In January of this year (2026), I headed out on I-95 Northbound. My destination? St. Augustine for the night and then Charleston, South Carolina.
One of my all-time favorite TV shows is the Netflix series, The OBX. It’s filmed in Charleston, but it’s set in North Carolina. The show highlights the natural beauty of the Low Country and its boating and beach culture. It made me want to visit the area.
So, a few days after the New Year, I packed my car and headed North to explore all Charleston, or The Holy City as it’s called, had to offer. In this food & travel guide, I’ll break down what I did, where I ate, and where I stayed while in town, so you can use it to plan an awesome trip of your own!
Best Things To See, Eat, and Do in Charleston
What To Do in Charleston
Charleston is a port city in South Carolina founded in 1670. It’s known for cobblestone streets, Low Country Cuisine, and Civil War history. Whether you love history, boating, or great food, this coastal city has plenty to do.
The Battery
The Battery is a 1.2-mile walking trail (promenade) around Charleston. It was constructed in the early 1800s before the Civil War to serve as a protective sea wall.
Today, the battery begins roughly at the Pinapple Fountain near Queen Street and ends at Tradd Street. It is a popular spot for locals and tourists. It offers gorgeous views of the Ashley River, Cooper River, Charleston Harbor, and historic homes.
I started at Waterfront Park Pier and walked down to Tradd and then back to Kinstreet, where my hotel was. I was able to take in the sights and sounds of Charleston as well as stop at Rainbow Row, White Point Garden, and the John Rutledge House along the way.
Don’t forget to pack your walking shoes because this trail is an absolute must-do while in town.
Pineapple Fountain at Waterfront Park
Among the eight acres of Riley Waterfront Park sits the gorgeous Pineapple Water Fountain. This iconic symbol of Charleston is a free tourist attraction and a beloved part of the city by locals.
In the past, pineapples were hard to acquire and quite expensive as they were grown in South America. Therefore, when sailors arrived in port, they would cut a pineapple and invite their neighbors to come by and enjoy one along with a meal or drinks and swap stories from faraway lands.
Over time, pineapples became a symbol of sailors’ safe return, wealth, and hospitality. They can be seen throughout people’s homes and in public architecture and decor in Chucktown.
Rainbow Row
Rainbow Row is another lovely free Charleston attraction. It’s the name given to a row of 13 colorful pastel houses near The Battery.
In 1931, a section of these houses was purchased after reaching near slum-like conditions. They were restored and painted pink to align with a Colonial Caribbean color scheme. Several of the neighboring houses were built, and the owners followed suit, creating the rainbow of pastel colors.
Rainbow Row is one of the most photographed areas of Charleston and is great for group and solo photo ops.
Fort Sumter
While walking The Battery, I randomly decided to visit Fort Sumter upon seeing it out in the Charleston Bay.
Fort Sumter, not to be confused with Fort Sumner in New Mexico, is considered a National Historic Park that sits at the mouth of the Charleston Harbour.
Fort Sumter was constructed on a sandbar in 1829. It’s a response to the War of 1812, which highlighted the exposed coastline that left the city vulnerable to naval attacks. It’s most historically significant for the Battle of Fort Sumter, which began the Civil War on April 12, 1861.
The Fort was never completed due to title and construction issues; however, it remains today as a destination for visitors. I took the ferry boat from the Fort Sumter visitors center located inside Liberty Square park. It took us about an hour to sail both ways, and my group had about an hour to explore the Fort and the gift shop.
Overall, I had a great time, and this experience was worth the money. I enjoyed taking in the picturesque Charleston views from the boat as well as exploring the Sumter. For me, it was hard to wrap my brain around the fact that a battle with cannons and guns took place on a random sandbar there before cell phones and computers, and the boats we have today.
If you’re looking for something unique to do while in town, definitely add this experience to your bucket list. I booked my ticket on Viator, but you can purchase a ticket at the visitors center before you board the ferry. The ferry was very full when I arrived, so I would purchase tickets before you go.
