A First Timer’s Guide to 3 Days in Charleston

Are you planning a trip to Charleston, South Carolina? We just got back from a long weekend there and we loved it so much. It was our first time and we didn’t know what to expect so I’ll explain everything you need to know in this post.

I knew Charleston was going to be amazing, but honestly, it was WAY more beautiful than I could’ve ever imagined! The Southern charm oozed from every corner and even though I just returned home I’m already itching to go back.

How’d we get to Charleston?

Since we were planning on only visiting Charleston (not driving all over the state like we usually do) we decided to fly from Nashville. It was a little over an hour with a direct flight and both airports are very easy to navigate!

When did we go?

We went in mid-May and the weather was great, it rained a little but overall it wasn’t too hot or cold. The days were warm and the nights were cool but not too cold where I needed a big jacket. A few of the people we spoke with told us we lucked out with the weather. Apparently, it can get very hot and muggy in the warmer months. The ideal time to visit is Spring and Fall.

The Vendue Hotel in Charleston, South Carolina
Our cute hotel room

Day 1

Fly to Charleston & Check into the Hotel

We got in around midday Thursday and took a cab to the hotel. Ubers were $45 and the cab was $35 so be sure to price check when you land.

We checked into our hotel, The Vendue, and fortunately, our room was ready early. The hotel is really beautiful and unique! It has lots of bright colors, great art, and is in the perfect location. It is very close to the water and close to all of the restaurants, and King Street. The staff was very accommodating- they told us that they drop off pastries every morning on our doorstep, have wine (and sometimes cocktails) between 4-5 PM, and at night they provide milk and cookies (how cute, right?). The bed was comfortable and the rooftop bar has amazing views of downtown/ the water. We loved staying there.

Since it was pouring rain we couldn’t really explore yet, so we ended up walking across the street to Pearlz for lunch. Apparently, this is a Charleston staple, but to be honest, the food was just ok. I wouldn’t recommend it compared to some of the other amazing places we went. After lunch, it was still pouring so we just went back to our hotel and settled in. We took a nap and then got ready for dinner.

The Carpaccio at SNOB in Charleston, South Carolina
This was the Carpaccio at SNOB- It was yummy but salty

We booked a reservation for SNOB (Slightly North of Broad and showed up an hour early by accident. SNOB was able to seat us early and we had a great time. They were very accommodating and brought us champagne and dessert because Steve told them it was our anniversary. 

After dinner, we wandered a few blocks over to King Street and strolled around the vacant streets until midnight. It was so much fun. We walked over the famous Pineapple Fountain at night and sat on a bench overlooking the water.

The Pineapple Fountain in Charleston at night
The Pineapple Fountain in Charleston at night

Day 2

We booked a horse carriage tour for day 2 and I was SO excited. We walked around the city for breakfast beforehand. We went to Clerks Coffee House in the Emeline Hotel and Steve had the best Chai latte we’ve ever tasted! We also ordered a bagel, which was surprisingly good, then we walked over to the tour. 

The Horse Carriage tour was great! They start by explaining how they care for the horses, where the horses come from, and made sure to stress that they are very well loved. My one tip for the tour is to sit near the front. They had us in the back row and I couldn’t hear half of it. But regardless, riding a carriage around Charleston is very enjoyable and Steve was able to decipher what the tour guide was saying so I got the main gist of what was going on. I’m glad we did this early in the day because we passed so many places we knew we wanted to revisit and really got a feel for the Historic District of the city.

Horse Carriage tour in Charleston
Be sure to sit up front during the Horse carriage tour so you can hear everything

After the tour, we wandered to the Charleston City Market and I gotta say, it’s overhyped. A lot of cheap souvenirs that look like they’re from China. There were a few cute booths but if you’re pressed for time I’d skip this attraction.

Next, we headed to King Street and went to lunch at The Watch Rooftop Bar. It has an amazing view of the city and was such a pleasant experience. After lunch, we continued to shop on King Street. There are clothing stores, antique stores, art galleries, and great souvenir shops.

What to do in Charleston, South Carolina
Such a great time in Charleston!

King Street is so long! We could have easily spent more than one day shopping. If I wasn’t with Steve I probably would have. This would be the perfect place to go on a girls trip or bachelorette party. I’ve truly never seen so many clothes I liked all in one place. 

That evening we took a pedicab to dinner and it was a great way to see the city. We thought it was going to be $15 total, which was the same price as the Uber to go 1.1 miles, but it ended up being $15 per person. Whoops. I highly recommend you do it though, it was really fun.

We went to dinner at Indaco, an Italian restaurant. It was delicious! Then we wandered down the other end of King Street where all of the nightclubs are. This is where the party is if you’re into that! It was fun to see all of the people out and about. Once we crossed into the more subdued side of King Street it was a peaceful walk back to the hotel.

Rainbow Row in Charleston
This is Rainbow Row

Day 3

We borrowed the bikes from our hotel and rode down by the water and The Battery. We rode by the houses on Rainbow Row and had lunch at Queens Street Grocery. This was my favorite meal in Charleston! It’s this little hole in the wall in the middle of a neighborhood of gorgeous homes.

