By Jax Stys · Last updated: October 2026
Quick answer: I just wrapped up a 9-day trip from Cleveland, Ohio to Folly Beach and Charleston, South Carolina, with my 27-year-old son Jake, from August 21 to August 28. We split our stay between a beach condo on Folly Beach and a hotel in downtown Charleston, mixing sunrise beach walks with history-packed stops like Magnolia Plantation, the Angel Oak Tree, and the Powder Magazine. It was my first real trip of this new travel chapter, and it turned into one of my favorite experiences with my son.
The first night, we ate pizza out of the box and walked the beach with flashlights.
We’d left Cleveland at 5:30 that morning. By the time we pulled into Folly Beach around 7 p.m., neither of us wanted to go anywhere. So we ordered from Piasano’s Pizza Grille on James Island and walked down to the water in the dark. No crowds. Just waves. That walk set the tone for the whole trip.
This was 9 days with my son Jake, from August 21 to 28, split between a beach condo and a downtown hotel. It was my first big trip of what I’ve been calling my travel era. Here’s what we did, and some of the history we picked up along the way. If you want the practical side, like packing and long-drive tips, I put those in my road trip travel tips.
Folly Beach and downtown Charleston are two completely different experiences. Folly Beach gave us slow mornings, sunrise walks, and beach afternoons. Downtown Charleston gave us cobblestone streets, walking tours, and centuries of history around every corner. Staying in a condo for the beach portion also meant we had a kitchen to cook some meals in, which saved money, and more space to spread out for several days at a time.
I’d do it this way again. Would you pick the beach or the city if you could only have one?
For us, about 13 and a half hours, door to door, with stops. We left at 5:30 a.m. and got in around 7 p.m. Long, but it meant we still had an evening once we arrived.
Nearly every morning of the trip started the same way: up early for a sunrise beach walk, followed by coffee. It became my favorite part of the trip, and the easiest habit to bring to any beach vacation.
One of the highlights of our time on Folly Beach was the Morris Island Lighthouse Trail. The story behind that lighthouse is one of the more interesting pieces of history we came across all week. The very first lighthouse near that spot dates back to 1767, before the United States was even its own country. The lighthouse standing there today was finished in 1876 and stands about 161 feet tall. Here’s the part that got me: it was originally built on solid ground, but over the last century and a half, so much of the surrounding coastline has eroded away that the lighthouse now sits offshore, a few hundred feet out in the water. The land disappeared around it, not the other way around. It even leans slightly, which many believe happened because of an earthquake back in 1886.
We also rented a golf cart to get around the island, which turned out to be one of the easiest and most fun ways to explore Folly Beach without dealing with parking every time we wanted to go somewhere.
One of the mornings, we toured Magnolia Plantation, and this was a stop I’d been looking forward to for a while. Magnolia dates back to 1676 and has been owned by the same family, the Draytons, for over three centuries. It’s considered the oldest public garden in the entire United States, having opened its doors to visitors back in 1870, which means people have been walking these same garden paths for more than 150 years.
Magnolia was originally a working rice plantation, and the tour didn’t shy away from that history. The labor and lives of enslaved people are a real and heavy part of this land’s story, and Magnolia now offers a tour specifically focused on that piece of its history as well. The gardens are beautiful. The history is heavy. I didn’t want to skip past one to get to the other.
When we made the switch to downtown Charleston for the second half of our trip, the pace and the scenery changed completely. We did a self-guided walking audio tour through downtown, which is one of my favorite ways to explore a new city. You get real stories and details you’d completely miss just wandering around on your own, and Charleston has centuries of colonial-era buildings still standing, so there was a lot of ground to cover.
One of my favorite stops downtown was the Powder Magazine. Built in 1713, it’s the oldest public building still standing in the entire state of South Carolina. Back then, Charleston was one of only a few walled cities in early America, and this building was used to safely store the city’s gunpowder supply. The walls are more than two feet thick, and the whole structure was designed so that if an explosion ever happened inside, the force would blow up through the roof instead of out through the walls, protecting the rest of the city around it. It’s also considered one of the more haunted spots in Charleston, which came full circle for us that same evening on a Ghost and Graveyard walking tour that wound right back past some of the same historic buildings.
Another highlight was our visit to the Angel Oak Tree on Johns Island. Depending on which historian you ask, this tree is somewhere between three hundred and five hundred years old, and some believe it could be even older, possibly over a thousand years. Either way, this tree was already standing long before Charleston existed as a city.
The tree stands about 65 feet tall, but its canopy stretches across roughly 17,000 square feet, and its longest branch reaches more than 180 feet out from the trunk. It’s not named after angels from heaven, either, which is what most people assume. It’s actually named after the family who once owned the land, the Angels. Standing under something that old puts a lot of things in perspective.
We also spent a day at Sullivan’s Island for a change of scenery from Folly Beach, and this stop came with its own important history. Sullivan’s Island was used as a quarantine station in the 1700s and 1800s for enslaved people being brought into Charleston Harbor before they were sold, a piece of history that deserves to be remembered alongside the beach itself. The island is also home to Fort Moultrie, which played a role in the Revolutionary War, so even a relaxed beach day there came with real historical weight attached to it.
Traveling with a 27-year-old is such a different experience than traveling with a young child. There was no stroller, no nap schedule, no meltdowns to plan around. Instead, it felt like traveling with a good friend who happens to share your DNA and thirty years of inside jokes.
We split up the planning between us, compromised on what we each wanted to do, and had some of our best conversations of the entire year during the long drive down and back. I raised him by myself, and for years every trip was me planning everything and him along for the ride. This time we were two adults figuring it out together.
This trip was my first big step into a new chapter of travel, and it will not be the last. My list is already growing, Boston, Philadelphia, St. Augustine, Chicago, New York, New Orleans, Savannah, Pittsburgh, Quebec City, Montreal, Toronto, Niagara Falls, and Ellicottville are all on my radar for the next few years. My goal is four to six trips a year, mostly short getaways here in the U.S. to start, built around history, walking, and good stories.
I’m going back to Charleston in February 2027, solo this time. That will be a different kind of trip without Jake, and I’ll tell you how it goes.
Where’s the first trip on your list? I’d love to know.
Both offer very different experiences, and splitting a stay between the two allows visitors to enjoy a relaxed beach atmosphere at Folly Beach alongside the walkable, history-rich streets of downtown Charleston, rather than choosing just one.
Notable historic sites in the Charleston area include Magnolia Plantation and Gardens, the Angel Oak Tree on Johns Island, the Powder Magazine in downtown Charleston, and Fort Moultrie on Sullivan’s Island, each offering a different window into the region’s colonial, natural, and cultural history.
It took us about 13 and a half hours with stops. Leaving early, around 5:30 a.m., made it doable in one long day.
Yes. Charleston’s mix of beach relaxation, walkable history, and varied activities makes it well-suited for multigenerational or parent-adult child trips, offering enough flexibility for both structured sightseeing and unstructured downtime.
