Chicora Walk: An American History Tour

Chicora Walk: A Historical Tour of Charleston

The Chicora Walk has been selected by TripAdviser users for a 2021 Traveler's Choice award - Best of the Best. Almost every guest has told us that we have created the best walking history tour in Charleston. On our walk through one of the oldest cities in America, we will explore the tapestry of American history. Established in 1670, Charleston grew to become one of the nation’s leading ports and was an especially important for trade and military defense in the South. In fact, by 1750 Charleston was the largest and wealthiest city south of Philadelphia.

Our guides love to pull you into the narrative of Charleston's rich and fascinating history. From its wealth and opulence to the many disasters that fell upon this great city. We also explore its place in the darkest parts of American history and humanity. As a city abound with generations of opportunity, people of great diversity came from near and far to participate in the building of one of the early melting pots in America. Charlestonians built enduring structures; houses, churches, businesses and forts all with their own stories to tell. These streets and structures have been walked by presidents and foreign dignitaries, generals and soldiers, slaves and slave traders, and pirates and merchants. You will feel a part of the celebrations held for visiting presidents to the devastating fires, earthquake, hurricanes along with attacks by foreign invaders, pirates and eventually Union armies that were defended against.

Let's Take a Walk

"History is a mighty drama, enacted upon the theatre of times, with suns for lamps and eternity for a background.”
Thomas Carlyle

Trip Advisor Traveler's Choice 2021 Best of the Best

Plan Your Tour


$25 per ticket


Starts 10AM Daily,
Duration 2 Hours

Starting Point

Bitty & Beau's
159 Church St.
Charleston, SC

We had an amazing time! Have not stopped talking about it and all of the stories we learned. You have such a gift of story telling and your passion and knowledge of the city make your tours amazing!! - Jennifer P. (Florida)

The Badass Broads tour is truly badass. Jonathan' knowledge and passion for Charleston's history is simply amazing. We laughed, we cried and enjoyed every minute of it. - Warren G. (Texas)

“Chicora” are the fresh coastal breezes that add to Charleston’s charm and natural beauty. Legend has it that during a particularly deadly outbreak of disease the natives suggested that their foreign neighbors move down to the peninsula where the healing, “chicora” breezes would restore their health. It may be that these breezes also limited the population of mosquitos that were vectoring their ailments and so the settlers indeed found improved health. They probably found other things such as fertile soil and other resources that made it an ideal place to build give rise to Charleston, South Carolina. 

Tour of the Tour

St. Philip’s Episcopal Church

  • Oldest congregation in Charleston
  • John C. Calhoun, 2 time VP buried here
  • Christopher Gadsen, William Rhett, Charles Pinckney and Edward Rutledge buried here
  • Four degree tilt due to earthquake of 1886
Oldest congregation in Charleston, John C. Calhoun, 2 time VP buried here, Christopher Gadsen, William Rhett, Charles Pinckney and Edward Rutledge buried here, Four-degree tilt due to earthquake of 1886

Dock Street Theater

  • First building in America to be used for theatrical performances
  • Destroyed in Great Fire of 1740
  • Reopened as Planter’s Hotel in 1809
  • Planter’s punch invented here
  • Reopened in 1937 as a theater
  • Reopened in 2010 as a theater
Dock Street Theater

French Huguenot Church

  • Also known as the Church of the Tides

Chalmers Street

  • One of 8 remaining cobblestone streets in Charleston

The Pink House

  • 2nd oldest house in Charleston

Ryan’s Mart

  • 40 to 50 slave markets
  • This is the only one that is still standing
  • Currently a museum
  • 40% of all slaves brought to this country came in through the port of Charleston
  • Here we discuss this part of our city’s history
Ryan's Mart

8 ½ State Street

  • Discuss different architectural features and why Charleston is one of the most well-preserved cities in America

Old Exchange

  • Built in 1771
  • It is the last building built with British money
  • This was a gift from the British
  • August 1776, the Declaration of Independence was read to the citizens of Charleston from these steps
  • In 1788, the Constitution was ratified by South Carolina in this building
  • In 1791, President Washington visited and a three-day ball was held for him where he danced with over 250 women
Old Exchange

Rainbow Row

  • Originally merchants’ homes
  • Shops were on the first floor and the merchant’s families lived on the second and third floors
  • Was rehabbed in the 1930’s
  • Painted these colors to celebrate our connection with Barbados
Rainbow Row