Shem Creek (Mt. Pleasant)
Just over the Arthur Ravenel Jr. Bridge from downtown Charleston sits the suburban town of Mount. Pleasant. It offers gorgeous views of the Charleston Harbour, downtown Charleston, and Shem Creek, which cuts through it.
Along the creek, there is a boardwalk where visitors can take a stroll and take in the marsh and ocean views. Along the boardwalk is also a collection of popular restaurants and bars accessible from the main boardwalk.
I was excited to visit Shem Creek not only to take in the gorgeous views, but because The Outerbanks (OBX), is quite frequently filmed there.
I instantly recognized some of the filming spots as well as some of the boats, including a fishing boat named Playboy! It was really neat to see in person. After exploring, I tried to have lunch at Saltwater Cowboys and try their brisket nachos and fried okra, but they were closed. So, that’s how I ended up at Page’s Okra Grill.
While I didn’t see John B and the Pogue gang, exploring Mount Pleasant and Shem Creek was a great way to spend a half day.
Daniel Island
My housesit in Charleston was actually situated on Daniel Island, about 14 miles outside of Charleston proper. The area had more of a suburban community feel with many nature trails spanning the entire island.
One of my favorite trails started at Smythe Park and snaked all the way to Daniel Island Waterfront Park for about 1.5 miles. It featured spectacular views of the marsh, gorgeous homes, and the Wando River.
When you get to Daniel Island Waterfront Park, there are a few cafes and restaurants that serve coffee, lunch, and dinner. I didn’t try any of them, but they have great Google reviews and seem like a solid spot for coffee or a sandwich.
The trails on Daniel Island are very dog and family-friendly, which is perfect if you’re looking to take in the serene South Carolina landscape away from the hustle and bustle of downtown Charleston.
Angel Oak Tree
No trip to Charleston is complete without stopping by to see the Angel Oak, located on Johns Island, approximately 12 miles outside of town.
Angel Oak is a sprawling 400-500-year-old Live Oak tree that stands about 66.5 feet tall and 28 ft in circumference. The tree gets its name from local folklore stories that say enslaved people were seen to appear as angels near the tree throughout history.
I was absolutely amazed at how expansive the Angel Oak was. It is by far the biggest tree I’ve ever seen, and it was totally worth the drive to see it and hang out under its shade for a bit. I would have loved to have taken a picnic and sat under the shade—maybe next time!
Angel Oak is free to visit, although donations are accepted.
More Things To Do In Charleston
From exploring the Battery and Fort Sumter to indulging in low-country cuisine and history, there’s a lot to do in Charleston. Check out these tours offered by Viator. When I travel, I either book through the cruise ship directly or through Viator.
What to Eat and Drink in Charleston
Low Country food draws inspiration from traditional African flavors and the available seafood in the area. It’s similar to Cajun cuisine you would find in New Orleans. Typically, low country cuisine is referred to as the regional food from Pawleys Island, South Carolina, all the way to the Savannah River at the Georgia state line. When I think of Southern comfort food, I think of the food in the Carolinas as well as Giorgia.
Paige’s Okra Grill (Mt. Pleasant)
Just across the Ravenel Bridge from Charleston sits Page’s Okra Grill in Mt. Pleasant. It’s low-country cooking at its finest, serving up everything from fried green tomatoes and chicken and waffles to crab cakes and mac n cheese.
I was so hungry when I arrived at Page’s, after walking Shem Creek and all over Mt. Pleasant beforehand. So, when I saw the PBT — a fried green tomato, pecan-smoked bacon, and pimento cheese sandwich- I knew I had to have it!
There’s a reason this sandwich was featured on the Travel Channel, as it can only be described as heaven in between two buttery Texas toasts. The first bite was a religious experience. I tasted the creaminess of the pimento, plus the crunch of the fried green tomato with the savoryness of the bacon. It healed something inside of me, that’s how damn good it was.
