Timeless Days in Charleston & Savannah 7-Day Itinerary

Available Year Round - Starting from $6,936 per guest

Discover the soul of the Lowcountry on a seven-day journey through Charleston and Savannah. Wander cobblestone streets and pastel-lined avenues, explore scenic plantations steeped in history, and savor the South’s rich culinary heritage one bite at a time. In Charleston, explore tea fields, hidden gardens, and grand homes, then feel the city shift after dark with ghost stories and candlelit charm. In Savannah, drift beneath moss-draped oaks, wander Bonaventure Cemetery, stroll elegant squares, and indulge in a curated food adventure rich in flavor and Southern warmth. It’s a week of living history, artistic beauty, and that signature hospitality only found in the South.

What We Love About This Experience

“Charleston and Savannah are two cities that speak to the senses. Every meal, every street, every tour has a story behind it – and this itinerary brings those stories to life.”

Jenine Bett

FIT Experience Designer

“I love that this itinerary has a little bit of everything. One minute you’re relaxing in a quiet garden, the next you’re listening to ghost stories under the stars.”

Mary Eggert

FIT Experience Designer

“This trip gives travelers a chance to slow down and connect with the history, the food, and the feeling of the South. It’s unforgettable in the best way.”

Cecilia Krolik

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 - Southern Arrival, Southern Charm

Step off the plane and into a private luxury vehicle, where your driver greets you with a smile and a welcome to Charleston.
Check into The Spectator or another top-tier hotel that puts you right in the heart of the city’s charm.
Head to a trendy place near City Market for a light lunch and a dose of local flavor.
Enjoy a reservation at one of Charleston’s fine dining spots for dinner, where Lowcountry classics get a refined twist.
End your first night with a sunset walk to the Pineapple Fountain. It’s the perfect first chapter.

Day 2 – Taste the City, Feel the Spirit

Begin with a guided culinary tour through Downtown or Upper King Street. You’ll taste your way through Charleston’s heritage with every bite.
After lunch, hop into a horse-drawn carriage and ride past steepled churches and pastel homes.
For dinner, take your seat at a beloved Lowcountry spot where Southern flavors meet creative flair and every dish tells a story
Cap the evening with a ghost and graveyard tour that brings Charleston’s legends to life.

Day 3 – Gardens, Grandeur, and Quiet Moments

Spend the day at Middleton Place, a former rice plantation with America’s oldest landscaped gardens and a powerful story to tell. Your semi-private tour leads you through centuries-old gardens and stories of the past.
Enjoy lunch on-site with views that stretch across the Ashley River.
Back in Charleston, dine at a refined local favorite that pairs Southern charm with warm hospitality
After dinner, take a peaceful walk through the French Quarter as the city slows down for the night.

Day 4 - From Tea to Spanish Moss

It’s time to say goodbye to Charleston as you head south toward Savannah.
Your first stop on the way out? The Charleston Tea Garden, where you’ll explore the only tea plantation of its kind in North America.
Stop for a relaxed lunch along the way, then continue your journey south to Savannah.
Check into The Perry Lane Hotel or another luxury property that captures the spirit of the city.
That evening, enjoy dinner at a cozy, chef-loved spot that blends creativity with comfort.
After your meal, stroll the Riverwalk’s cobblestone streets and enjoy the water views.

Day 5 - Legends, Squares, and Stories

Tour Bonaventure Cemetery with a private guide. Every path winds through beauty, memory, and mystery.
Lunch is served at a local favorite that blends familiar flavors with warm Southern hospitality.
Walk Savannah’s Historic District and feel the city unfold around every square.
Dinner is reserved at a welcoming spot that captures the charm of the city. End the night your way, whether it’s a jazz bar or a quiet porch swing.

Day 6 - Art Meets Appetite

Spend your morning inside the Telfair Museums on a private tour that brings Savannah’s creative soul to life.
Take a First Squares Food Tour for a delicious, immersive experience that blends history with every bite.
Celebrate your final night with dinner at a stylish spot where the atmosphere is memorable and the flavors leave a lasting impression.
Toast to an incredible week and soak in your last Savannah evening.

Day 7 - Farewell, For Now

Your private transfer picks you up at your hotel. As you make your way to the airport, reflect on the stories, flavors, and people that made this week unforgettable.
The journey may be ending, but the memories are just beginning.

The Spectator Hotel

Rating

Rated 5 out of 5

Pricing: $$$$$

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

Perry Lane Hotel, a Luxury Collection Hotel, Savannah

Rating

Rated 5 out of 5

Pricing:
$$$$$

Nestled among Spanish moss-draped oaks, Perry Lane Hotel is a blend of Southern grace and contemporary luxury in Savannah. Hop on a bike to explore the cobblestones and historic sights, from Forsyth Park to Chippewa Square. Inside, find a mix of local art, boutique comfort and a vibe that invites both relaxation and adventure. It’s the perfect spot for soaking up Savannah’s charm and excitement, with every detail crafted to enhance your journey.

Amenities

Inclusions

Roundtrip Airport Transfers via luxury vehicle including driver gratuity and inside meet & greet upon arrival
Charleston Culinary Tour – Downtown or Upper King Street
Private Horse & Carriage Tour of Charleston
Private Charleston Ghost & Graveyard Tour
Charleston Semi-Private Middleton Place Tour
Transportation between Charleston and Savannah
Charleston Tea Garden Trolley Tour
Savannah Private Partial Day Bonaventure Cemetery Tour
Private Historic Savannah Walking Tour
Private Tour of the Three Telfair Museums: Telfair Academy, Jepson Center, and Owens-Thomas House & Slave Quarters
Private Savannah First Squares Food 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.

*Hotels listed are suggestions and can be substituted.

*Itinerary can be reversed to start in Savannah and end in Charleston.

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!

Enrich Your Experience with
Captivating Enhancements

Private Savannah Drums & Shadows South Carolina Tour