Robert Smalls

  • Born into slavery
  • Was sent to Charleston and became a wheelman in the harbor
  • Assigned to the CSS Planter
  • Stole the ship and turned it over to the Union
  • He became a Captain in the Union Army
  • Returned to Beaufort after the War and bought the plantation that he was born on
  • Served one term in the South Carolina General Assembly and five terms in the US House of Representatives
Robert Smalls

Stoll’s Alley

  • We will see several great examples of ironwork made by Philip Simmons
  • Philip Simmons was one of the most well-known blacksmiths in America

Let's Take a Walk

  • star rating  What a great experience! Jonathan is extremely well versed in the History and Culture of Charleston. The walk was very manageable with many stops along the way at... read more

    Mark W
    November 1, 2021

    star rating  Johnathan was so knowledgeable and passionate about what he was teaching us. I have been on a few tours of the city and no one does it like him. Also... read more

    Alysia Taylor
    November 1, 2021

    star rating  My girlfriend and I took this tour last week. Where to begin? I'll start by saying that this may have been the best walking tour that I've ever experienced, and... read more

    Jovy Berrios
    November 1, 2021

    star rating  This tour was worth every penny and then some! Do you feel like hearing stories that are funny, powerful and inspiring? Then this is the tour for you. Jon was... read more

    tara s
    November 1, 2021
  • star rating  Walking tours don’t get better than this! Jonathan is very passionate about the history of Charleston and it really shows in his tour. I’ve learned a lot about the city... read more

    Devon L
    November 1, 2021

    star rating  Jonathan made this tour of the Badass Women of Charleston the best walking tour we’ve ever taken! He is so knowledgeable, passionate and sensitive about the history of Charleston.... read more

    Valerie S
    November 1, 2021

    star rating  This was a kicka** tour! Jonathan was super knowledgeable and a fantastic speaker. As a local, I know a good bit of Charleston history to this tour added so much... read more

    October 1, 2021

    star rating  Jonathan was terrific. He's a recent "transplant" to Charleston, but his love for the city was apparent throughout the entire time we spent with him. We've been on walking... read more

    Gene S
    October 1, 2021
  • star rating  Jonathan was an excellent tour guide and it was so much fun (even as a local) to learn about a different side of the holy city. Would definitely book another... read more

    Laurel W
    October 1, 2021

    star rating  This was a delightful, informative, engaging & interesting tour. Jonathan is an excellent tour guide. He obviously knows his stuff, is enthused about the subject & loves the city.... read more

    Rhonda S
    October 1, 2021

    star rating  Jonathan is an amazing tour guide. He brought Charleston's historic district to life with his engaging stories. He was enthusiastic and dynamic, offering detailed answers to our questions. It... read more

    Karel H
    October 1, 2021

    star rating  Jonathan’s knowledge and passion for this beautiful city is extraordinary. I’ve lived here for 15+ years and learned so many cool things about history and some of the women who... read more

    October 1, 2021
  • star rating  Jonathon was fabulous! Far more than just a history of bad*** women, he covered architecture and other history as well. This was by far the best tour I took in... read more

    October 1, 2021

    star rating  This was my second time in 6 months doing the tour....THAT good! We are a small group of life friends gathering in my newly adopted home town odf Charleston.... read more

    October 1, 2021

    star rating  Jonathan was one of the most passionate and informative guides I've every experienced. The Badass Women of Charleston tour was entertaining, enlightening and educational. So much of history... read more

    nancee m
    October 1, 2021

    star rating  The tour was a taste of culture ,history, architecture, and humor. Jonathan does a brilliant job of bringing all of these things together in such a magnificent manner.The two hours... read more

    September 1, 2021
  • star rating  I booked the tour for myself and a friend visiting from NJ. I had taken two previous tours with other companies in the past six years I have lived in... read more

    Kim K
    September 1, 2021

    star rating  Amazing tour and tour guide! Super knowledgeable, fun and informative. You could tell he loved and knew the city, and treated some of the darker parts of Charleston’s history with... read more

    Amanda D
    September 1, 2021

    star rating  Jonathan is super knowledgeable and a great story teller - we learnt a ton on the history of Charleston and it felt very personalized - a great way to get... read more

    September 1, 2021

    star rating  We had such a good time! Jonathan kept us laughing and attentive. We learned so much wish we could have recorded it. Questions a long the way... read more

    Pat S
    September 1, 2021
  • star rating  So many choices for which Charleston walking tour to take, but I finally chose this one online and hoped for the best. Boy was it the best! Way... read more

    Glenn K
    September 1, 2021

    star rating  Excellent tour! Highly recommend. Incredibly knowledgeable and personable. Well worth your time and money.

