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The Ultimate 4-Day Travel Itinerary For Charleston South Carolina

Planning a trip to Charleston, South Carolina? I’ve got you covered!

From learning about the astounding history of this lively city that has its many notorious "hauntings" to savoring the delectable Southern-style food, Charleston has much to offer. In my Ultimate 4-Day Travel Itinerary For Charleston, South Carolina, I will provide guided tips on the ins and outs of experiencing this historic Southern city for the first time. With a range of activities like learning about Charleston’s history at the Charleston Museum or checking out the nightlife of this lively historic city, I’m going to show you how my first time in this city went, leaving 100% honest reviews of my 4-day birthday trip!

Important Tips

  • Download the OpenTable app for reservations everywhere in Charleston (highly recommended)

  • Without this app, you won’t be able to make a reservation at most spots in Charleston (learned this the hard way). And trust me, you’re going to want to make reservations if you’re visiting on the weekend!

  • Uber/Lyft

  • For making quick drips to downtown Charleston and back to your Airbnb, especially if you’re there for the nightlife!

Outfit Recommendations

Rainbow Row Outfit

Night Life Outift

Day One

Breakfast At The Daily

The Daily is a hip coffeehouse serving Stumptown brews while supporting local businesses like produce and other intriguing items like sustainable straws. At this inspiring coffee shop, only the highest quality ingredients are used to create healthy and delicious items such as juices, pastries, smoothies, fresh bread, and more!

My friend and I stopped here as soon as we arrived in Charleston, South Carolina, for a much-needed refresher. There was a bit of a wait, about 20 minutes or so. For obvious reasons, The Daily is a popular spot for breakfast, brunch, lunch, and everything in between, which we soon found out after receiving our delicious meal!

I ordered:

  • The Power Protein Smoothie

  • Vegan Vanilla Protein Powder, Banana, Almond Butter, Medjool Dates, & Chia Seeds

  • The Avocado Toast

  • Za’atar, EVOO, & Sourdough

  • **The bread is grilled with butter, but you can inform them when you order to prepare it vegan!

All in all our meal was delicious and worth the wait. We perused the fun little store they had indoors, then ended up finding a seat on the patio. The Daily is pet-friendly, so there were plenty of curious and adorable puppers with their owners on the patio, which I for sure didn’t mind!

Tour The Charleston Museum

One of the oldest museums in the whole United States, the Charleston Museum was another one of the unplanned stops we made during our trip to Charleston.

My cousin's flight had been delayed about four hours, so my friend and I had plenty of time to kill. After stopping for breakfast at The Daily, we parked at the Charleston Museum and made our way inside---it’s much larger inside than you may initially think! The large collection of historic artifacts, decorative arts, and natural history was incredibly inspiring to read and learn about.

Right across the street is the Nathanial Russel House, which we ended up exploring too. When paying for your ticket for admission into the museum, there’s an add-on option to explore two historic houses---one of them was the Nathanial Russel House and the other was a driving distance away that we weren’t interested in taking after the long trip it took to arrive in Charleston.

Tour The Nathaniel Russell House

The Nathaniel Russell House is a skip across the street from the Charleston Museum. This historic house was built in 1808 by Nathaniel Russell, a wealthy merchant and slave trader. Officially recognized as one of America’s most important neoclassical houses, the Nathaniel Russell House was designated as a National Historic Landmark in 1973.

Through the Charleston Museum, you can buy an admission ticket for the guided tour of the Nathaniel Russell House. Without the very informational tour guide, we would have been bereft of a load of intriguing information---like how a Princess once owned the house!

Rest Stop At Uncork

A classy and fun self-serve wine bar in Charleston, Uncork serves top-notch wines from all over the world, including my personal---and only---favorite, Sangue di Giuda. Explore different wines, sit with friends in the pleasingly aesthetic setting, and pair your wine with a charcuterie board made with fresh locally-sourced ingredients.

Uncork was a pleasant surprise on day one of visiting Charleston. My friend and I had driven up (at a horrifically early hour) from Florida to pick up my cousins from the airport in Charleston. Unfortunately, their flight was delayed by around 4 hours so my friend and I had to kill some time. After stopping at The Daily for breakfast, we strolled through The Charleston Museum and the Nathanial Russell House. Building up an appetite, we headed over to the famous Charleston spot, King Street, and decided to stop in to check out Uncork.

We had a great time sitting to chat in the glorious appeal of Uncork with wine and snacks in hand. Since our visit to Uncork in August 2021, we have yet to forget this unforgettable spot. If you’re looking to sit and relax, Uncork is the perfect place to simmer down with wine in hand and good company to chat with.

Dinner At O-ku

A trendy Japanese eatery and lounge located on King Street, O-ku deserves all the hype it’s been receiving. The exposed brick and high ceilings make for an astoundingly aesthetically pleasing spot for dinner---plus pictures for the ‘gram!

When I say I smashed the House Salad---the classic carrot and ginger vinaigrette pairing that hits so good every time---and the Eat Your Veggies Roll---mixed greens, pickled daikon, cucumber, and carrot---I mean I devoured that freshly delectable food like I was Patrick Star vacuuming food into his mouth.

We stopped at O-ku our first night in Charleston, South Carolina before we spent the night out on King Street. To start the night off, we went to Republic Garden and Lounge--before then quickly transferring over to a less crowded bar spot, King Street Dispensary.

A Night Out At Republic Garden & Lounge

A very popular nightclub on King Street, Republic Garden & Lounge slays a sophisticated aesthetically-pleasing setting along with innovative cocktails and trendy music.

