Every year, Thrifty Traveler picks a city and meets up for our annual team retreat. This year’s destination: the vibrant, coastal city of Charleston, South Carolina.
The lovely southern city hosted our group fir three short, packed days under the South Carolina sun. Organized by the Thrifty Traveler co-founders, we all look forward to our annual team retreat that brings together a team that lives across five U.S. states on both coasts and in the Upper Midwest. We all relish getting together to eat, drink, and sight-see through a different city every year.
In previous years we’ve visited Oaxaca and Isla Mujeres in Mexico and Asheville, North Carolina. But some pristine South Carolina weather and a city chock full of good eats and sights made Charleston a perfect October retreat this year.
We highly recommend you visit Charleston. Here’s what you should consider doing if you book a trip for yourself.
Why Charleston? We Followed the Flight Deal
This year, Charleston became a top candidate because, as we always preach to our readers and subscribers, we followed the flight deal. Flights are often the costliest part of any trip, which is we always encourage travelers to book their flights first, then figure out the rest. That’s exactly what we did when flight prices to Charleston from dozens of cities dropped earlier this year.
Here’s an example of our latest Thrifty Traveler Premium flight deal to Charleston, showing just how cheap it can be to fly there from these cities.
Charleston (CHS) routinely pops up as an airport that is cheap for Americans to fly to because of robust service from cities all over the country. Only our Senior Award Deal Analyst Peter, who lives in San Diego (SAN), couldn’t wrangle a nonstop flight to CHS. Even our Hotel Deal Analyst & Award Travel Reporter Long, who resides in Seattle (SEA), was able to hop a nonstop Alaska Airlines flight to Charleston.
We followed the deal to South Carolina, and planned our retreat around the cheapest dates to fly. And we didn’t regret it.
The Best Things We Saw
There’s no shortage of things to do in Charleston, but it’s perhaps most perfect for a long weekend trip. Besides the incredible food and drink we enjoyed in the South Carolina sun, there are a few can’t-miss activities that made our trip extra special.
One note before we dig into the tours themselves: Uber is widely available in Charleston and easy-to-use. To get our team from A to B, we used Ubers to get to where we needed to go in short order. Here’s where those Ubers took us.
Downtown Charleston Historical Walking Tour
This was probably the highlight of the entire trip. Our tour guide, named Dennis Mardis, was a fun, engaging guide with a wealth of knowledge. We booked the tour through this Viator listing for about $27 per person.
The tour weaved throughout the downtown Charleston area. It included stops in historic churches, theaters, and parks along the way.
You can’t do a southern city history tour without broaching the subject of slavery, and our guide Dennis couldn’t have been more informative and tactful about the topic. Part of the tour included this stop outside a former slave mart – now a converted museum. During the stop, Dennis went straight at the issue, explaining the historical significance and how he holds space for both the city he loves and its atrocities.
I was interested to see how this part of Charleston’s history would be handled by local guides and was impressed by Dennis and this tour.
The walking tour then meandered down to Waterfront Park, a place created by former mayor Joe Riley who said nobody should have to pay to use Charleston’s coastline. Mayor Riley’s accomplishments (making Charleston a tourist destination chief among them) were main feature of Dennis’s tour.
Finally, the tour concluded in front of Charleston’s famed Rainbow Row of colorful houses in the city’s downtown.
I could not recommend this tour enough. It might be the best $27 you spend in Charleston. I’d do this tour on your first day if you can.
Fort Sumter National Monument
Fort Sumter National Monument is about a 30-minute ferry ride from downtown Charleston. You can only visit the fort from this ferry that makes two roundtrips per day – once in the morning and once at night.
The boat ride is an easy one through the Charleston harbor. As you travel there, a guide gives you a full rundown of the history of the island over the boat’s loudspeakers. There’s a small cafe and bathrooms on board, too.
Note: There are no bathrooms on Sumter, so the boat is all you got. There are no here are no trash cans at the fort either, so be sure to pack out all your trash.
You arrive at a dock outside the fort’s walls and walk in from there.
Inside the fort, you have your run of the place. From old fortress walls, to retired cannons, and even a small museum (and gift shop, of course), there’s plenty to do in the 90-ish minutes you’re allowed in the fort.
Before you’re set free, there’s a flag raising ceremony (or a flag lowering ceremony if you take the afternoon visit), and they ask for volunteers to help with the ceremony each time. Thrifty Traveler Co-Founder Jared raised his hand to help raise the flag on the sunny morning we spent at the fort.