I had the sandwich on Monday and thought about it all week, so I indulged again on Thursday as I was heading out of town.
If you’re in Charleston, obviously, Page’s is one place I think you should absolutely dine at. Get the fried okra with a side of ranch and thank me later!
Prophet Coffee (North Charleston)
Tucked away in North Charleston is Prophet Coffee. It was conveniently located within walking distance from a hotel I stayed at on my second night in town.
The building, location, and overall vibe reminded me of East Austin, so I naturally felt right at home. I got a honey oat cold brew (or something like that), and it was quite tasty with balanced notes of coffee, oat milk, and honey.
The best part? This coffee was right at $6, making it at least $3 cheaper than the average coffee here in South Florida!
Inside, there was plenty of space to sit and work, and plenty of parking in the front. I had grand plans to work remotely there one day, but it didn’t happen. Perhaps next time!
Carolina Cider Company (Yemassee)
Ok, so technically, this Carline Cider Company is about an hour outside Charleston; however, I was heading down Highway 17 on the way to Charleston and blew right past it. It was about 9 am and slightly drizzly, and the patio lights caught my eye. Then, I read coffee and cider on the store signs and did a quick U-turn.
I left St. Augustine at 5 am that same morning, and I definitely needed more caffeine and a sweet treat. Plus, I love to buy things like local honey and coffee when I travel to bring back home and enjoy, so I thought this would be a great place to stop, stretch my legs, and shop for a few provisions.
I got out of my car and stepped into the cutest and possibly the smallest little coffee shop I’ve ever been to on the side of the road. I opted for an iced matcha since the barista said their blend was fantastic. While the barista was whipping up my latte, I went into the main store to browse.
Jars of pickles, pickled vegetables, seasoning mixes, jams, and honey met my eyes. It was hard not to buy one of everything, but I settled on some local honey and a cider donut from the glass case. Autumnal flavors exploded with each warm, delicious bite of the donut. My taste buds were happy to sample something not commonly available, and the mix of carbs, sugar, and caffeine gave me the second wind I needed to finish the trek into Charleston.
Make sure to stop by one of the three Carolina Cider locations while in the Charleston area—they’re worth the drive!
Revival (Inside the Vendue Hotel)
Revival is a swanky, dimly lit Southern eatery centered on dishes from Charleston’s rich culinary history. I had seen Brussels sprouts and charred okra on the online menu, so I was convinced before I stepped through the door.
The first day I was in Charleston, I walked all over The Battery and Fort Sumter, a total of about 25,000 steps. Needless to say, when I got back to my hotel, The Vendue, I was absolutely famished. Thankfully, the hostess let me in with black leggings and a white puffy vest, which I’m sure is far from dress code.
It was Sunday evening and chilly, so I ordered the Brussels sprouts and roasted potatoes since they were out of the okra to start with. They were both flavorful and comforting after my long day. For my main course, I went with the butternut gnocchi, which was as warm and rich as you’d expect it to be.
If you’re looking to have a nice Southern dinner near The Battery, definitely stop by Revival. Pro tip: after dinner, you can wander the art gallery of the Vendue Hotel.
Best Places to Stay in Charleston
Surprisingly, Charleston is kind of spread out. Downtown is almost on a peninsula, while Mount Pleasant and North Charleston are separated by a series of bridges and bodies of water. Therefore, there are many different parts of Charleston to stay and explore.
Vendue Art Hotel
For my first night in Charleston, I knew I wanted to stay close to downtown near The Battery and Charleston Waterfront. Luckily, I was in town after the major holiday traffic and managed to get a decent deal on the Vendue.
The Vendue is a 4-star property within walking distance to all the major Charleston attractions like Rainbow Row, King Street, Broad Street, and White Point Garden. Instead of a traditional hotel lobby, the Vendue features a bright red interior and art gallery with over 200 pieces of original art, which guests can explore at any time.