Unfortunately…it was packed. I’m talking about sharing air with other people packed. Shoving past others like it was a heckin’ mosh pit packed!

It got exhausting not having any personal space and there was no chance we could get a drink at the bar without having to wait 20-30 minutes to finally get a chance to sidle in between people to reach the bar…

So we headed over to King Street Dispensary which was much less crowded and actually enjoyable to hang out at.

Hang Out At King Street Dispensary

A typical hole-in-the-wall sports bar, King Street Dispensary serves a wide selection of local beers and liquors. This is where I had my first Gatorade shot...still indecisive if I was a fan of it or not.

Compared to Republic Garden & Lounge, King Street Dispensary was a complete 180-degree turn in setting, aesthetic, and vibe. My group and I had a blast there, all of us able to take a breath of fresh air (that wasn’t mingled with others) and vibe, chat, and dance to our hearts' content.

I recommend coming here if you want to get away from the hustle and bustle of the more popular nightclub and hangout spots off King Street!

Day Two

Brunch At The Rarebit

The Rarebit is a bustling eatery and cocktail bar serving American comfort food classics in a mid-century aesthetic. For all the breakfast lovers, you’re going to L-O-V-E love The Rarebit---they serve breakfast all day! From huevos rancheros to chicken & waffles and my two all-time favorite breakfast options---fresh avocado toast and crispy breakfast potatoes!

In all honesty, our original plan wasn’t to go to The Rarebit but to another breakfast join off King Street. Waiting for everyone to wake up and get ready to skedaddle when you have a large group of people is probably the most frustrating aspect of dealing with hunger pangs first thing in the morning LOL. By the time everyone was ready to gorge down some food, it was noon…so brunch instead of breakfast.

I ended up having to cancel our original reservation and call in ahead to Rarebit. No surprise there, but there was a 20-30 minute wait (on a Saturday) so we ended up walking around King Street for a little while as we waited for our seats. Then…we ended up getting squished into a teeny-tiny booth…which was not fun. Getting elbowed as you’re trying to smash avocado toast in your mouth is not the cleanest experience I tell you…

Like our experience at Mesu, I would highly recommend not having a large party if you decide to grab breakfast or brunch at The Rarebit. They really don’t have comfortable seating to allow for personal space in a large group. For a small group or for couples, The Rarebit would be a comfortable setting to enjoy breakfast with loved ones over fresh savory and sweet breakfast options.

Walk & Shop Down King Street

The most famous street in Charleston, the Charleston Historic District of King Street is a vibrant and eclectic downtown stretch stacked with options ranging from antiques, fashion, home decor, decadent food, and more. With a history of 300 years, King Street is a bustling historically and architecturally significant spot that was named after King Charles ll of England.

If you’re looking to see what Charleston, South Carolina has to offer, it’s going to be impossible to miss out on King Street. The epitome of Southern history and charm, walking down the length of King Street will pave a path to many different shops and experiences like Rainbow Row and The Historic Charleston City Market. Stop in for a quick lunch and buy some souvenirs as you embark on an eventful journey down the popular historic King Street.

Shop At The Historic Charleston City Market

The Historic Charleston City Market is a historic market complex located in downtown Charleston off of King Street. First established in the 1790s, this market stretches on for four city blocks all the way to the Market Hall, a Greek Revival landmark built in 1841 that offers Civil War history tours.

It’s at this market that visitors can shop for all types of items like Gullah sweetgrass baskets, jewelry, fresh produce, and freshly baked goods. The Historic Charleston City Market is a popular socialization point for locals and tourists alike!

**If you’re looking to get your steps in, you can walk the length of King Street to the Historic Charleston City Market and then stop over to snap some pictures at Rainbow Row.

Snap Pics At Rainbow Row

Rainbow Row refers to thirteen pastel-colored historic houses that have become widely popular for fantastic aesthetically-pleasing pictures like the one I took above!

**I highly recommend planning an outfit for this point in your trip (if you want to, of course!). I was super pleased with the results of my photos and got a cheap outfit off of Amazon that I will link in this article!

Snack At Babas On Cannon

A cute European-inspired cafe serving coffee, cocktail, and light bites, Babas On Cannon was a fun quick stop for a much-needed snack after walking the long and extensive streets of King Street to Rainbow Row and the Charleston City Market.

I was the only one---lone wolf here!---that desired a quick snack. I was also in desperate need of some espresso of some sort. Walking really does take a toll on you in the sun!

I ordered the Peanut Mocha (Iced) drink:

  • Espresso

  • Babas Peanut Milk

  • Chocolate

It was surprisingly delicious and for all the peanut lovers, I would highly recommend trying out this sweet nutty espresso drink!

Dinner At Mesu

A trendy Asian-Mexican fusion restaurant, Mesu is scattered with colorful displays of street art. This urban restaurant serves tequila infusions and sake sangrias, only two of the creative fusion drinks that are a part of their extensive cocktail list.

In all honesty, Mesu was my least favorite restaurant that we visited during our trip to Charleston. The veggie tacos were delicious and the seasonings on the tortilla chips were crazy delicious---and I have yet to see any other restaurant mimic the perfect seasoning combination---but the dessert order of churros was stale, and our server was infrequent with his attention to our table (I’m not a Karen I promise LOL), and we were seated at an almost amusingly long extensive table---like I’m talking King Arthur and The Round Table big--- that made it impossible to chat with others in our group over the loud music and hefty distance between the others.

Personally, I would not go back to Mesu, but a smaller party (we had 7 of us) may be more suited when visiting this Asian-Mexican fusion spot.

Day Three

Breakfast At Virginia’s On King