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Winter Escape to Savannah 5-Day Itinerary

Winter Escape to Savannah
5-Day Itinerary

Available Year Round - Starting from $3,426 per guest

Uncover Savannah’s soulful side on this five-day winter escape filled with history, flavor, and Southern charm. Wander storied streets on guided walking tours, dive into local history at top museums, and enjoy a private tour of one of the city’s premier art collections. Savor Savannah’s signature cuisine on a curated food tour, learn to shake up your own craft cocktails, and explore the haunting beauty of Bonaventure Cemetery. Cap it all off with a scenic dinner cruise featuring live entertainment. Each evening includes handpicked dining spots that bring together culture, cuisine, and that unmistakable Savannah warmth.

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 - A Warm Southern Welcome

  • Arrive in Savannah and meet your private driver for a smooth ride to your boutique hotel, like The Perry Lane, or another luxury property that captures the spirit of the city
  • Kick things off with a casual lunch that sets a relaxed and welcoming tone for your stay
  • Spend the afternoon settling in or strolling the Riverfront for a first taste of Savannah’s charm.
  • Dinner is reserved at a local favorite that’s fresh, flavorful, and full of local character.
  • End your day with a peaceful walk under the glow of the city’s historic gas lamps.

Day 2 – Art, Squares, and Rooftop Sips

  • Dive into Savannah’s creative side with a guided visit to the Telfair Museum Trio, from classic to contemporary.
  • Refuel with lunch in a relaxed setting that serves up feel-good flavors and easygoing vibes.
  • Then, hit the streets with a private walking tour through Savannah’s story-filled squares and iconic landmarks.
  • Dinner is at a comfortable spot where good food and a great setting come together.
  • Cap off the evening with a drink and a view – an easy way to soak in the city at night

Day 3 – Bold Bites and Craft Cocktails

  • Explore the SCAD Museum of Art with a private guide and see where innovation meets artistry.
  • Get a real taste of the city on the Port City Food Tour—expect bold flavors, hidden gems, and stories in every bite.
  • After lunch on tour, take some time to relax or explore on your own.
  • Dinner is at a stylish, chef-inspired spot where bold flavors and a lively atmosphere make for a fun night out.
  • Tonight’s highlight: a private cocktail class at the American Prohibition Museum, where you’ll shake, stir, and sip your way into Savannah’s spirited past.

Day 4 - Haunting Beauty and River Views

  • Begin the day with a private tour of Bonaventure Cemetery. It’s peaceful, poetic, and unlike anywhere else.
  • Take a midday break at a relaxed bistro-style spot that blends casual comfort with just a hint of elegance.
  • The afternoon is yours—shop, wander, or simply take it all in.
  • In the evening, step aboard a Savannah River Dinner Cruise. Enjoy live entertainment, local flavors, and golden hour views as the city floats by.

Day 5 - Sweet Sendoff

  • Your private driver picks you up for a smooth ride to the airport.
  • One last look at the oak-lined streets and you’ll already be planning your return.

JW Marriott Savannah Plant Riverside District

Rating
Rated 5 out of 5
Pricing: $$$$$

At the heart of Savannah’s riverfront, the JW Marriott Savannah Plant Riverside District blends history with luxury. Steps away from lively shops and eateries, it’s a prime spot for exploring or unwinding. From its power plant past to the eclectic chic of its buildings, it’s a place where stories come alive. Treat yourself to a spa day, then dive into the city’s vibrant nightlife—all in one unforgettable setting.

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

The Bohemian Hotel Savannah Riverfront, Autograph Collection

Rating
Rated 4 out of 5
Pricing:
$$$$

In the heart of Savannah, where historic cobblestones meet the river, The Bohemian Hotel offers a unique escape. Steps from iconic sites, this boutique hotel blends colonial elegance with modern comforts. Enjoy breathtaking views, Southern hospitality and gourmet delights at their restaurant and rooftop bar. It’s your perfect base to experience the charm and vibrancy of Savannah’s Historic District.

Amenities

Inclusions

  • Roundtrip Airport Transfers via luxury vehicle including driver gratuity and inside meet & greet upon arrival
  • Private Tour Of Three Telfair Museums: Telfair Academy, Jepson Center, and Owens-Thomas House & Slave Quarters
  • Private Historic Savannah Walking Tour
  • Private Guided Tour of SCAD Museum of Art
  • Private Savannah Port City Food Tour
  • Private Speakeasy Cocktail Experience in Savannah
  • Savannah Private Half-Day Bonaventure Cemetery Tour
  • Dinner Entertainment Cruise
  • 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!

Enrich Your Experience with
Captivating Enhancements

Like this itinerary? Request a Quote!

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Quote from Our Travelers

“We saw so much – things that we didn’t even know we wanted to see! And everything was personalized tour our interests – which made it 100 times better! So many great experiences but the highlight was our private tour with our expert local guide! It felt like exploring Savannah with an old friend. We absolutely recommend American Stories Travel for a personal touch on your trip!”

2024 - G.K.

“Traveling to Savannah with American Stories Travel was a great choice! They took care of all the details, from the ghost tours to the best spots for Southern eats. I’d recommend them to anyone who wants a hassle-free, fun trip. They know their stuff and make it all about what you enjoy!”

2024 - J.M.

“My girlfriends and I decided to do a girl’s weekend in Savannah trip and wanted it to be super special. We had no idea what we wanted to do. Our Experience Designer came up with an itinerary that had something for each of us – from a riverboat cruise to the beautiful but spooky Bonaventure Cemetery to a private pedicab ride and more. I can’t recommend them enough!”

2024 - L.D.

“We celebrated our anniversary in Savannah and thanks to American Stories Travel it was an amazing time! We are both foodies and did a lot of food-centered experiences – a food tour through the historic squares, a luncheon harbor cruise and our absolute favorite – a Lowcountry cooking class! We’ve already decided to use them for our next anniversary which will be in Charleston.

2024 - P.R

“Our family trip to Savannah with American Stories Travel was fantastic! The kids loved the riverboat cruise, and we all enjoyed learning about the history of Bonaventure Cemetery. They made sure there was something for everyone, which made our trip stress-free and super memorable.”

2024 - R.G.

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