Must See Sights In Charleston That You Shouldn’t Miss
Road Trips,  Solo Female Travel,  Travel

Must See Sights In Charleston, That You Shouldn’t Miss


Spending 24-48 hours in a new city doesn’t need to be daunting. Sometimes, the best thing to do is: see the highlights. If you’re headed to South Carolina though, I’ve got you covered! Here are my Must See Sights In Charleston, That You Shouldn’t Miss, post!

P.S. If you can’t see them all, promise yourself to go back someday.


Philadelphia Alley
Famous Philadelphia Alley
Philadelphia Alley
Philadelphia Alley
Philadelphia Alley
Philadelphia Alley Plaque
Charleston SC
Charleston’s Georgian Style Home

Must See Sights In Charleston That You Shouldn’t Miss

Historical Charleston is as charming and colorful as you’ve read. If you’ve been following me, it was a stop on my Solo Southern Road Trip. I wasn’t expecting to learn so much about the city, but that’s a part of its appeal to travelers.

Alright, keeping this short and sweet for y’all. I know you’re just looking for the Must-Sees!

Historic Charleston City Market

This Market is, in fact, incredibly historical. It’s been a market since the 1790s and, for America, that’s old. You can read all about its origins here.

Today, the market is 4 blocks and stalls range from art, ornaments, and candied pecans (picked up 3 bags of them). It’s a great place to pick up souvenirs and where I bought all my postcards and cajun spices.

Philadelphia Alley

One of the most famous Alley’s in America and not a lot of people know why. You can read about it here.

In short: There were a lot of gentleman duels in that alleyway. It’s full of bullet holes, survived a terrible earthquake and a fire.

It’s also instagram famous so you’ve surely seen it on your feed.

St. Michael’s Churchyard

There are TWO American constitution signers buried in this churchyard. It’s across the street from St. Michael’s Episcopal Church, which President George Washington attended service during his visit to Charleston in 1791. Robert E Lee also attended a service.

It’s a historic landmark. It was originally built by the church of England but turned during the American Revolution.

It’s beautiful and in almost every photograph, drawing, and postcard in Charleston. It’s on the Four Corners of Law and super fun to see in real life.

Rainbow Row

There is no way this can be a surprise. Bay St is one of the most famous streets in America!

These beautiful, prestigious, and colorful Georgian-style homes were in the poorer area of the city into the 1920s. The short distances to the pier and port attracted a lot of sailors, booze, and trouble. You can read about it here.

It’s definitely iconic. Make no mistake, despite its popularity on instagram, it’s actually worth the visit. I wish you could explore the interiors because many have been renovated to the times. They are residential homes so the only way you’ll catch a glimpse is in a magazine or if you know an owner (or Redfin).


Rainbow Row
Rainbow Row on Day Two
John Ruthledge Grave
John Ruthledge Grave St Michael’s graveyard
Charleston Sunset
Sunset at the Citrus Lounge
Historic French Quarter Alleyway

Historic French Quarter

The French Quarter is old Charleston. It’s darling. I walked these streets and alleys for hours just looking at the houses, graveyards, and church towers.

If you can, I highly recommend booking a walking tour of the area. They will give you the run-down on everything you’re passing by and can confirm that the repurposed canons are walkaway dividers. 😅

Tours I recommend:

Waterfront Parks

I’m sure many of you are expecting to see Charleston’s famous Pineapple Fountain on this list. To be honest with you… it’s just a fountain. Sure, it’s all over IG. It’s a great photo op, but the port and piers in Charleston are breathtaking. Especially at sunrise and set.

E Battery St is lined with Georgian & Federal-style homes and on the other side is a sandy beach waterfront. I also think White Point Garden is underrated.

Southern Comfort Brunch

No joke, Charleston has some of the best comfort food experiences I’ve ever had. Everything was packed full of wonderful spices and… happiness! Haha! Here is what not to miss:


I hope you guys are enjoying my Solo Southern Road Trip series. If you’re new, I traveled from Savannah, Charleston & Asheville on this adventure and it was one of the best self-care journeys I’ve ever had. If you’re looking for more on The South, definitely check out that series.

I feel like I’m missing something so, check back to see if I add on to this list! If you think of something, leave me a comment below.

Happy Traveling, dolls! 💕

Love Alli // On the Trip side Signature

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