This walking tour is a loop, so you can start at any point along the route depending on what is most convenient for you.
The distance will vary slightly depending on your exact path and any unexpected detours – Charleston is perfect for an unexpected detour! – but my route here is ~2.5 miles, flat, and wheel-friendly due to being entirely on sidewalks.
A good chunk of the route is in a part of the city where there are no shops to be found – the southern part of the historic district as you head toward The Battery and White Point Garden – so be sure to pack a few snacks and fill up your water bottle before heading out, especially if it’s a hot day.
Another option if your schedule allows – split the walk into two so you can break up your sightseeing a little more. Or, save The Battery and White Point Garden for a separate outing, which will automatically take about half a mile off your route.
Self-Guided Walking Tour of Charleston, South Carolina: The Route
Washington Square | 80 Broad St.
This small but lovely park located behind City Hall has a variety of beautiful touches like gas lanterns, bright flowers, wrought iron fencing, and towering Southern Live Oak trees.
St. Michael’s Alley and Elliott St.
We ended up on this street by chance and it was probably my favorite in the whole city – it was so pretty, quiet, shady, and full of beautiful homes to admire.
It’s not the most direct route to your next stop, but it’s worth it. To get here from Washington Square, walk south along Meeting St. for half a block and turn left onto St. Michael’s Alley.
French Huguenot Church | 136 Church St.
Head north on Church St. to check out this beautiful Gothic Revival church framed by palm trees; the first of many pink buildings you will be able to enjoy on this walk and all around Charleston.
Right across the street from the church is the historic Dock Street Theatre, built as a hotel in 1809 and converted to a theater in 1935 as a Works Progress Administration project. The original Dock Street Theatre, opened in 1736, was in a different location and likely burned down during the city’s Great Fire of 1740, which destroyed much of the city’s French Quarter.
Just around the corner from here is the Old Slave Mart Museum, located at 6 Chalmers Street.
Philadelphia Alley | Just off of Queen St. between Church St. and State St.
Take a few steps down one of Charleston’s many picturesque alleyways on your way toward the waterfront.
Come back out of the alley from the same side you entered and continue east. At the end of the block, keep an eye out for the pink building at the intersection of State Street and Queen Street. This was one of my favorite buildings in the city and the intersection in general is beautiful.
Pineapple Fountain | Waterfront Park
Symbolizing hospitality, you’ll likely see pineapples in different forms throughout your trip to Charleston. Built in 1990, the Pineapple Fountain is one of the city’s most popular attractions. Situated in the center of Waterfront Park, you can also enjoy views of the Charleston Harbor, Ravenel Bridge, and Fort Sumter on nearby Shutes Folly Island. Fort Sumter is famous for being the location of the start of the Civil War in 1861.
Before continuing on your way, head out along the Waterfront Park Pier for more views, and enjoy a break at one of the shaded porch swings along the way.
Rainbow Row | 107 East Bay St. to 83 East Bay St.
After walking along the water for a couple of blocks, turn right at Exchange Street or East Elliott Street to head inland again for Rainbow Row. This stretch of buildings between 107 East Bay Street and 83 East Bay Street is one of the most photographed views of Charleston, especially the pastel trio of pink, purple and green homes at its north end.
Between Rainbow Row and Stoll’s Alley, your next stop, you can stop at the Hazel Parker Playground for a bathroom break and water fountain if needed – hours vary.
Stoll’s Alley | Connects East Bay St. and Church St.
Continue south along East Bay Street until you reach Stoll’s Alley on the right. Enjoy a quiet walk along this narrow, shaded footpath connecting you to Church Street.
The Battery and White Point Garden
Turn left onto Church Street and enjoy more beautiful architecture as you continue to The Battery, the southernmost part of the Charleston Peninsula, marking the confluence of the Cooper and Ashly Rivers and home to historic defensive seawalls dating back to the 1750s.
The Battery is surrounded by grand antebellum homes (referring to buildings constructed before the Civil War) and is also home to White Point Garden, featuring a green space with a gazebo, Civil War cannons, and a handful of monuments referencing points in history including the Revolutionary War, the Civil War, and the tragic sinking of the USS Hobson in 1952.
