72 Hours in Charleston

Jess Ann Kirby visits Rainbow Roe in Charleston South Carolina
Craig and I had such a wonderful visit to Charleston last week with JetBlue Vacations. When Charleston came up as an option in our partnership to experience one of their vacation destinations it was a no-brainer. Having visited the city for the first time during my girls trip last fall, I was really excited to go back with Craig. It’s such a quick and easy flight, about 2 hours from Boston, just enough time for me to post an Instagram and watch a movie, haha! Seriously though that JetBlue free WIFI and personal TV situation is THE BEST. The perfect long weekend or mid-week escape, Charleston is a great getaway, particularly as the weather gets colder. If you’re headed south, here are some of my favorite things to do and see, and of course where to eat, in Charleston.

*For those of you looking for outfit details I’ve linked to everything I’m wearing at the very bottom of the post!

Jess Ann Kirby shares the architecture of Charleston South Carolina in a 72 hour long weekend trip
Jess Ann Kirby wears a blazer and skinny jeans on Rainbow Row in Charleston South Carolina

What to Do & See

If you only do one thing in Charleston, make sure it’s somewhere South of Broad. The charming historic neighborhood is so fun to explore. Walk around and get lost on the cobblestone streets and hidden alleyways. We spent hours discovering little side streets and admiring beautiful aging stucco homes and historic architecture. The city has done a great job of placing informational signs throughout so you can read about the history of the homes and buildings. It’s also a great city to explore by bike, you can rent them or most hotels have them available for guests. We didn’t get the chance to visit any plantations this trip but there are several only a short drive outside the city, last trip I visited Middleton Place which was absolutely beautiful. There is a ton of great shopping in Charleston, much of it right outside our door at Belmond Place. My absolute favorite store is Candlefish, a must visit in the city.
Jess Ann Kirby shares the architecture of South of Broad, Charleston South Carolina
Jess Ann Kirby visits Charleston South Carolina for a long weekend
The architecture of Charleston South Carolina's historic homes in the South of Broad neighborhood is worth a visit
Jess Ann Kirby wears a Reiss Blazer, Paige Jeans, Sam EDelman Loafers and Chloe Bag in Charleston South Carolina
The architecture of Charleston South Carolina's historic homes in the South of Broad neighborhood is worth a visit
The architecture of Charleston South Carolina's historic homes in the South of Broad neighborhood is worth a visit
The architecture of Charleston South Carolina's historic homes in the South of Broad neighborhood is worth a visit
The architecture of Charleston South Carolina's historic homes in the South of Broad neighborhood is worth a visit
Jess Ann Kirby suggests stopping at Leons Oyster Bar in Charleston South Carolina

Where to Eat

This basically deserves its own blog post. There are SO many good restaurants in Charleston it’s unreal. You could spend a week there and not even scratch the surface. From cafes, to coffee shops to bakeries and restaurants there is no shortage of amazing places to eat. We fit as many restaurants as we possibly could into our three day trip but there are so many more on our list we want to try. Here are some of my favorites:
Sugar Bake Shop is worth the visit in Charleston South Carolina


Bakeries/Coffee Shops
Sugar Bakeshop – A must visit in Charleston, and I’m not even a sweets person
Black Tap Coffee – Order the lavender latte, you won’t regret it
The Rise Coffee Bar – I tried the rosemary latte and it was so good. A cute little coffee shop in the Restoration Hotel.
Lunch & Dinner
Minero – Delicious Mexican food, order the queso!
Callie’s Hot Biscuits – We had a quick lunch here on our last day. Can’t go wrong with anything on the menu.
The Obstinate Daughter – We had to take a cab here because it’s on Sullivan’s Island but SO worth the trip. The food is SO good.
Basil Thai – We were craving Thai so walked here from our hotel. I had the red curry and Craig ordered the basil duck. It was delicious.
167 Raw – Expect a wait here, we went for lunch and there was a line out the door. But it wasn’t that long and it was WORTH IT.
Leon’s Oyster Shop – We had a great lunch here sitting outside on their patio. Craig had the frozen G&T and it was out of this world. Definitely order the fried oysters.
Jess Ann Kirby suggests eating at Obstinate Daughter in Charleston South Carolina
Jess Ann Kirby visits South of Broad in Charleston South Carolina

Where to Stay

I loved our hotel this trip, the Belmond Charleston Place, because it was SO convenient. We walked practically everywhere, and the location couldn’t be more central. Close to shopping, restaurants, the historic South of Broad neighborhood and the harbor you can really fit a lot in with such close proximity to everything. We stayed on the Club Suite level which gave us access to complimentary breakfast starting at 6:30 every morning (we are early birds so we LOVE when we can eat early). They also had water, snacks and happy hour available everyday for guests to enjoy. We also took advantage of the rooftop pool and jacuzzi during our stay. If you want convenience, I definitely recommend staying somewhere in that area.

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  1. Shloka wrote:

    I’ve never been here but it looks like a lovely place to visit!


    11.8.17 | Reply
  2. Natali wrote:

    Charleston looks and sounds so lovely and I would def. love to visit it someday. Your outfit is minimalistic and masculine perfection and I’m obsessed with blazers and bows like yours.


    11.8.17 | Reply
  3. Meghan wrote:

    Wow. Charleston looks adorable. The architecture and the colors are so cute. I am obsessed. I need to visit here. I have been seeing so many different people blogging about their travels, and it makes me so happy for people. I cannot wait to be at the point of my life where I can travel and explore the world. So exciting.
    xo, Meghan | http://tanlinesanddaisies.com/

    11.8.17 | Reply
  4. Stunning photos! I also love the bow in your hair!


    11.8.17 | Reply
  5. Kamilla wrote:

    Place looks wonderful! And the photos are so nice!

    11.8.17 | Reply
  6. Sharon wrote:

    I love Charleston! It’s so pretty and classy. Years ago my husband and I were looking into moving there. The burbs are gorgeous too. Have you been to Savannah, GA? It’s similar in a way. I love it there too.

    11.9.17 | Reply
    • Jessica wrote:

      I haven’t been to Savannah yet but it is definitely on my list, I’ve heard it’s beautiful!

      11.10.17 | Reply
  7. Vanessa wrote:

    Oh wow, that architecture looks unreal! And look at the size of those trees! Man, I’d love to visit Charleston one day and just walk through those streets for hours! Unreal.

    11.9.17 | Reply
    • Jessica wrote:

      I know aren’t the trees incredible! It really is fun to just walk around and get lost in the neighborhoods, the architecture is just so beautiful <3

      11.10.17 | Reply
  8. Erika W. wrote:

    I live in Charleston so I’m always excited to see it through other people’s eyes. You are so right about not being able to scratch the surface when it comes to restaurants. I have lived here for several years and there are still so many I haven’t had a chance to go to because I get in a routine of hitting up my favorites!

    11.9.17 | Reply
    • Jessica wrote:

      OMG you are so lucky. There are just so many amazing options I would never want to cook at home!

      11.10.17 | Reply
  9. Elizabeth wrote:

    What a fun places I would love to visit one day!

    11.9.17 | Reply