Fort Sumter is a unique National Park Service experience that we recommend. The morning tour was the perfect way to spend a few hours on the water outside Charleston. For history buffs, it’s a can’t miss activity.
Coastal Boat Tour
Do yourself a favor and book something with Charleston Outdoor Adventures while you’re in Charleston, too. Located on Bowens Island, about a 20-minute drive or Uber from the city, this company offers an array of tours to help you experience the Carolina coast. You can book tours ranging from an hour-long kayak rental, to a 90-minute Outer Banks (a popular Netflix series) Filming Location Tour, to a five-hour shark tooth and fossil hunting tour, and everything in between.
For our adventure, we chose a 90-minute Coastal History Tour. The skiff tour took us all around the area, showing off the beautiful, grassy coastline and explaining the history behind every island we saw.
The speedy skiff took us out toward the Morris Island Lighthouse, too, giving us this iconic view.
No historical coastline tour is complete without…dolphins!
Over the course of 90 minutes in these channels and coves, we saw dozens of dolphins. We saw some looking for food near a popular fish shack and we saw some breaching and playing just feet from our boat.
The dolphins were spectacular. I’ve never seen so many up close. There are dolphin-focused tours offered through Charleston Outdoor Adventures, but I think we got a little extra bang for our buck by booking the historical tour that featured no shortage of dolphins.
Folly Beach
After our boat tour off Bowens Island, it was only a few more minutes down the road to the famous Folly Beach.
The intimate beach town highlighted by this sprawling, sandy spot and a long pier out into the ocean is another great place to spend a day or a half- day.
For our trip, we spent an afternoon along the pier and then hit a couple of places afterward for food and drinks. Our first stop was this cool, backyard Caribbean bar called Chico Feo. It was a cool shady spot after spending the day in the sun with good beer and great tacos.
After that, we stopped for some (many?) drinks at Taco Boy, a larger restaurant with a wraparound patio. The restaurant was in the midst of a shoulder-season menu changeover, so we didn’t get the full experience, but the margarita(s) were tremendous.
What We Ate & Drank in Charleston
Short answer: A lot.
We already highlighted where we went in Folly Beach in the section above, but there were no shortage of memorable eats around the city, too.
While we spent a few hours working each morning, we ordered in Holey City Bagels, which were a big hit among our team.
And we’re not ashamed to admit that our first stop immediately after landing at CHS Airport was to the nearest Waffle House. (We northerners don’t get to experience cuisine like this very often.)
Our first night, we tried out a barbecue place called Lewis Barbecue, and we hit a home run. There are no reservations at this spot, and you get in line and then build a tray, pay, and you’re off to the bar, booths, or picnic tables under the tent outside. If you ask, they might even let you sample some of the smoked meat first.
And if you build a tray like one of my colleagues did, it’s a sublime barbecue meal…
From the tables, you can see chefs inside slow-smoking the next day’s meats in its warehouse of smokers.
Lewis gets the Thrifty Traveler seal of approval, especially for a big group looking for some comfort food in Charleston. But I don’t think it was our best overall meal. That distinction goes to Leon’s Fine Poultry & Oyster Shop.
Fried chicken and oysters. Need we say more?
We paired some sparkling wines with oysters, had shrimp in so many ways I can’t even remember, and then split a massive fried chicken platter amongst the table. It was so good, I failed to take a single photo of the table!
Where We Stayed
While your lodging options are plentiful in Charleston, we stayed at two Airbnbs that were perfect for big groups within a few blocks of each other in the Cannonborough/Elliotborough neighborhood.
This modern gem called Brooke Haven was classy and updated while our other spot called Downtown Charleston Beauty was spacious and historic. Both were excellent places to work, stay, and play during our trip.
There is a best place to stay in Charleston, though, and that’s at the Wentworth Mansion.
A few months ago, we sent a Thrifty Traveler Premium Hotel Alert for the Wentworth Mansion, and we’ve been thinking about it ever since.
For just 100,000 Hilton points per night, you could book a night at this 21-room boutique hotel – part of the Small Luxury Hotels of the World collection. These rooms are typically north of $700 per night or more.
Putting our whole team up in the Wentworth would have been too cost prohibitive, but if I returned for a trip with just myself or my family someday, it’s high on my list of places to stay.
Bottom Line: Would We Go Back?
Yes we would! Charleston is a perfect weekend-length trip for a group of any size.
Perfect weather, a few excellent tours, and memories of barbecue, oysters, and waffles will keep Charleston on our minds for years to come.
Lead Operations Manager Erica Kamroswki contributed to this story.
Photos taken by Amber Leick.
