My Little Guide to Charleston

Pineapple Fountain

Heading to Charleston was a last minute decision after our planned trip to the Bahamas didn’t end up working out. My best friend, Jana, and I decided we would find a place we could drive to and that neither of us had been to. Don’t ask me how we lived in Savannah for several years without ever making it up to such a beautiful city! I got to check another pink hotel off of my list of must-sees, which I was extremely excited about.

Here’s the list of where we stayed, what we ate, and what we did!


Seen above, we stayed at The Mills House. It was gorgeous! We booked poolside rooms and I’m so glad that we did. Our rooms had our own porch with a gate just steps away from the pool. We spent both our mornings and evenings enjoying the patio. These are the only rooms that have access to an outside area. The rooms inside were pretty generic, nothing super special, but we obviously didn’t spend much time in the room so it wasn’t a big deal. The location of the hotel was PERFECT. Once we figured out the city, we realized we could walk to most places downtown and it’s just a block away from shopping on King Street. If we ever go back to Charleston, I would definitely love to stay at Hotel Bennett (more on that later).


Took a day trip to Folly Beach.

  • Started our day there with lunch at Loggerhead’s, which was recommended to me. Great food and an awesome rooftop/outside atmosphere!
  • We were going to park a bit further out from the pier, but parking wasn’t great – especially now because they changed their parking rules due to Covid.
  • Ended up posting up right next to the pier so we could grab some shade since we didn’t have an umbrella. So glad we did this!
  • It was CROWDED. We kept moving ourselves away from people as they got closer. We did have so much fun people-watching, though!
  • Wish we could have gone to Isle of Palms or Sullivan’s Island instead. Next time!

We took a few rickshaw rides around the city to see all that we could. This was actually really fun – the drivers know a lot about the city and it was like having a personal tour guide.

We checked out Rainbow Row and the Pineapple Fountain. Definite Charleston must-sees!

We walked the Historic Charleston City Market twice. This was a fun spot to find some neat things to bring back to the boys.


  • Leon’s Oyster Shop – I read that this was a place we HAD to go, so we had dinner here the first night. I wasn’t super impressed, but it was good!
  • Basic Kitchen – We had brunch here on our first full day. The cutest place ever. All the food is farm to table, so if that’s your thing, check this place out!
  • Fleet Landing – This is the only restaurant on the water in the city. We stopped in for a drink one day while walking around and then came back for lunch a few days later. Only bad thing about this place now is that they are doing ALL the construction outside so it’s not as easy to get to and a tad noisy sitting on the deck.
  • 5 Church – I would say this was my favorite dinner stop that we made. This place is GORGEOUS and the food was delicious. They had a maple bourbon goat cheese on their charcuterie board and I haven’t stopped thinking about it since we left.
  • Carmella’s Cafe & Dessert Bar – This place was amazing! You can eat, drink, and get dessert all in once place. We came here one night after dinner for dessert, and ended up back here a few days later for a light lunch and mimosas!
  • Magnolia’s – We stopped here on the night we were just checking out restaurants for appetizers – they have deviled eggs with candied bacon, so I was sold as soon as I read it on the menu.
  • Taco Boy – I also read this was another must-go. I would definitely recommend this place for larger groups. Super fun atmosphere and the tacos were great – just know that on certain days of the week that they only have tacos and not a full Mexican menu.
  • 167 Raw – YES. Go here. I had the lobster roll and Kevin couldn’t get enough of the oysters. They don’t take reservations, but while you wait, they guide you to a vintage wine bar just down the street.
  • Edmund’s Oast – We checked this place out on out last night and loved it. Right now it is only open for outdoor seating, but I wouldn’t have wanted to sit inside anyway.


  • Vintage Lounge – This was our very first place that we went. Always start a vacation with bubbles and charcuterie! They had a super cute back patio with an outdoor bar – most of the seats are covered in case it rains/for shade!
  • Star’s Rooftop
  • Blind Tiger – The oldest bar in Charleston. Doesn’t look like much from the outside but they have an outdoor space that was to die for! This was a tequila stop for us because they made the perfect jalapeño margarita!
  • Doar Bros – Kevin is the one who found this place, just a short distance from our hotel. It. Was. Amazing. A small, navy blue interior with the sweetest, most knowledgable bartender who made wonderful drinks. This is where I had a drink that was rose with sorbet in it!
  • The Watch Rooftop – This is located in the Restoration Hotel. We tried some mid-day adult capri-suns here and they were quite delicious! This would also be a great brunch spot. I loved the atmosphere here.
  • The Rooftop Bar at The Vendue – This was a fun stop for drinks and appetizers. Fun views and plenty of seating.
  • Camellias Champagne Bar – Located inside of Hotel Bennett. Hands down, my absolute favorite place we went in the city. Just everything about it – its pink and beautiful, the fresh flowers, you name it. We decided to celebrate and tried a flight of Veuve Clicquot because, why would you not? The hotel also has a rooftop bar (Fiat Lux) that was perfect, too!
  • Revelry Brewing Co. – This is a brewery not far from Edmund’s Oast. Super fun rooftop, but not very big so be cautious if you’re going at a busy hour. They also sell a few different wines if beer isn’t your thing.

At this time, Charleston is very strict about wearing masks. I thought it would be a pain at first, but it wasn’t all that bad. You have to wear the mask into each restaurant and bar until you’re actively eating or drinking, and if you get up to use the restroom you have to wear it there. I was a little unsure about the rules while walking down the street, so I just always kept mine handy in case I needed to throw it on. Also as of now, no restaurants of bars in the city are allowed to sell alcohol after 11PM.

We had so much fun on this vacation and I’d go back in a heartbeat. A few places were still closed due to Covid – I would have loved to try out Miller’s All Day, it was the only place on my “list” that I made before we went that I didn’t get to check out. But, after being in Charleston, I realize that there was so much more that should have been on my list, so I’ve got those stored for next time!

Have you been to Charleston? Who is coming with me for round two? I can’t wait to go again!