Over the past ~20 years and rising to a high during Black Lives Matter protests following George Floyd’s murder in 2020, there have been growing calls to remove the park’s Confederate Defenders of Charleston monument along with other Confederate landmarks around the city and region.
54 Meeting St. + 63 Meeting St.
Continue your walk by heading north on Meeting Street.
If you’re visiting during wisteria season – usually mid- to late-March – don’t miss two of the best spots in the city to see these beautiful purple blooms at 54 and 63 Meeting St.
82 Tradd St.
Turn left onto Tradd Street to enjoy more beautiful Charleston homes. Keep an eye out for no. 82, just half a block down on your right. This is another one of the city’s beautiful pink buildings.
John Rutledge House Inn | 116 Broad St.
Continue on and then turn right onto either Orange Street or Legare Street to reach Broad Street. Take a moment to enjoy the John Rutledge House Inn, dating back to 1763, then turn to your right for an iconic view looking east toward Saint Michael’s Church, a classic Charleston streetscape you’ll likely see on city guides and postcards throughout your trip.
The Mills House Hotel | 115 Meeting St.
Another of the city’s iconic pink buildings, and this is a big one! A Charleston landmark for almost two centuries, the hotel has undergone many changes and numerous owners over its 171 years. We enjoyed multiple coffees at the hotel’s Black Door Cafe. Grab a seat outside if you can for some people and horse carriage watching. You can also (respectfully) use the hotel’s bathroom if needed. We love a convenient bathroom break on a walking tour!
Just up the street from here is the Gibbes Museum of Art, something to keep in mind especially on a rainy day. The first floor is free to visit. If you’re visiting during the first full weekend of the month, you can also receive one free ticket by showing your Bank of America credit or debit card with photo ID as part of the Bank of America Museums on Us program.
Bonus: King Street Detour
The Mills House Hotel is almost directly across the street from Washington Square, so if you stop here you’ll be right back where you stayed.
If you’re ready for another detour, continue west from the hotel along Queen Street to reach King Street, the city’s main thoroughfare. You’ll come out right by Buxton Books, a bookstore that also offers a variety of themed walking tours.
Right across the street from Buxton Books is the Gateway Walk, leading to pretty gardens and an old cemetery at the Unitarian Churchyard.
Charleston is known for being a haunted city and offers a variety of ghost tours (including some right from Buxton Books), if you’re into that sort of thing!
Apart from this quick preview, King Street deserves a separate walk in and of itself if you have the time. Enjoy shops, restaurants, bars and other city landmarks including Hotel Bennett (step inside for a sweet treat at La Pâtisserie) and the American Theater (which you may recognize from The Notebook – if you’re a bird I’m a bird). I was actually surprised to learn Hotel Bennett was built less than ten years ago. Its construction was inspired by Charleston’s historic architecture and it was designed to look like a building from the 1700s.
It’s also a quick detour from King Street to another of our favorite spots in the city, The Cistern at the College of Charleston (I warned you about the detour possibilities, and I meant it!).
Other Charleston Faves
We managed to squeeze a lot into our short visit to Charleston (as usual, I may have overplanned and pushed us a little too much, especially for a baby moon). Some of our other favorite things were:
- Coffee at Bad Bunnies
- Brunch at 82 Queen
- Dinner at Lewis BBQ
- Breakfast at Island Provisions Downtown CHS – their ‘The Boss’ brekkie sandwich was so good
- Apps and drinks at Basic Kitchen
- Walking through Hampton Park
- Sunday stroll along King St.
I hope this self-guided walking tour is a helpful starting point for your time in Charleston. There is so much to see in the city and surrounding area. Whether you travel for the beach, cuisine, cafes, museums, architecture, history, nature – the list goes on! – I bet you will find something you love.
Use this map to guide your walk.
Have you been to Charleston before? What was your favorite part? If you haven’t been yet, is it on your list? Let me know in the Comments!
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1 Comment
Prabik
February 25, 2025 at 5:35 amThanks for sharing your experience in Charleston! Your walking tour sounds like a perfect way to explore the city’s history and charm. I especially enjoyed your descriptions of Rainbow Row and The Battery. After reading this, it reminded me of my own strolls through historic districts—there’s something special about discovering hidden alleys and beautiful architecture.