A Relaxed Charleston Getaway: The Perfect Mix of History, Happy Hours, and Coastal Charm
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Charleston had been on my travel wish list for years, and after spending four days exploring the city, I can confidently say it lived up to the hype. In fact, after our recent trip, I have already begun planning how to go back for another Charleston getaway – and next time, I’m bringing the rest of the family!
What surprised me most wasn’t the historic homes or famous landmarks—it was how easy Charleston is to enjoy at a slower pace. We spent our days wandering cobblestone streets, learning about the city’s fascinating history on a walking tour, enjoying leisurely happy hours, and taking in rooftop views of church steeples and the harbor. We mixed in a half-day at Shem Creek, an afternoon at Folly Beach, and plenty of incredible meals along the way.
If you’re looking for a destination that combines history, great food, waterfront views, and just enough beach time, Charleston delivers. Here’s how we spent four days enjoying the perfect mix of history, happy hours, and coastal charm.
Where We Stayed in Charleston
As this was my first visit to Charleston, I really didn’t know where I wanted to stay. I knew I wanted the ability to walk most places, and I thought I’d enjoy something a little bit historic while still being comfortable.
Since I was unsure of what part of town I’d like best, we decided to do a split stay. We spent two nights at the Lodge Alley in the historic district, and two nights at King 583 near the more upscale shopping, bars, and restaurants.
Although the two locations were only a mile or so apart (both were downtown), the stays felt very different. The first two nights at Lodge Alley were the perfect introduction to iconic Charleston sights, such as the Pineapple Fountain and the Charleston Market. Our second stay centered around shopping and restaurants and felt a bit more modern.
One of my favorite parts of staying downtown was that we rarely needed the car. Most days we simply wandered from restaurant to rooftop bar to historic site, discovering little side streets, gardens, and shops along the way.
What would I do differently next time? Although I liked both options, next time I’d opt to stay the whole time at Lodge Alley – most of the restaurants we liked best were near that location, and I liked being able to walk down to the waterfront easily. That being said, if only King 583 was available (or the Hyatt across the street from it), I’d happily stay there instead.
Charleston Trip at a Glance
- Length: 4 Days
- Best For: Couples, Girlfriend Getaways, Empty Nesters, Families w/Older Kids
- Highlights: Walking Tour, Rooftop Bars, Folly Beach, Shem Creek
- Favorite Restaurant: High Cotton
- Favorite Rooftop: Vendue
- Best Day Trip: Shem Creek
- Would We Return? Absolutely
Why We Loved Charleston
Our visit to Charleston has easily become one of my favorite recent trips! I loved the history, the walkability, the incredible restaurant scene, and so much more about this wonderful city.
We enjoyed rooftop bars, live music, gorgeous architecture, and even an afternoon at the beach. What else could I ask for in a long-weekend getaway? The city had such a rich history to it, but didn’t feel like a “museum” city – it felt warm, welcoming, and FUN!
We also discovered early on that Charleston has an incredible happy hour scene. Since we usually prefer sharing appetizers over ordering huge dinners, it ended up being the perfect way to experience more restaurants without feeling rushed.
So, what exactly did we do? Let me take you through our 4-day itinerary – perfect to give you a taste of the city as we had, but selective enough to leave you plenty of things to do on your return visit.
Day 1: Southern Hospitality and Rooftop Views
We arrived early afternoon, just in time to check into our hotel, hit up the local Target for some snacks, drinks, and breakfast items, and then ease into happy hour. Since our first two nights were in the historic district, we were immediately immersed in Charleston’s historic charm.
Happy Hour at Amen Street Fish & Raw Bar
Of all the happy hours in this part of town we experienced (and there were quite a few), we liked Amen Street Fish & Raw Bar the best. In fact, we liked it so much we went back on Day 2 for another drink! Sitting at the bar, chatting with the bartender and enjoying fresh oysters (we watched them shuck them right in front of us) and some amazing fried green tomatoes was an excellent start to our Charleston adventure.
Amen Street Fish & Raw Bar, 205 E. Bay, Charleston, SC
Charleston City Market
Charleston Market is an interesting historic yet commercial site. Opening in the 1790’s, it’s one of the oldest public markets in the United States. It is also much bigger than I expected, but surprisingly, we walked through it fairly quickly.
While we didn’t do much shopping ourselves, it was fun browsing the handmade sweetgrass baskets and local artwork. If you’re someone who likes collecting ornaments, magnets, or locally made gifts while traveling, you’ll probably spend more time here than we did.
Charleston City Market, 188 Meeting Street, Charleston, SC
Walked to the Charleston Waterfront Park
As the afternoon turned to early evening, we walked down to the waterfront to check out the famous Pineapple Fountain. There were plenty of families and couples enjoying the gorgeous weather and the lovely park.
It was peaceful to see the many boats on the water, feel the breeze off the harbor, and even hear the clip-clopping of the frequent horse-drawn carriage tours checking out the waterfront and nearby Rainbow Row.
