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Experience the stories that shaped a nation.
Winter Escape to Charleston
7-Day Itinerary
Available Year Round - Starting from $5,879 per guest
Experience the rhythm of Charleston on a seven-day getaway full of flavor, charm, and stories waiting to be discovered. Stroll through cobblestone streets, shop local markets, and dig into the city’s food scene with private tastings and fun cocktail experiences. Explore historic homes, peaceful plantations, and coastal corners that feel like a step back in time. After dark, dive into ghost stories and candlelit adventures that show you a whole new side of the city. Whether you’re savoring fresh seafood, walking through centuries of history, or just soaking up the Southern hospitality, this trip delivers all the good stuff without ever feeling rushed.
What We Love About This Experience
“The mix of hands-on food experiences and just enough free time makes this feel like a true vacation. It’s fun, easy, and still packed with meaningful moments.”
Cecilia Krolik
FIT Experience Designer
“This itinerary gives travelers a little bit of everything – good food, beautiful places, and time to breathe. It’s the kind of trip people talk about long after they’re home.”
Christina Ortiz
FIT Experience Designer
“Guests love that this trip doesn’t feel rushed. It’s relaxed, full of flavor, and lets them really soak up Charleston at their own pace.”
Ronnetta Stanley
FIT Experience Designer
Embark On An Unmatched Journey Of A Lifetime
Our expert team has put together a sample itinerary designed to inspire your next vacation – and we’re all about customizing it to match your interests, budget and schedule for a genuine local experience. Looking to add a tour, include additional transportation, extend your hotel stay or include a unique touch? Our Experience Designers are here to make it all happen for you!
This is a suggested itinerary – we can customize based on your preferences.
Day 1 - Your Winter Welcome
- Arrive in Charleston and be greeted by your private driver who whisks you off to the elegant Hotel Bennett or another top-tier hotel that puts you right in the heart of the city’s charm.
- Settle in for a comforting Southern lunch in a warm, welcoming space, then wander the Charleston City Market for local finds and a little early inspiration.
- Check in, settle in, and enjoy dinner at a relaxed coastal spot where fresh seafood and seasonal dishes take center stage
- End the night your way – maybe a quiet stroll by gaslight or a nightcap with a view.
Day 2 – Fresh from the Farm, Straight to Your Plate
- Begin the day with a private market-to-table experience in one of Charleston’s most charming neighborhoods. Pick fresh ingredients alongside your chef, enjoy a guided stroll through Cannonborough Elliotborough, and sit down to a delicious lunch crafted from your market selections.
- After lunch take the afternoon to relax or explore at your own pace.
- Dinner is served in an inviting space known for polished Southern flavors and timeless charm.
- Take in the glow of the Pineapple Fountain as the city settles into evening.
Day 3 – Garden Paths and Ghost Stories
- Walk the grounds of Middleton Place with a guide who knows the stories behind the stone. The gardens, the river views, the legacy – it’s unforgettable.
- After lunch on-site, head back to town to freshen up before dinner at a classic steakhouse-style spot known for bold flavors and low-key elegance.
- Once the sun sets, join a ghost and graveyard tour that peels back the city’s polished layers and reveals its haunted heart.
Day 4 - Decks, Docks, and Dockside Dining
- Head across the famed Ravel Bridge to Mount Pleasant, to visit Patriots Point, the home of legendary naval history, where you’ll spend your morning exploring historic naval vessels and coastal military history.
- Lunch on your own at one of Mount Pleasant’s casual seafood spots or back in the heart of Charleston.
- Your afternoon is free to shop, relax, or soak up the sunshine.
- Dinner brings you back to the present with a menu that celebrates the South’s evolving flavor story.
Day 5 - Shop, Sip, and Ride in Style
- Start your morning with a Sip ’n Shop tour along King Street, where charming boutiques and local pours make for the perfect blend of style and fun.
- Pause for rooftop views and lunch overlooking the city, before stepping into a horse-drawn carriage for a private ride through Charleston’s historic streets.
- Dinner tonight is in an intimate setting where every small plate is crafted with care and every detail leaves a lasting impression.
- Whether you stay out or turn in, the city’s magic lingers.
Day 6 - Oysters and Ocean Air
- Today you’ll head to Charleston’s Lowcountry for a private oyster farm experience. Learn the craft, meet the makers, and taste the salt-kissed results right from the source.
- Return to Charleston for lunch on your own and enjoy the rest of the afternoon to unwind, shop, or simply take in the city.
