Charleston Charm: A Girlfriend Getaway

There’s something truly magical about Charleston in the fall — the blend of rich history, vibrant culture and unparalleled Southern hospitality. This past October, I organized a girls' trip for a group of fabulous ladies eager to explore all the best this charming city has to offer. Here’s a look into our unforgettable Charleston getaway!

Day one: Arrival and settling in

Our trip began with an evening flight from Houston, landing in Charleston to a warm coastal breeze. After a quick transfer to our rental on St. Philip Street, we arrived to a welcoming spread of pre-arranged wine and cheese. We settled in, unpacked and enjoyed a toast before exploring the charming home, perfectly located in the heart of downtown.

Day two: A taste of history and culture

Our first full day started with a private tour that took us through Charleston’s historic districts. We admired the grand mansions along The Battery, passed by Rainbow Row and marveled at some of the oldest churches in the South. Our guide shared fascinating stories about Charleston’s role in American history, bringing the city’s past to life.

Ready for a break, we headed to 82 Queen for lunch, where we dined on their signature she-crab soup and fresh garden salads in the gorgeous garden courtyard. It was the perfect light meal to fuel up for an afternoon of exploring and soaking in Charleston’s unique charm.

With our appetites satisfied, we spent the afternoon exploring on our own, starting at the Charleston City Market. We wandered through the historic market’s lively stalls, chatting with local artisans and picking up a few unique treasures to take home. From there, we set off on foot to discover more of Charleston’s iconic sites, strolling down picturesque streets lined with charming pastel houses and historic landmarks like the Four Corners of Law. Every corner seemed to have a story waiting to be uncovered, and we loved soaking in the beauty and history at our own pace.

After a late afternoon break and freshening up, we set out for the evening with cocktails at Camellias, a chic champagne bar. The sparkling drinks and lavish pink décor made it the perfect spot to unwind and snap a few fun group photos.

From there, we headed to Peninsula Grill for dinner. The restaurant’s sophisticated ambiance and beautifully plated dishes made it one of the highlights of our trip. We couldn’t leave without indulging in their famous Ultimate Coconut Cake — a decadent, towering slice that was worth every bite!

Day three: Shopping and sipping

We dedicated the day to shopping along King Street, Charleston’s premier destination for retail therapy. Known for its array of boutique shops, designer stores and charming cafes, it was a shopper’s paradise. We ducked in and out of stores, trying on everything from jewelry to dresses, and found some hidden gems to add to our wardrobes. Midday, we took a break for lunch at Magnolias on East Bay Street. The restaurant’s bright, welcoming atmosphere and refined Southern fare made it the perfect spot to savor Charleston classics like fried green tomatoes and crab cakes before heading back out for more shopping.

Dinner that evening was at High Cotton, where the highlight was definitely the truffle parmesan fries paired perfectly with a bottle of wine. Afterward, we made our way to The Charleston Place hotel bar for a nightcap, chatting late into the evening over cocktails and soaking up the vibrant atmosphere.

Day four: Historic homes and Southern steaks

We started our morning at Bodega, a local favorite known for its breakfast sandwiches and laid-back vibe. With coffee in hand, we set off for our tour of Magnolia Plantation & Gardens. The property, set just outside the city, is one of the oldest in the South. We spent the morning wandering through winding paths, taking in the moss-draped oaks, beautiful camellias and serene ponds filled with blooming water lilies.

The tour offered a peaceful escape from the city and gave us a deeper insight into Charleston’s complicated history. We even spotted a few alligators lounging along the banks, adding a little thrill to the day!

For our final night, we pulled out all the stops with a dinner at Halls Chophouse. Known for its prime steaks and Southern hospitality, Halls lived up to its reputation. The service was impeccable, and each dish, from the tender filet mignon to the rich pepper jack creamed corn skillet, was cooked to perfection, making it a dining experience we won’t soon forget.

Day five: Farewell Charleston

Our final day came too quickly with an early-morning flight back home. We packed up before dawn and headed to the airport, still reminiscing about the highlights of our trip. As we boarded, we were already talking about when we might return to experience even more of Charleston’s charm.

Charleston takeaways

Charleston is a city that effortlessly blends old-world charm with modern sophistication, making it the perfect destination for a girls' trip. From historic tours and stunning architecture to some of the best restaurants in the South, there’s something for everyone. Whether you’re a history buff, a foodie or simply in need of a stylish escape, Charleston will capture your heart — and keep you coming back for more.

Until next time, Charleston!

Charleston’s mix of rich history, fantastic food and Southern hospitality made it the perfect destination for our girls' getaway. We explored historic landmarks like The Battery and Rainbow Row, indulged in Lowcountry cuisine and enjoyed lively nightlife at chic spots like Camellias. Shopping on King Street and a serene visit to Magnolia Plantation added variety and charm, creating a memorable experience we’re already eager to repeat.

This trip report is part of our ongoing series on travel to Charleston. In need of further inspiration? Check out Caroline Heeren’s guide, Holiday Travel Guide to Charleston, SC.