Judi Travel Caricature“What’s y’alls name?” asked our guide Cooper as we gathered near the harbor for  The Best Charleston History Tour. I had booked an AirBnb Experience in advance of Saturday morning when we would be in Charleston during my mother-daughter road trip home from Florida. My daughter A and I had enjoyed our first day exploring the downtown and were eager to learn more about Charleston’s past.

Charleston Historic District

I loved the AirBnb Experience The Best Tour of Historic Charleston

Tourists all around

Before we started our 2.5 hour walkabout, Cooper shared current stats about this charming Southern city that attracts 7.3 million tourists a year. “Charleston is a very wealthy city, with old and new money, yet 20 miles north or south is very poor,” said Cooper. He told us that Charleston and Savannah are competitors. Having visited Savannah on my road trip to Florida in 2021, it made sense since the two cities are similar in Southern-style.

George Washington's cousin's home in Charleston

George Washington modeled The White House after his cousin’s home in Charleston

So many “firsts” and “largest” in Charleston

“The first shots of the Civil War were shot over the water here,” Cooper pointed out. “We also have the largest collection of colonial buildings and were the largest richest city around the South for a long time. The very first library and horse races were started in Charleston. So was Memorial Day.”

When we passed through Pineapple Park, Cooper explained the pineapple’s relationship to Charleston: “Pineapples are a welcome symbol. In the 1700s, pineapples were very expensive. If a pineapple insignia was displayed on a person’s home it meant that they were able to afford a pineapple. The pineapple was called the king’s fruit because it has a crown on it.”

Charleston colonial seesaw

Can you see the seesaw on the porch of this colonial home?

It seems that Charleston got rich from the British merchants who sold deer skin to Europe in the early days. Slave trading was popular too. The British had Charleston, Spain had St. Augustine, Florida, and Amsterdam Dutch had New York. “Charleston to New York is still a trade route today,” remarked Cooper. “In summer 1680 Charleston was established here where it is now.”

From old to new colonial architecture

The homes near the harbor were quite large. “Charles Town was built like a castle because that’s how Europeans knew to build,” said Cooper. He pointed out the home where TV personality Steven Colbert grew up and told us that Steven now has a home on Sullivan Island, which we could see at a distance. Actor Bill Murray also lives in Charleston.

Steven Colbert's childhood home in Charleston

Steven Colbert grew up in this beautiful home on Bay Street in Charleston

Cooper was full of tidbits about colonial architecture, including the pillars and rope design on the outside that denoted wealth; the round balconies designed to accommodate women’s round skirts; and seesaws on the porch that indicated a wealthy home. He highlighted a pink house that he said was purchased 5 years ago for $7 million and then underwent $11 million in upgrades. “Contractors need to have specific skills to renovate colonial houses,” advised Cooper.

We saw George Washington’s cousin’s house which in 1701 became the house that George used as a model for the building of The White House. We passed by the famous Williams house. “The Williams house is the largest house in Charleston and was Allie’s parents’ home in the movie The Notebook. Ooh, ooh, ooh, that’s one of my favorite movies!

Williams Home in Charleston

The Williams Home in Charleston was one of the sets for the movie “The Notebook”

Symbols from the good olde days

We picked up our pace toward the end of the tour to make sure we had time to see everything. There was more history to share. “The chimney showed how many rooms have heat,” stated Cooper as he motioned upward. “A half moon on the building was the symbol for an hotel and a heart was the symbol for a brothel.”

We asked about all the gas lamps on the homes. “Hollywood puts them there,” replied Cooper. “It’s up to homeowners if they keep them. It costs about $7.00 a month to run them.

And what about those cobblestone streets? “Cobblestone is only in colonial port towns,” said Cooper. “It is cobblestone if there is no pattern. There are only 9 cobblestone streets left in Charleston.”

old hotel in Charleston

Half moons on shutters denoted an hotel in colonial times

Fun things to see and do and great places to eat in Charleston

Before he said his goodbyes, Cooper offered up his favorites when it comes to fun things to see and do and places to eat in Charleston. Here’s the local scoop:

For great hamburgers stop by Big Gun.
For Bill Murray’s place, head to Harold’s Cabin farm to table restaurant.
For home cooking, go to Page’s Okra Grill.
For best breakfasts, try Millers All Day Bistro & Bakery.
For a nice to see sunset and shrimp coming in, visit Shem Creek.
For a beautiful sunset cruise book Palmetto Breeze.
For classic cocktails sip at The Belmont.
For delicious desserts, stop by Carmella’s Cafe and Dessert Bar. Cooper says the espresso martini will wake up your ancestors.”
For the best ice cream in town, enjoy Jeni’s.

Jeni's King Street

Ice cream from Jeni’s King Street

Except for Jeni’s, A and I didn’t have time to visit any of these establishments or do more touring since we were leaving the next morning. So you know what that means? I guess I’m going to have to visit Charleston again for another vacay and I highly recommend y’all plan a vacay in the future there too. To get you thinking here’s the link to the #ExploreCharleston website.

Meantime, in the words of Beverly Hillbillies Granny Moses: “Set a spell, take yer shoes off, y’all come back now, hear.”