Queen Street Grocery, Charleston
We loved this little deli!

If you go be sure to order the Tenacious Turkey. It has turkey, brie, green apple, sprouts, honey basil aioli on ciabatta… YUM. I haven’t had a sandwich that good in a long time. Steve got a breakfast Crepe and it was eh… But the sandwich? A must.

The Tenacious Turkey at Queen Street Grocery
The yummiest sandwich- The Tenacious Turkey

We parked our bikes and relaxed while looking at the water along the Peninsula in the Waterfront Park. It’s such a beautiful and peaceful area.

Biking around charleston, south carolina

Our final stop for the day was Shems Creek. We took an Uber and wow it is stunning! There are restaurants on the water and you can walk along this long dock and enjoy the scenery. 

The prettiest houses on Shems Creek

A few people recommended Saltwater Cowboy for dinner and drinks to watch the sunset. I’m not sure if it was just this specific weekend or if it’s always like this but it was more like a day club than a relaxing dinner. There was a DJ that also played the saxophone, lots of drunk college kids, but also lots of families- it was a very eclectic group. The view was amazing and the food was decent. After dinner, we walked the dock and snapped some great photos.

Lauren and Steve Erro on Shems Creek
This photo turned out so well!

When we got back into town we went to our hotel’s rooftop bar to watch the sunset. It was really fun up there! When the sun went down we went on the hunt for dessert. We stumbled upon this cute little Key Lime Pie place (Kermits Key Lime Pie). We got a slice of pie and people watched for the rest of the night.

**The best tripod!

If you want to take great photos while you travel, This tripod is AMAZING! It is collapsible so it can easily fit in your day bag. It stands on its own and expands to reach 60 inches! I love that it has a Bluetooth remote control (that attaches to the tripod for safekeeping) so you can set up your phone, walk away, and get a great pic. It can take vertical or horizontal photos. Every time we used this so many tourists would come up to us and ask about it. It takes all of our photos of us without us having to ask strangers for help.

Day 4

Our last day was Mother’s Day and our flight left at 1 PM so we had some time to have a yummy breakfast and explore. Most of the places had long waits and required reservations so we ended up eating at this little diner called Sweetwater Cafe. It was good! We walked around a bit more, sat on the swing benches on the dock, then took an Uber to the airport. The airport is small and very efficient. I’m impressed!

Shems Creek
This is from Shems Creek

Charleston FAQ:

How should you dress in Charleston?

This is the city where you can dress your best! Everyone was very well dressed and I loved it! The women wore dresses and the men wore polos or button-downs. Flat shoes, sneakers, and sandals were fine for women. Men wore loafers and sneakers. Even the kids looked cute in their polos and dresses. We saw a lot of families matching. Lots of bright colors, girly frilly dresses, and preppy outfits. If you need ideas on where to shop I have a post with the best feminine stores HERE. These sneakers are a must for travel- they’re very lightweight and they have supportive soles.

Is Charleston walkable?

Yes! Well, at least the downtown part is. We walked over 10,000 steps each day just exploring the city. The sidewalks are treacherous and there are some cobblestone streets so I recommend wearing sneakers or supportive sandals. I brought a pair of heels and unless I Ubered to the front door I don’t think I would have survived in them. 

King Street, Charleston on a Saturday
King Street, Charleston on a Saturday

Should you bring a car to Charleston?

There seemed to be a decent amount of parking around Charleston. Lots of parking meters and paid parking lots are available, and of course hotels have Valet options. But the city is pretty small so if you’re ok walking you’re probably better off doing that.

Uber & Lyfts were pretty expensive there. The city is tiny and to get anywhere it costs a lot. There were long waits for Uber & Lyft as well. It could be because it was graduation weekend and Mother’s Day though. I’m not sure what the norm is.

Charleston, South Carolina

Is 3 Days in Charleston Enough?

Yes and no. If you’re looking for a relaxing getaway 3 days is plenty! If you’re trying to see all of the historical sites, plantations, etc. You probably need more time!

What Else Should You Do When You Visit Charleston?

I asked my Instagram followers if they had any recommendations and this is what they said:


Joesphs for breakfast

Halls chophouse for dinner or Sunday gospel brunch

High Cotton for brunch

Fleet landing for lunch


Taco boy

Oak Steakhouse

Church & Union

Chez Nous


Leon’s Oyster Bar

The Agnolotti

Tavern and Table

O Ku


Camelias Champagne Room

Magnolias for dinner

Kaminsky is a yummy dessert place

The sunset from The Vendue in Charleston
The sunset from The Vendue in Charleston

Other activities to do while in Charleston:

Visit the nearby plantations

Carriage ghost tour

Guided walking tour

Folly island

Mount Pleasant

Food & Wine tours

Fort Sumpter

Take a Segway tour

I hope you have an amazing trip to Charleston! You’re going to love it!

The cutest candle store in Charleston- on King Street
The cutest candle store in Charleston- on King Street

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