My memory of Charleston was walking on a cobblestone street, thinking to myself what a quaint little city Charleston was. I was there for work, on an overnight layover. Because there wasn’t enough time to fully explore the city, I pledged I would come back on my own. I was mesmerized by the colorful buildings (locals say the cityscape looks like it has been painted in watercolor), the abundance of trees, beautiful colonial homes, and historic churches— truly a southern city with old world charm.

Since then, I got busy. I got married, moved across the ocean to live in another country, became a mom, moved back to the United States, started a new career, became a mom again to a second boy, and let’s just say, it only took twenty years before I could go back again! If not for my cousin’s wedding in Asheville (North Carolina), Charleston would’ve remained a distant memory, waiting to be revisited.

A lot of things can happen in twenty years.  Charleston is now known as one of the most spectacular cities and hottest destinations in the United States. In fact, it was named by Travel and Leisure as the #1 city in North America. When my cousin invited us to her wedding down south, I thought, why not detour to Charleston? My mom is here in the US and my older son isn’t going back to college until late September. But plans have changed and my son’s schedule became a bit complicated. So I was now going with my mom, my two aunts, and my cousin. Traveling with a big group, as expected, complicates the itinerary. Everyone had different ideas of where to eat, where to go, what to do…and this was the trip that helped solidify my desire for solo travels in the future.

Things To Do:

King Street in downtown is the ultimate shopping experience. The three-mile shopping promenade is lined with stores (mostly boutiques) and restaurants. It’s probably a good idea to book your hotel on this street or nearby. It’s fun to stroll on King Street for shopping, finding a place to eat, or just people watching.

King Street

The Rainbow Row is an iconic street near the historic waterfront (Charleston Harbor) best known for the 14 houses that are painted in the colors of the rainbow.

Rainbow Row

There are several speculations why the houses were painted in such a way. According to some tales, the houses were painted in the various colors to help intoxicated sailors to remember which houses they were staying in. Another version was that the colors were used as markers (to make it easier for slaveowners to tell their illiterate slaves which building to go to for shopping).

Along the Charleston harbor, you will find the Pineapple Fountain, a focal point of the Waterfront Park. As the name implies, the fountain is shaped like a pineapple, a symbol of southern hospitality.

One of the absolute must-see places while visiting Charleston is the Angel Oak Tree located on John’s Island. This live oak tree is believed to be about 400 to 1400 years old (no one can pinpoint the exact age) and astounds visitors by its canopy extending to 2,000 square yards. Before her death, a  local civil rights activist by the name of Septima Clark told stories of her relationship with the oak tree. During the segregation, black families would picnic by the tree’s enormous branches, but stopped when the tree became sacred, respecting its surrounding grounds.

It’s also significant to know the history of the tree before snapping your photo to post on Facebook or Instagram: there was a time that the tree was used for lynching, a painful reminder of our country’s history of violence and prejudice. I’ve seen photos of smiling faces (I wish I had not posed in such a way, a mistake I’d like to point out), or even a marriage proposal that took place there. I’m usually a researcher at heart and why I missed this important piece of history, I have no idea. But I found out a little too late. I blame it on the company. 😆 Surely traveling with too many people can get distracting.

Avenue of the Oak
The summer home in the movie, The Notebook

If you’re a historian or a sucker for romantic movies, Boone Hall Plantation is the perfect place for you. It is one of America’s oldest plantation that begins with the breathtaking entrance driveway, the Avenue of Oaks, lined with giant live oaks. And bordering these giant oaks houses eight original slave cabins, the only brick slave street in the U.S.

Not too far from the plantation is the Deep Water Vineyards/ Firefly Distillery.

South Carolina is a state with an appetite for alcohol, and if you’re looking for a drink that has any historical meaning, look to rum. Back in the 18th century, it was the main swill of South Carolina drinkers. Firefly Distillery is dedicated to crafting high quality rum although they were made famous by their tea vodka. My aunt had vodka tasting of the different and interesting flavors they came with.

Lemonade, strawberry, sweet tea, and peach were among the flavors.

We all had wine tasting and were given seven to choose from. My aunts are from California and proclaim themselves as wine connoisseurs. None of us liked the wine, thinking South Carolina’s grapes were young and the weather was not suitable for vineyards. I’m no expert but the wines, in my opinion, were quite bad.

My mom, cousin, and aunts during wine tasting

I was also disappointed with the foods I ate in Charleston. Granted, I wasn’t able to go to some of the acclaimed restaurants (again, blaming it on the company lol), but I doubt if it was just bad luck that each restaurant we patronized ranged from mediocre to bad. You would at least expect one of the six or seven to be okay. But nope, not even one satisfied my palate. Food is important to me when I’m traveling (especially I’m a self proclaimed foodie 😊). I expected a lot from Charleston, especially after being voted as the #1 city in North America. But just like any other city that experiences a tourism boom, change is expected. It may no longer have that old world feel but the city’s charm and beauty remains.