Charleston Waterfront Park, Concord Street, Charleston, SC
High Cotton & Henry’s for Live Music
To top off our night, we headed back to our lodgings and hit both High Cotton (connected to our hotel) and Henry’s down the street for live music and drinks. Both were terrific spots with great vibes, yummy drinks, and just a fun atmosphere.
High Cotton, 199 Bay St. Charleston, SC
Henry’s, 54 N. Market St. Charleston, SC
Day 2: Discovering Charleston’s History on Foot
Take a Walking Tour
One of my favorite things to do in a new city is to take a walking or bus tour at the beginning of the trip. It’s an easy way to learn a little bit more about the city, get a good feel for the layout, and, if you are lucky, discover some hidden details you would have missed otherwise.
Since Charleston is well-known for its history, we picked a historical walking tour for our first full morning, and it was a hit! It was super affordable, our guide was very knowledgeable, and we learned a lot. The tour started a short distance from our hotel, and we explored quite a bit of the historical district – some of it really reminded me of New Orleans (another city I love). From architecture to history to suggestions for future adventures in Charleston, we experienced a lot.
I would highly recommend this as a first tour when visiting Charleston, and I am very glad we did it – it was one of the highlights of our trip. Next time I visit, I’ve got my eye on a fun ghost tour like this one – especially if I bring one of the kids along!
Afternoon Happy Hour Break
By the time our walking tour ended, it was early afternoon, and after a quick rest at our hotel (last night was a late one), we headed back out for more happy hours. Charleston is chock-full of terrific happy hours, so exploring them quickly became one of our favorite afternoon activities. I’m not sure we saved much money, but we sure had fun trying a lot of different restaurants.
Drinks at The Vendue Rooftop
One of our favorite stops on today’s happy hour tour was The Rooftop at The Vendue. If there is a rooftop bar, we are probably going, so this was a no-brainer on today’s happy hour tour. Although we discovered several rooftop bars during our visit, I was a big fan of this one. First of all, it is located in a very cool boutique hotel called The Vendue.
Before you even visit the rooftop bar, you should definitely spend a little time in the lobby of the hotel checking out the unique artwork. Although there were many interesting pieces, I especially liked one that had a bunch of Viewmasters to look through – and they spelled out “Look” if you stood back. Super cool.
The bar has a bit of a bougie vibe (love that!) and excellent views of the water and downtown. It was a short walk from our hotel, and although we didn’t get any food, we did enjoy a few craft cocktails. Be sure to walk all the way to the top deck to get the best view.
The Rooftop at The Vendue, 19 Vendue Range, Charleston, SC
Back to High Cotton for Dinner
After drinks, we headed back towards our hotel and High Cotton for a light dinner, cocktails, and live music. It was the perfect end to a perfect Charleston day!
Day 3: Sunshine, Sand, and Folly Beach
Today was the day we moved hotels, so knowing we’d be homeless for at least part of the day, it was the perfect time to drive a little bit out of the city and check out Folly Beach.
Morning Drive to Folly Beach
What a lovely surprise! Just about a half-hour outside of the city, Folly Beach has total beach vacation vibes and lovely views of the ocean! There is only a small downtown, but we found parking easily enough on the street and spent an hour browsing the beach shops – they were full of typical beach vacation stuff like sweatshirts, T-shirts, keychains, shot glasses, etc.
Folly Beach has a laid-back, slightly quirky vibe that felt very different from Charleston’s polished historic district. It was exactly the change of pace we wanted after two days of city living.
Drinks at Pinky’s
We stopped at Pinky’s, grabbed a table overlooking the ocean (heaven), and ordered some margaritas, chips, and dips. It was the perfect casual, oceanfront location.
Connected to the largest hotel on the beach, Pinky’s has a laid-back atmosphere, plenty of seating (most with ocean views), and a variety of appetizers, pizzas, cocktails, and more.
Pinky’s on the Beach, 1 Center Street, Folly Beach, SC
Relax at Folly’s Beach
After our light lunch, we walked the beach for a while, stopping to check out the pier. There was a bar where we picked up a few drinks, then walked to the end of the pier to watch the folks fishing. We saw one kid catch a small shark!
One of the things I really love about this pier is the tall Adirondack chairs you can sit on along the edge to relax and enjoy the view. We sat for quite a while with our drinks, soaking up the sun and people-watching.
Enjoy the Shopping District’s Nightlife
Since we moved hotels, we had a whole new group of restaurants and bars to check out. By Day 3, we had our happy hour routine down, so we started at a happy hour just down the block from our new hotel that multiple people had recommended.
Happy Hour at Prohibition
Prohibition is exactly the kind of old-school, cocktail bar you imagine when you hear the name. We sat at the corner of the bar and enjoyed some great cocktails and a few appetizers in the very swanky atmosphere.
The bartenders are experts at mixing drinks – we watched them make some pretty delicious-looking ones that all had a beautiful presentation. There is a spot for live music, and Prohibition is also a restaurant (with an outdoor courtyard), but we moved on because we wanted to hit a few other happy hours.
