A Long Weekend of Southern Charm in Charleston, South Carolina

After several days exploring the stunning fall colours and mountain landscapes of North Carolina, we made our way south toward the coast for a complete change of scenery. Mark had visited Charleston with his family a few years ago and had many good things to say about it, so when we started researching things to do in Charleston for our own trip, I was excited to finally experience this city for myself.

The drive from Cherokee took us through changing landscapes as the mountains gradually gave way to the low country, and by the time we arrived in Charleston, we were ready to immerse ourselves in a completely different kind of beauty.

We were meeting Mark’s parents, who had taken the Amtrak train down and arrived earlier that same day. With three full days ahead of us, we had plenty of time to explore the best things to do in the city, from the iconic Rainbow Row to hidden gems we’d discover along the way.

Where We Stayed: The Charlestonian

For our Charleston base, we’d booked The Charlestonian, a beautiful three-bedroom property right in the Historical District. The location was absolutely ideal, placing us within easy walking distance of almost everything we wanted to see and do. While there were occasional noise issues from the adjoining apartment, the boutique stay was a pleasant balance between Southern history and modern comfort.

After settling in and catching up with Mark’s parents about their train journey, we were ready to stretch our legs and find some dinner. We didn’t want anything too formal for our first night – just good food and a relaxed atmosphere. So we headed to Moe’s Crosstown Tavern for wings and drinks.

First Evening: Getting Our Bearings

Moe’s turned out to be a great stop for the evening. The wings were good, the drinks were cold, and the whole vibe was laid-back and welcoming. It looked like the kind of spot where you can tell locals genuinely enjoy hanging out, which is always a good sign.

After our meal, we got an Uber to Waterfront Park. There, we walked along the Charleston Harbour and Cooper River, stopping briefly to see the iconic Pineapple Fountain at night.

We headed back to the hotel via King Street, knowing we would return the next morning to experience it in the daylight. Along the way, Benny Ravello’s caught our eye, and it felt only right to end the evening with a slice of pizza.

Day Two: Bagels, Markets, and Rainbow Row

The next day, we started our wanderings the way any good day should start – with exceptional bagels. We found Holey City Bagels close to our accommodation and decided to try it out. The bagels were phenomenal, and this place became our breakfast spot for the rest of the trip, which should tell you everything you need to know about how good they were.

With satisfied appetites, we set off toward the Charleston City Market. The walk itself was a pleasure. One of the best things to do in Charleston is simply stroll through the historic streets.

The Charleston City Market is one of those quintessential experiences you can’t skip when visiting. This historic market has been operating since the early 1800s, and walking through it feels like stepping into Charleston’s living history. We wandered through the long, covered market halls, browsing everything from sweetgrass baskets (a traditional Lowcountry craft) to local artwork, jewellery, and all manner of souvenirs.

From the market, we made our way toward one of Charleston’s most photographed streets – Rainbow Row. If you’ve ever seen pictures of Charleston, you’ve probably seen Rainbow Row – that iconic stretch of thirteen colourful historic houses in pastel shades of pink, yellow, blue, and green.

The houses date back to the 1700s, and they were painted in these distinctive colours in the 1930s and 40s as part of a restoration effort. Now they’re one of Charleston’s most beloved landmarks.

We continued wandering, letting ourselves get pleasantly lost in Charleston’s historic district and back streets. We passed several stunning houses and churches too, and I learnt that Charleston is sometimes called the “Holy City” because of its many historic churches and the religious tolerance that characterised its early history. The spires and steeples create such a distinctive skyline, and many of these churches are architectural masterpieces in their own right.

Eventually, all that walking warranted a treat, so we stopped at Kilwins for ice cream and fudge, and later at The Fudgery for a milkshake.

An Evening of Fine Dining and Jazz

For dinner, we made reservations at Hall’s Chophouse, a premier steakhouse often listed among the best restaurants in Charleston. It’s known for its exceptional service, great food, and genuine Southern hospitality, and we definitely experienced that during our meal. I loved everything from the way the dishes were presented to the attentive service, especially the fact that one of the owners stopped by our table to greet us.

But the evening wasn’t over yet. On our walk back to the hotel, we made a spontaneous decision to find somewhere with live music. Luckily, Forte Jazz Lounge was close by. We grabbed tickets and spent a couple of hours enjoying incredible live performances.