- Your final dinner is in a refined, romantic setting where Southern flavors are served with timeless style.
- Cap it all off with one last moonlit stroll through the French Quarter.
Day 7 - Farewell for Now
- Your private driver will meet you at your hotel for a smooth ride to the airport.
- Charleston may be behind you, but the warmth of your winter escape will stay with you long after you’re home.
Hotel Bennett
Nestled in the heart of historic downtown Charleston, Hotel Bennett combines deep-rooted tradition with European-inspired architecture and Southern charm. Steps from the vibrant King Street, it offers a gateway to the city’s culture and class. Guests enjoy luxurious rooms, exceptional dining, and a rooftop with stunning views. Start mornings with coffee and pastries on the terrace, unwind at the urban spa and end the day with a rooftop sunset aperitif.
Amenities
- Restaurant
- Fitness Center
- Bar
- Concierge
- Rooftop Pool
- Spa
The Spectator Hotel
$$$$$
A unique blend of exclusive adventures and tailored experiences – The Spectator Hotel captures the essence of luxury and personalized service from the moment you arrive. Situated where the City Market meets the historic French Quarter, this boutique hotel stands out with its sophisticated charm. It blends the warm grace of Southern hospitality with the vibrant flair of the Jazz Age, offering a truly unique and inviting atmosphere.
Amenities
- Butler Service
- Fitness Center
- Valet Parking
- In-Room Breakfast
- Wi-Fi
- Bar
The Lindy Renaissance Charleston Hotel
$$$$
Discover boutique luxury at The Lindy Renaissance Charleston Hotel, nestled in downtown Charleston’s vibrant heart. With eclectic design and genuine Southern hospitality, guests will enjoy comfort and style. Features include a saltwater pool, a fitness center and rooms decorated with local art and plush bedding. Ideal for business or leisure, this hotel offers a prime location to explore Charleston’s historic charm.
Amenities
- Restaurant
- Fitness Center
- Valet Parking
- Rooftop Pool
- Wi-Fi
- Bar
Inclusions
- Roundtrip Airport Transfers via luxury vehicle including driver gratuity and inside meet & greet upon arrival
- Private Charleston Farm-to-Table Kitchen Experience
- Charleston Semi-Private Middleton Place Tour
- Private Charleston Ghost & Graveyard Tour
- Visit to Patriots Point Naval & Maritime Museum
- Private Charleston Sip ‘n Shop Tour
- Private Daytime Carriage Tour of Charleston
- Private Oyster Farm Tour
- Restaurant Reservation Concierge Service
*Gratuities for the tour guides are not included.
*Cost of meals not included.
*Hotel accommodations available for an additional charge.
More Information
- This experience is offered year-round, seven (7) days a week.
- You can customize the starting location of the tours to fit your schedule.
- All stops, timing and inclusions of the tours are dependent on traffic and weather conditions.
- Want to see something specific? We love to personalize our tours to suit your specific interests and passions!
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Quote from Our Travelers
“Our trip to Charleston with American Stories Travel was awesome! They handled all the details, so we could just kick back and enjoy everything the city has to offer. They made our vacation a custom-made adventure – which we loved because we didn’t waste time doing things we weren’t interested in. We honestly couldn’t have asked for a better experience!”
2024 - H.R.
“Our family had an incredible time exploring the plantations around Charleston with American Stories Travel. The tours were both educational and captivating, really bringing the history to life for us and the kids. It was the highlight of our trip, and we appreciated how everything was so well-organized and family-friendly.”
2024 - J.E.
“My bachelorette weekend in Charleston with American Stories Travel was a hit! Loved the Sip and Shop tour, where we explored local shops with drinks in hand—it was a blast and so unique. The sunset harbor cruise was the perfect way to relax afterward. They nailed it with the planning, making my celebration truly special and seamless!”
2024 - K.C.
“Our family had an incredible time exploring the plantations around Charleston with American Stories Travel. The tours were both educational and captivating, really bringing the history to life for us and the kids. It was the highlight of our trip, and we appreciated how everything was so well-organized and family-friendly.”
2024 - M.K.
“Our Charleston foodie adventure was unforgettable! One of our favorite experiences was when we got to pick out fresh ingredients at a local market and then later returned to a chef-prepared meal with the ingredients we chose! We also did a creative cocktail tour that was super fun. Next stop is Savannah – with American Stories Travel of course!”
2024 - P.G.
