Girls Getaway
Experience a relaxed and refined Charleston girls getaway with this thoughtfully planned four-day itinerary. From candle-making and wine tasting to rooftop dinners, boutique shopping, and sunset sails, every moment is designed for connection and discovery. Stay at the elegant John Rutledge House Inn®, where historic charm meets modern comfort. Whether you’re sipping cocktails under the stars, strolling through centuries-old gardens, or indulging in Southern cuisine, you’ll find the perfect mix of history, hospitality, and unforgettable memories in every day.
Thursday
- Welcome to Charleston! Check-in is at 4:00 pm, but you are welcome to drop your bags early to start exploring the ‘Holy City’!
- Head to the Signers Ballroom at 4:30 pm to grab some refreshing iced tea, lemonade, and hors d’oeuvres while you mingle with other guests before heading out to dinner.
- Enjoy a dinner at The Darling Oyster Bar.This vintage raw oyster bar celebrates the bounty of the sea and the joy of shared moments.
- Make your way over for a nightcap at The Gin Joint, one of Charleston’s original craft cocktail bars and a favorite among locals and visitors alike. This intimate, dimly lit gem is known for its expertly crafted drinks, creative flavor pairings, and a rotating menu that reflects the best of the city’s beverage scene.
- Head back to John Rutledge House Inn® for a delicious glass of port, brandy, or sherry before retiring to your beautifully appointed room.
Friday
- Start the first full day of your Girls Getaway with a breath of fresh air as you enjoy your deluxe cooked Continental Breakfast in our lush courtyard.
- Step outside and hop on the shuttle to Middleton Place for a Pineapple Tour through 65 acres of America’s oldest landscaped gardens, historic homes, working stableyards, and powerful stories of the people who shaped this National Historic Landmark.
- After a deliciously authentic lunch, rest your legs and enjoy a horse-drawn carriage ride through the historic streets of South of Broad.
- Walk the Charleston City Market, chatting with local vendors and browsing handmade goods. If you’re feeling peckish, grab an assortment of fresh biscuits from Callie’s Hot Little Biscuit for a taste of the South.
- Head back to get ready in your historic room because it’s time for dinner and a show! Head over to The Establishment for delicious seafood and live music.
- Head back just in time for turndown service. Tuck yourself into bed knowing you have another day of your Girls Getaway ahead!
Saturday
- To start off Day 3, head to brunch at Millers All Day. From hearty Southern breakfasts to perfectly crafted morning cocktails, you’ll have just the boost you need to start your day in Charleston style.
- Stroll down King Street to the Battery for historic mansions and harbor views, then snap the perfect Instagrammable shot at Rainbow Row’s colorful homes. Finish at Waterfront Park with a must-have pic by the iconic Pineapple Fountain.
- Rest and refresh with a nibble at Bin 152, a wine and cheese bar just away from the action on King Street.
- Head down to Candlefish to create a unique souvenir and bring home the scent of Charleston!
- Return to John Rutledge House Inn® and unwind before dinner with light bites and chilled tea in the Signers Ballroom at 4:30 pm.
- Hop on a Charleston Rickshaw to and from an early dinner at Circa 1886, our sister restaurant, tucked within the original carriage house of Wentworth Mansion®.
- Set sail on a sunset cruise aboard the Schooner Pride. This two-hour sail offers the ultimate girls’ getaway moment—relax on deck, sip a drink, and take in Charleston’s skyline as the sun sets over the harbor.
Sunday
- Watch the sun rise and start your final day with a delicious complimentary deluxe cooked Continental breakfast in bed.
- Spend the morning strolling King Street and enjoying a bit of refined retail therapy. From local boutiques and antique shops to art galleries, there’s something to delight every taste. If you’re catching a flight home, be sure to keep airline luggage limits in mind as you shop.
- Check out by noon but leave your bags if you don’t need to rush to the airport and continue to explore Charleston!
More Tips!
- Head off of the peninsula to any of our neighboring beaches and relax away! Check out our Beach Guide and get your toes in the sand.
- Live Music! Check for live music performances at local venues like the Charleston Music Hall and Henry’s On The Market.
- In a city known for its craft cocktails, why just sip when you can shake your own? Gather your girls and join Shaking with the Seasons for a hands-on, flavor-packed cocktail class you won’t forget.
To help ensure you capture the full Charleston experience, we highly recommend booking your dinner reservations and other attractions in advance. Please call 843-723-7999 if you would like our concierge team to assist you in any way.
Please note: All details in this itinerary are accurate at the time of publishing. However, events, schedules, and availability are subject to change without notice. We recommend confirming with venues or organizers for the latest updates before making travel arrangements.