    Chris B
    August 14, 2021

    star rating  There's so much to do in Charleston and often with little time - this was time and money very well spent. This tour is a must do for your trip... read more

    Benzi J
    August 9, 2021

    star rating  PLEASE DON’T MISS THE J TOUR “BAD ASS BROADS TOUR” while you are in Charleston. It is AMAZING!!! Jonathan brings an unparalleled passion, incredible historical knowledge, extraordinary... read more

    Susan R
    August 7, 2021
  • star rating  We've done several other walking tours of Charleston over the years. Jonathan's tour was refreshingly different. If you are looking for a detailed recounting of Charleston's history, read a book... read more

    August 1, 2021

    star rating  Absolutely amazing walking tour. Jonathan is vibrant, outgoing, down to earth and a great storyteller. He made the city and it’s history come alive. You will not be disappointed!!!

    Jeffrey J
    July 26, 2021

    star rating  My family and I had such a great day exploring Charleston with our tour guide, John! He was so knowledgeable, friendly and full of energy! We did not want our... read more

    Christina S
    July 25, 2021

    star rating  My husband & I loved this tour & had a great time. Jonathan really researched the badass broads featured on the tour & is clearly passionate about his career. ... read more

    Molly L
    July 15, 2021
  • star rating  Going in to this tour I didn't really know what to expect. To say it was amazing is such an understatement. Jonathan was an absolutely outstanding tour guide. His stories... read more

    July 14, 2021

    star rating  I recently joined Jonathan on his Badass Broads tour. The experience was incredible. Jonathan’s wealth of knowledge about the city and its history paired with his innate story-telling abilities brought... read more

    Mallie S
    July 14, 2021

    star rating  Man, I'm so glad we chose JWalk tours. Jonathan is the owner and you can tell that teaching, learning and unearthing the past is his passion. I've lived... read more

    Zoe S
    July 13, 2021

    star rating  Where to begin?! Jonathan is an unbelievable sponge of history knowledge! The level of passion and history knowledge are unmatched. I thoroughly enjoyed this tour and learned so much about... read more

    July 12, 2021
  • star rating  Well planned and fun! This is a great ‘off the beaten path’ of Charleston history- highly recommend this tour. Jonathan was great- thank you!

    Jen M
    July 12, 2021

    star rating  This is a must-book option in Charleston. Locals and tourists alike will enjoy this amazing tour. The tour guide is incredibly knowledgeable and a wonderful story teller that will keep... read more

    July 12, 2021

    star rating  Highly recommend JWalk Tours. Great guide with a passion for all things Charleston. Look forward to returning for his future tours.

    Susie B
    July 7, 2021

    star rating  Great tour. Lots of cool history and fun guide! Very professional and well researched tour showed us all the highlights! Way better than our carriage ride.

    Yasmin O
    June 22, 2021
  • star rating  An excellent tour!

    Provides a different take on some history of Charleston. Jon is a fantastic guide. Intelligent, sensitive and incredibly knowledgeable. I would hire him again for any... read more

    June 20, 2021

    star rating  An excellent tour! Provides a different take on some history of Charleston. Jon is a fantastic guide. Intelligent, sensitive and incredibly knowledgeable. I would hire him again for any... read more

    Dan L
    June 20, 2021

    star rating  John was an incredibly knowledgeable and charming host. His approach to the history of the city was mostly focused on key stories/figures, which was very engaging. Also, as... read more

    June 18, 2021

    star rating  Jonathan was extremely professional, informative, fun, and a wonderful guide. We learned more about Charleston in the perfect amount of time than we would have imagined. Highly recommended!

    June 14, 2021

JWalk Tours

Let's Take a Walk

Visit Charleston, SC and take a walk with us! " Walking the streets of Charleston, one of the oldest cities in America, is walking through an important part of the tapestry of American history.

Contact Info
Questions + Booking Group and Private Tours

+1 843-608-1911


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