Prohibition, 547 King St. Charleston, SC
Rooftop Bar at The Nickel
Since it wasn’t dark yet, we decided to check out the Rooftop Bar at The Nickel Hotel. This was another beautiful bar with lovely city views. We started at the bar (always the best way to discover the best things to order and get a feel for a place), ordered drinks and a burrata appetizer. After a bit, we took our drinks outside to enjoy the view for a while.
The Nickel Hotel, 529 King St. Charleston, SC
Light Dinner at Indaco
After our bar hopping, we were a bit hungry, so we went to Indaco to split a delicious pizza and a salad. Indaco has a lovely selection of brick oven-fired pizzas, rustic pasta dishes, and appetizers. If you love Italian (and although we love seafood, sometimes we do want a change), this is a wonderful choice.
Indaco, 526 King St. Charleston, SC
Day 4: A Laid-Back Morning at Shem Creek
How did day 4 come so quickly? This trip has flown by!
Drive to Shem Creek
Since we get up early, after hitting the gym we decided to head back out of town to explore Shem Creek. We’d had several locals recommend it to us, and since we knew we didn’t need a whole day to shop King Street, we thought it would be a great start to the day.
We grabbed coffees to go from the hotel, and then headed across the bridge. Since it was still pretty early, we parked at the free parking lot and took off across the boardwalk. The marsh views were beautiful, and the weather was perfect for walking. We ended up chatting with a few locals (their dogs drew us in), and they gave us a great lunch recommendation!
Lunch at Saltwater Cowboys
We drove over to Saltwater Cowboys as soon as they opened at 11 (and it got busy, so we were glad we did!), and snagged a two-top right by the water. I ordered peel-and-eat shrimp (so good), and my husband got fish and chips (also amazing). Along with a few drinks, we were set for a fun early lunch.
The food was good, the atmosphere fun and vacationy, but the best part? The dolphins playing alongside the docks! We could easily watch them from our table. Apparently, Shem Creek is where a lot of the shrimp boats come and go, so the dolphins often hang out in the area – odds are very good you’ll get to see them if you visit.
Saltwater Cowboys, 130 Mill Street, Mount Pleasant, SC
One Last Charleston Evening
Back to King Street! By now, we were experts on exploring Charleston on foot, and spent quite a bit of time browsing the shops on King Street and then stopping into a few new spots for an early dinner:
Bar 167
Bar 167 ended up being another one of our favorite stops! I actually still talk about it when we share stories about our Charleston trip. It has an adorable little outdoor patio, excellent happy-hour drinks, and an AMAZING Greek platter full of olives, hummus, pita, cheese, etc. It was perfection. My husband immediately ordered oysters and thought they were some of the best he had had all week (and he had them somewhere every day). During happy hour, it was all super affordable.
Bar 167, 5 Fulton St. Charleston, SC
Burwell’s Stone Fire Grill
We were pretty full, but so many people had suggested Burwell’s Stone Fire Grill that we felt like we should check it out. As normal, we sat at the bar and decided to just split their specialty, the “hot rock”. Basically, they bring out a hot rock and a few pieces of raw meat and you cook them yourself – it was pretty fun and definitely unique! The appetizer was plenty for us to give it a try, and it was a fun “last stop” for our Charleston trip.
Burwell’s Stone Fire Grill, 14 N. Market St. Charleston, SC
One Thing We Didn’t Expect: Charleston’s Happy Hour Scene
I knew I’d love the history & architecture of Charleston, and I had heard the foodie scene was great, but I had no idea how fun the happy hour scene would be!
Because we decided to do a happy hour crawl each night instead of a full dinner, we were able to try so many more restaurants, along with plenty of different dishes. Not to mention, I’m not a big eater and will almost always pick an appetizer and a great drink over a full dinner, so happy hour is perfect!
Normally, I’d recommend happy hours as a way to save money, but honestly on this trip, we tried so many that I don’t think it was really a money-saver, but it WAS a lot of fun!
Where We Ate
I know I went through a lot over the four days, and actually there were probably at least a half dozen more restaurants and bars I didn’t mention, but here is a quick reference of our favorites.
Restaurants We’d Recommend
Best Places for Drinks
Conclusion: Is Charleston Worth Visiting?
Charleston surprised me in all the best ways. I expected beautiful homes and fascinating history. What I didn’t expect was how relaxing the trip would feel – lingering over happy hour, wandering charming streets with no real agenda, spending an afternoon at the beach, and ending each evening with live music or rooftop views.
It’s the kind of destination that makes you slow down and simply enjoy where you are. And if you’re anything like me, you’ll probably start planning your return trip before you’ve even unpacked your suitcase.
Charleston is a good choice for a long weekend, and a wonderful trip for couples. I think it would also be a fun girls trip, and my older teenagers would like it too. I think if we’d visited when the kids were younger, we would have had to branch out to find more “touristy” things to do.
A few unexpected standouts for me include Shem Creek – I will definitely visit again for another early morning walk, and our historical walking tour. If you’ve ever thought about a trip to Charleston, don’t wait – book it!
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