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Beautiful Surprises and Silliness on Our Visit to Charleston, SC

Our annual girls weekend trip to Charleston, SC, was marked by detours that made it all the more fun for our intrepid travelers.

“Hang on, everybody!” someone shouted from the rear-facing seat of the golf cart.

“All hands and feet in the vehicle!” hollered another NextTriber from the front.

NextTribe is offering our annual spring trip to Charleston again in March 2024. Find out more about this and other curated travel here.

Then, with the sound of the wheels spinning across gravel and laughter from eight women squeezed in the three seats, we were off for a wind-in-your-hair tour of Sullivan’s Island, one of the gorgeous barrier islands across the harbor from Charleston, SC. This is the way locals get around on the small island, which is known for its role in two US wars and for the spectacular low-slung beach cottages with porches galore and plenty of history.

And this was an entirely unplanned part of the NextTribe tour.

Surprises are often a part of any travel plans, but on this NextTribe trip to Charleston, SC, we had many—many surprises that brought us closer together, closer to the culture, and closer to new, long-lasting friendships.

Read More: Can 11 Women Become Best Friends in One Weekend?

Surprise Detours 

Cavorting on the uninhabited barrier island before our beach cookout

We added the golf-cart ride at the last minute, after rain delayed our departure on a boat trip to Caper’s Island, an uninhabited and much tinier barrier island. We made our way through the palmetto-tree-lined streets like a band of bachelorettes. We hooted as we passed along the short row of shops on the no-stoplight island, and we hollered as we cruised under the ancient oak trees dripping in Spanish moss. We waved at other passing golf carts and got caught in traffic as a police car clogged an intersection.

“I hope this is legal—eight women in a six-person cart,” I shouted. Fortunately, the police had something more important to tend to.

We hooted and hollered and waved at other passing golf carts.

Then, as the weather cleared and our battery charge lowered, we returned to our starting point, the home of NextTriber, B. McKie. This is where earlier in the day we had enjoyed an eye-popping and belly-filling lunch of handmade biscuits, fruit, and cookies by entrepreneur and author of Callie’s Hot Little Biscuits, Carey Morey. She shared with us not only her cookbook but also how she parlayed a love of baking biscuits into a thriving online, local eatery and food truck business.

Then we were off on a boat ride and a beach picnic that was made even more beautiful than expected after the rain had cleansed the air and the clear skies gave way to a deep russet sunset.

Unexpected Hospitality

Charleston for women over 50

At Circa 1886 at the Wentworth Mansion for dinner with the owner Linn Lesesne, center.

Another pleasant surprise earlier in the trip was having, Linn Lesesne, a NextTribe member and vice president of Charming Inns, join us for dinner. Linn and her husband are the proprietors of Kings Courtyard Inn, where we stay during our time in Charleston, and the gloriously renovated Wentworth Mansion, one of the city’s best hotels. Every year on our Charleston trip, Linn meets us at the mansion’s door with champagne and leads us on a tour up to the rooftop, where we get a sweet view of the harbor and the bridges connecting this historic downtown peninsula to the rest of the city.

The attention was appreciated. But not as much as his next gesture.

We then normally head to the hotel’s renowned restaurant Circa 1886 for a welcome dinner. This year, Linn sat down with us for dinner, which was an extra treat, because she is a born-and-bred Charlestonian and prominent in the city’s culture today. Between amazing courses (garlic striped bass, truffle risotto) and wine, Linn graciously shared stories of growing up in Charleston, meeting her husband, raising her children, and running a business combining the preservation of historic buildings with Southern hospitality.

Another pleasant surprise came during the famous Gospel Brunch at Hall’s Chophouse, another top Charleston restaurant. The owner Billy Hall stopped by our table twice to greet us and thank us for coming to his restaurant. The attention was appreciated. But not as much as his next gesture. He sent three decadent desserts to our table—ginger crème brûlée, Southern caramel cake, and whiskey bread pudding. We felt special and seen—in a way that women of our age normally don’t feel—and afterward we felt over-the-top full and happy.

Who Put That There?

Charleston for women over 50

At Hall’s Chophouse for brunch

The last evening together, we had one more surprise, which offered a memorable and funny (at my expense) way to end our wonderful tour. After an immersive experience learning all about Gullah cooking with Charlotte Jenkins in her family home, we returned to downtown Charleston. The night was young, so we decided to have a drink atop the roof of the Market Pavilion.

I let everyone out of the van so they could go on up. Then I handed off the keys to the valet and took the elevator to meet them. As I exited, I saw my lovely new friends sitting together and walked straight toward them. I had no idea that there was a clear partition enclosing their space, and I walked right into it . . . bang!  A roar of laughter went up. What a surprise!

I sat down and raised a glass with the group. My ego was a little bruised. But my heart soared.

The extra-beautiful sunset, as seen from our boat on the Intracoastal Waterway

Read More: How Strangers Became Friends on Our Charleston Getaway

By Ellesor Holder

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