Charleston History Multiday Experience

Available Year Round - Starting from $2,462 per guest

Charleston is steeped in history and this enchanting experience is the perfect way to take it all in. You’ll enjoy an iconic horse and carriage ride, delve into the riveting tales of the city with an expert local guide and feel the hair on the back of your neck stand up during a graveyard adventure. You’ll also explore architectural wonders, unwind with a sunset cruise, delight your inner foodie and more! The best part? All this can be personalized to your interests!

What We Love About This Experience

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 Ride Awaits

Your luxury experience starts when you’re met inside the airport with a smile by your friendly driver – who’ll be holding a sign with your name on it. After settling in, why not introduce yourself to Charleston’s culinary scene by having lunch or dinner in one of the city’s renowned restaurants? 

Day 2 – Horses, History & Haunts

  • Your day starts at the Big Red Barn where you’ll greet your carriage driver and the horses that will whisk you away on a private tour through Charleston’s historic streets.
  • After a stop for lunch, you’ll join an expert guide for the Charleston Saga walking tour where you’ll hear all the captivating tales of society, scoundrels and conflicts that shaped the city.
  • You’ll enjoy dinner on your own – and then after dark – it’s a time for some spooky fun courtesy of a ghost and graveyard private experience.

Day 3 - From Cobblestones To Cruising

  • Today starts when you hop into a private vehicle with an expert guide for a captivating tour of Charleston’s stunning architecture, historic cobblestoned streets and most iconic landmarks. 
  • You’ll enjoy lunch on your own then continue the adventure on foot, exploring the poignant history of the Civil War and slavery on a private walking tour.
  • Later that evening you’ll bask in the sunset during a harbor cruise where you’ll take in Charleston’s charm from a dazzling new perspective.

Day 4 –Stable Yards, Strolling & Savoring

  • Today starts with a luxury ride to Middleton Place where you’ll explore America’s oldest landscaped gardens and enjoy a delicious Lowcountry lunch.
  • The afternoon is yours to check out the city’s stunning sites and perhaps partake in some retail therapy.
  • Your day ends with a private culinary tour of either Downtown Charleston or Upper King Street, where you’ll taste incredible dishes from some of the city’s top restaurants.

Until We Meet Again

When your unforgettable experience in Charleston comes to an end, you’ll be met at your hotel by your driver for your private transfer back to the airport via luxury vehicle.

Hotel Bennett

Pricing: $$$$$

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. 


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. 


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. 



  • Roundtrip Airport Transfers via luxury vehicle including driver gratuity and inside meet & greet upon arrival
  • One (1) Hour Private Horse & Carriage Ride
  • Two to Three (2 to 3) Hour Private Charleston Saga Walking Tour
  • One and a Half (1.5) Hour Private Ghost & Graveyard Walking Tour 
  • One and a Half (1.5) Hour Private Historic Driving Tour of Charleston 
  • One and a Half (1.5) Hour Private Charleston Civil War & Slavery Walking Tour
  • One and a Half (1.5) Hour Sunset Harbor Cruise aboard the Carolina Belle 
  • Two and a Half (2.5) Hour Private Downtown or Upper King Street Culinary Tour 
  • Half Day Tour of Middleton Place & Private House Tour with Lunch

*Gratuities for the tour guides are not included.

*Cost of meals not included unless noted.

*Hotel accommodations available for an additional charge.

More Information

  • This experience is offered year-round, seven (7) days a week except Christmas Day and New Year’s Eve.
  • 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!

Enrich Your Experience with
Captivating Enhancements

Quote from Our Travelers

“Our trip to Charleston with Beyond Times Square 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 Beyond Times Square. 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 Beyond Times Square 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 Beyond Times Square. 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 Beyond Times Square of course!”

2024 - P.G.