In addition to this unexpected feature, the hotel itself is a historic building with an avant-garde boutique feel. The rooms are older, but quaint, and even feature multiple art pieces.
I had a fabulous stay at this hotel and would definitely recommend staying here if you have not explored downtown Charleston or want to be able to walk to all the points of interest, restaurants, and attractions.
Pro tip: The only caveat here is that parking is pricey. The hotel offers valet at $50 per night. I made the mistake of parking my car in the public lot in the back of the hotel, thinking it was going to be cheaper. It was indeed NOT cheaper, and I was charged $70 per 24 hours. Normally, I would be too shocked to pay that much, but I was ready to drink a complimentary mimosa and go sightseeing, so I stayed in that lot. I also brought my bike with me and wanted to bike downtown. However, it’s not very bikeable. Walking around, I discovered that one block away was a public parking garage that only charged $25 per day. I would suggest giving your wallet a break and parking there instead.
Circulo Hotel
In between, I needed a place to stay and found Circulo in North Charleston. Circulo is a keyless and front-desk-less hotel with a chic boutique vibe.
What attracted me was its 4-star property rating and pictures of large, spacious rooms with clean, modern lines and minimal decoration. Then I noticed its phenomenal price of just at $100 per night. I immediately called the hotel, thinking it was too good to be true!
I ended up staying two nights at the Circulo, and it was every bit as fabulous as the online pictures. And despite the up-and-coming neighborhood aesthetic, I felt overall safe and felt good about leaving my car in one of the few covered parking spots at the bottom of the building.
A perk of staying here is that I was given vouchers for $2 off at Prophet Coffee, the coffee shop next door. What’s better than waking up in a beautiful hotel and then walking to a top-rated neighborhood coffee shop?
Trusted Housesitters
I have been doing Trusted Housesitters on and off since 2023. My first sit was in Freeport, Bahamas, for nearly a month with four giant dogs. While that trip was interesting in a few not-so-great ways, I’ve learned a lot from that experience and have had much better stays. You can read more about my Bahama Housitting experience here.
After my Bahamas trip, I took a break from housesitting for a while. For my South Carolina trip, I knew I wanted to stay for at least a week, if not longer, so I reactivated my account and set out to find a few places to housesit so I could experience Charleston for longer than a weekend.
I was able to find not only a stay in Charleston but also just South, in Beaufort. My goal was to also get a sit in Hilton Head Island, but I decided last minute that a stay in Hilton Head would take me away from home longer than two weeks, and the timing just didn’t feel right. So, after nearly two weeks in South Carolina, I headed back home to Florida. I plan on checking out Hilton Head next for sure!
Want to try Trusted Housesitters? Use my link to get 25% off a membership.
Is Charleston Safe?
Charleston is generally considered a safe city, especially in the historic district and popular areas like King Street and some beaches. Crime is a bit higher in areas like North Charleston, but visitors should take normal precautions
Free Things to Do in Charleston
- Rainbow row
- The Battery
- Walk King Street (The Historic District)
- Explore Shem Creek (Mt. Pleasant)
- Check out the Angel Oak
What To Pack For Charleston
My goal for this trip was to enjoy the Carolina outdoors, so I packed some of my favorite travel essentials like my Yeti cooler, Yeti cup, and a suitcase full of athletic wear in packing cubes.
I also took my bike, which I ended up not getting to use much. Downtown Charleston wasn’t very bike-friendly as I thought it would be, as bikes are not allowed on The Battery. However, there are a few bike-friendly trails outside of town that I would like to explore, like the Spanish Moss Trail, the next time I’m in town.
Tell Me Everything!
What are your favorite things to see, do, or eat in Charleston?
*Disclosure: I only recommend products I try myself, and all opinions expressed here are my own. I am a Viator and Expedia partner. This post may contain affiliate links that, at no additional cost to you, I may earn a small commission. Thanks for supporting the Eat Well. Adventure Often. blog!