Explore Charleston: Weekend Hit List

Defined by its cobblestone textures, cotton candy painted houses and rich history, Charleston is the true gem of Lowcountry.  Upon seeing Charleston referenced in multiple travel articles I had my heart set on visiting and this past October the perfect opportunity came up.  Fortuitously, I was heading to the Sanctuary, Kiawah Island to host a golf trip early Fall which I coincidentally read was the perfect time to visit the Holy City.  I invited a girlfriend to explore Charleston with me and we flew in for one weekend before I was scheduled to drive down to Kiawah Island for ‘work.’  (Tough job I know)

Generally, when I travel to a new city, I make a short list of ‘must-see’ restaurants, photo spots, experiences, bars, and adventures to ensure I maximize limited time in a new destination.  Upon doing some simple online research it became clear quickly that Charleston was going to be an adventure centered around…EATING.  From renowned oysters to fried green tomatoes, Charleston boasts flavors of the south that literally had us eating five meals a day.  Both my girlfriend and I are super active by nature so in order to counter-balance the number of consumed calories we decided we would bike the entire city to each destination, near and far.  This turned out to be the perfect plan for sightseeing and waist watching. 

Charleston is best explored by bicycle as you could spend a day getting lost in the culture-rich neighborhoods full of gas lanterns, pretty painted houses and cobblestone streets all radiating with southern charm.  After spending one weekend of urban discovery in the Holy City, my greatest hit notes to add to your ‘must-see’ list are recommended below. 


Broad Street; art galleries

Chalmers Street; some of the oldest cobblestone

Church Street: Where you will find…churches, duh

East Bay Street; an instagrammers playground of photo opportunities

King Street; nightlife and shopping

Queen Street; some of the city’s most prestigious and delicious restaurants

Legare Street; walls and courtyards dressed with gardens and ivy


Poogan’s Porch; dinner, fried green tomatoes, southern cuisine, she crab soup

explore charleston

Callie’s Hot Little Biscuit; breakfast or lunch, southern biscuits, multiple locations

explore charleston

5Church: dinner, ambiance, set in an old church, the entire book of “The Art of War” is hand-written on the walls

explore charleston

Butcher and Bee; brunch, seasonal menu of local rotating ingredients, shakshuka, specialty cocktails

Sugar Bakeshop; scratch baking, local ingredients, cupcakes

Peace Pie; ice cream sandwiches with a layer of pie filling

Goat. Sheep. Cow; gourmet specialty cheese shop, grab supplies for a picnic and head to the park

explore charleston

167 Raw; dinner, tacos and crudos, raw bar, intimate setting, lobster rolls, po’ boys

explore charleston


27 State Street Bed and Breakfast; perfect location in the French Quarter, two courtyards, huge room, reasonable prices, outstanding hospitality and cleanliness, incredibly preserved 1814 residence


The Grand Bohemian Hotel; art gallery, live music, open-air, champagne specials

explore charleston

The Commodore; locals bar, less college kids, incredible live music, cool vibe, southern charm, cheap drinks

explore charleston


Holy Spokes; Official bike share of Charleston, South Carolina, download the app, reserve and go

explore charleston

Brewildered Tips

Curls: If you have curly hair, you can leave your hair products behind, the humidity in Charleston created the best hair days EVERY day.  We never touched our curling irons and indulged in the glorious natural textures from the moisture in the air.

She crab soup:  This was a very common item on the southern cuisine menus and the ingredients include; Atlantic blue crab and crab roe bisque mixed with sherry.

This is a handsome life.



  1. Bre,

    Thank you so much for featuring Holy Spokes Bike Share in your blog.
    We are thrilled to know you enjoyed the city in the best way to experience it. We would love to share your visit on our social media with your permission.



    • 100percentday
      January 15, 2019 / 5:45 pm

      Hi Ian,

      Thank you so much for reading. We absolutely loved the bikes. Yes, please feel free to share.


  2. Kathleen Riehl
    January 15, 2019 / 5:49 pm

    It looks so beautiful there! The food looks amazing, I’m hungry now! ; )

    • 100percentday
      January 15, 2019 / 5:57 pm

      The food was amazing and biking really helped keep off the extra pounds. I am ready to go back!

  3. Tammi
    January 15, 2019 / 6:19 pm

    Can’t wait to head back south—maybe a girls trip?! Biking the city sounds genius!! Looking forward to some great meals on 2019!

    • 100percentday
      January 15, 2019 / 6:47 pm

      Girls trip eating our hearts out in any city sounds amazing! I am in!

  4. Sue Terry
    January 15, 2019 / 7:39 pm

    Omg, this looks amazing, adding Charleston to my bucket list, thanks for all the info!

    • 100percentday
      January 15, 2019 / 7:55 pm

      Thanks for reading!

  5. January 15, 2019 / 9:38 pm

    Gorgeous photos! Makes me want to hop on a plane to Charleston right now! I’ve never heard of She Crab Soup before but it sounds sooo good.

    • 100percentday
      January 15, 2019 / 9:43 pm

      Its all so delicious you really cannot go wrong!

  6. January 15, 2019 / 10:48 pm

    How adorable. I may need to reroute my next girls trip to Charleston!!! That sweet shop and the ice cream sandwiches look devine! Thanks for sharing!

    • 100percentday
      January 15, 2019 / 10:49 pm

      The sugar bakeshop was actually voted number one by Martha Stewart! LOL…it definitely has my vote too!

  7. Cam Azari
    January 15, 2019 / 11:53 pm

    Great post Bre. I’ve been to Charleston twice and loved it, but you found so much more to do there than I realized. The 1814 BnB looks so cool.

    • 100percentday
      January 16, 2019 / 1:30 am

      Thanks for reading. Guess you will have to make a third trip to try some of my suggestions!

  8. Jessica Lockley
    January 16, 2019 / 1:56 am

    I have always wanted to go here and now I reaallllllly want to. Looks divine. Go again with me some day please! Xoxo

    • 100percentday
      January 16, 2019 / 3:15 am

      I would love to go with you anywhere!! xoxo

  9. January 16, 2019 / 3:36 am

    What a great idea to use bike so you can see more of the city while also burning the calories!

  10. January 16, 2019 / 4:10 pm

    Your trip look amazing!!! Charleston is definitely on the list of places I want to visit! Now I know exactly what I’m eating when I’m there!

    • 100percentday
      January 16, 2019 / 5:01 pm

      You would absolutely love it there Erin!

  11. January 16, 2019 / 8:48 pm

    Well looks like I need to visit Charleston! I love that pink building with the ivy, so pretty.

  12. Rachel Farrell
    January 18, 2019 / 11:24 pm

    Uh, those biscuits….mmmmmm.

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