Ending the day with live jazz in Charleston felt like the perfect way to wrap things up.

Day Three: More Bagels and Final Explorations

On our last full day in Charleston, Mark and I woke up early to wander the city and take a few photos. We spent the morning strolling around the harbour once again, never getting tired of the views across the water.

When we returned, his parents had picked up breakfast from, you guessed it, Holey City Bagels, and we enjoyed it on the porch of our historic home.

The rest of the day was spent on more leisurely exploration, including some attempted shopping on King Street, which I loved thanks to how friendly and helpful all the shop attendants were.

For our final dinner, we ventured out to Johns Island to Wild Olive Restaurant. The drive itself was nice. Getting out of downtown and seeing more of the Charleston area. Wild Olive specialises in Italian cuisine with Southern influences, and it was a wonderful meal to end our trip. The flavours were bright and fresh, the atmosphere was warm and inviting, and it felt like the perfect way to end our Charleston experience.

Things to Do in Charleston SC: Reflections on Southern Charm

Looking back on our long weekend in Charleston, the city truly lives up to its reputation for Southern charm. It is beautiful, historic, and endlessly photogenic. The food is exceptional, the architecture is stunning, and the warmth and politeness of the people we met made the experience feel especially memorable.

Visiting Charleston in November also could not have been better timed. We were lucky to have clear skies and comfortable temperatures that made walking around the city a pleasure, without the heavy heat and humidity Charleston is known for in the summer. If you have flexibility when planning your trip, fall is a great choice. The city still feels lively, but without peak summer crowds, and the weather makes it easy to spend hours exploring on foot.

And exploring on foot is really the best way to experience Charleston. The historic district is eminently walkable, with something interesting to see around every corner. Unlike cities where major attractions are spread far apart, Charleston’s highlights are concentrated in a relatively compact area. We easily walked several miles each day without it ever feeling like a chore because the scenery was constantly changing and engaging. The time spent with family made this trip even more special.

Practical Tips for Your 3 Days in Charleston Itinerary

If you’re planning your own Charleston getaway, here are a few things I learned:

Accommodation location matters: Staying in downtown Charleston, as we did at The Charlestonian, meant we could walk almost everywhere. This not only saved money on rideshares and parking but also allowed us to experience the city more intimately. You see and notice so much more when you’re on foot rather than in a car.

Start your days early: Charleston gets busier as the day goes on, particularly in popular areas like Rainbow Row and the City Market. We found that morning explorations were more peaceful and allowed for better photos without crowds of people in the background. The Pineapple Fountain in Charleston is especially beautiful at sunrise if you’re an early riser.

Make dining reservations: For the best restaurants in Charleston, like Hall’s Chophouse, reservations are essential, especially on weekends. Charleston’s food scene is popular for good reason, and the best spots fill up quickly.

Consider evening entertainment: While we loved the jazz at Forte, Charleston ghost tours are another popular evening activity. The city’s long history makes for some fascinating and spooky stories, though we saved that experience for a future visit.

Check the Charleston SC weather: November is ideal, but whenever you visit, check forecasts and pack layers. The weather can be variable, and you want to be comfortable during all that walking.

Explore beyond the obvious: While Rainbow Row and the Pineapple Fountain are must-sees, some of our favourite moments came from more spontaneous discoveries. A beautiful church we stumbled upon, a quiet street with perfectly preserved houses, and a park we hadn’t planned to visit. Don’t forget to wander down Broad Street and the surrounding historic streets, where you’ll find stunning architecture and fewer crowds.

Embrace the leisurely pace: This isn’t a city for rushing through with a packed itinerary. Charleston rewards those who slow down, wander, and let themselves be surprised by hidden gardens, unexpected architectural details, and chance encounters. Some of our best moments came from simply wandering without a specific destination in mind.

The Sum Up…

For anyone considering a visit to Charleston, I cannot recommend it enough. Whether you love history, food, architecture, or simply beautiful places with real character, Charleston truly delivers. There is no shortage of things to do over a long weekend, from exploring Rainbow Row and shopping along King Street to enjoying standout restaurants or wandering through parks and historic streets. It is the kind of city whose charm lingers long after you leave.

Have you visited Charleston? I’d love to hear about your favourite spots and experiences in this beautiful Southern city!