★ What's included in Now Journey's Limited Series' Tour:
- Lead by our very own Tour Captain beginning to end.
- Limited Small Group up to 8 Guests: Enjoy a more personal and immersive way to explore.
- Privately Guided Historical Tours with expert local English-speaking guides.
- Signature Discovery Walks in each destination.
- Now Journey Exclusives throughout
- Arrival Transfer: Included Meet & Greet upon arrival.
- Scenic Coastal & Southern Travel
- Luggage Portaged: Handling through your Journey. No surprise up-sells.
- Comfortable Scenic Travel with premium vehicles, thoughtfully paced routing, and beautiful drives. No large buses.
- Deluxe Hand-Picked Hotel Properties selected for character, location and service.
- Transparent Pricing: No hidden fees or taxes. Gratuities included, except for the Tour Captain.
- City Taxes Included — no surprise hotel charges.
- Distinctive Southern Dining with Premium Included Beverages.
★ Itinerary at a Glance:
- TOUR BEGINS: ST. AUGUSTINE, 2 Nights
Fly into Jacksonville Airport (JAX) or NE Floreida Regional (UST).
- SAVANNAH, 3 Nights
Romantic. Haunting. Timeless.
- TRIP FINALE: CHARLESTON, 3 Nights
Elegant. Historic. Refined.
Chapter 1: Arrival in St. Augustine
America's Oldest City —
2 Days, 2 Nights
DAY 1: Welcome to St. Augustine
Welcome to St. Augustine — a city where Old World Spain meets the relaxed elegance of Florida’s historic coast. Founded in 1565, St. Augustine feels unlike anywhere else in America. Narrow brick lanes, hidden courtyards, centuries-old architecture, and softly glowing lanterns create an atmosphere that feels almost European in spirit.
Guests settle into the magnificent Casa Monica Resort & Spa — a landmark luxury property blending Moorish Revival architecture, rich textures, dramatic archways, and timeless Southern elegance in the very heart of the Historic District.
Discovery Walk
This evening, step beyond the grand doors of the Casa Monica Resort & Spa and into the softly glowing streets of America’s oldest city. Your Tour Captain leads a relaxed introductory walk through centuries-old lanes, hidden courtyards, Spanish colonial architecture, and lantern-lit corners where history still feels wonderfully alive. Along the way, discover the atmosphere, stories, and rhythm of St. Augustine before gathering for your Welcome Dinner in the heart of the historic district.
Welcome Dinner — Southern Delights
Tonight’s cuisine introduces the flavors of Florida’s historic coast — blending Spanish influence, fresh Atlantic seafood, citrus-forward specialties, handcrafted cocktails, and warm coastal hospitality in a beautifully atmospheric setting.
Where We Stay in St. Augustine, 2 Nights with breakfast
Deluxe Hotels Collection —
Casa Monica Resort & Spa or Similar
The Casa Monica Resort & Spa is a landmark Moorish Revival hotel in the heart of historic St. Augustine, celebrated for its romantic architecture, rich Old World atmosphere, and refined coastal elegance.
DAY 2: ST. AUGUSTINE & THE GILDED COAST
Today's Adventure: Forts & Secrets
This morning, we explore the layered story of St. Augustine alongside our local storyteller-guide as centuries of Spanish colonial history, coastal beauty, and Gilded Age elegance unfold throughout the city.
Highlights include:
• Castillo de San Marcos
• Flagler-era architecture
• Cathedral Basilica
• Aviles Street
• Lightner Museum
• Historic plazas & hidden courtyards
The afternoon is intentionally left open for guests to enjoy the city at their own pace. Perhaps enjoy rooftop cocktails overlooking the bay, browse independent boutiques and galleries, or relax within the timeless atmosphere of the Historic District.
Tonight, join the Tour Captain for an optional dinner or enjoy exploring at your leisure.
BACK TO TOP Got a question? CHAT HERE.
Chapter 2: To Savannah
The Romantic South —
3 Days, 3 Nights
DAY 3: SAVANNAH, GEORGIA
Today's Adventure: Oak & Moss — Making our way to Savannah
Today we make our way north along the Atlantic coastline toward the timeless beauty of Savannah — a city where towering oak trees draped in Spanish moss frame elegant historic squares, hidden gardens, wrought-iron balconies, and beautifully preserved Southern mansions.
Savannah carries a slower rhythm — one built around atmosphere, storytelling, hospitality, and lingering moments beneath the trees.
Upon arrival, guests settle into the intimate and historic Hamilton Turner Inn, beautifully positioned directly on Lafayette Square in the heart of Savannah’s Historic District.
Discovery Walk
Our property is surrounded by moss-draped oaks, elegant mansions, and the quiet rhythm of one of the South’s most iconic neighborhoods, the inn offers a warm and refined introduction to Savannah’s timeless character as we explore our new home for the next 3 days and nights.
Welcome Dinner — The Southern Dinner
Tonight, we gather for a special Welcome Reception and Dinner — an evening shaped by conversation, Southern hospitality.
Savannah’s cuisine reflects generations of Southern hospitality and Lowcountry tradition — featuring regional seafood, shrimp & grits, slow-prepared Southern specialties, bourbon-forward cocktails, and warm candlelit ambiance that perfectly complements the city’s romantic atmosphere.
Where We Stay in Savannah, 3 Nights with breakfast
Deluxe Hotels Collection —
Perry Lane Hotel or Similar.
Located in the heart of the historic district, the Perry Lane Hotel is a stylish, top-rated Luxury Collection hotel offering sophisticated, art-filled accommodations with a chic rooftop pool and popular dining experiences.
BACK TO TOP Got a question? CHAT HERE.
DAY 4: Exploring Savannah
Today's Adventure: Beauty Beneath the Oaks
Savannah reveals itself slowly — through quiet garden squares, elegant mansions, hidden alleyways, and stories woven deeply into the city’s Southern character.
Today’s guided exploration uncovers both the beauty and fascinating history that make Savannah one of America’s most atmospheric destinations.
Today’s guided exploration reveals the timeless beauty and layered history of Savannah through its elegant squares, hidden residential lanes, and atmospheric gardens. Highlights include iconic Forsyth Park, the historic waterfront along River Street, the stunning Cathedral Basilica of St. John the Baptist, Colonial Park Cemetery, and the famed Mercer-Williams House area — all woven together through the city’s uniquely graceful Southern character.
Today's Adventure includes:
- Forsyth Park
- Historic Squares
- River Street
- Cathedral Basilica of St. John the Baptist
- Colonial Park Cemetery
- Mercer-Williams House area
- Hidden residential lanes & gardens
This afternoon allows time for personal exploration, relaxed cafés, rooftop lounges, boutiques, or optional local experiences throughout the city.
Tonight, join the Tour Captain for optional dinner or enjoy exploring at your leisure.
BACK TO TOP Got a question? CHAT HERE.
DAY 5: SAVANNAH AT LEISURE
Today is intentionally slower.
Sleep in. Wander slowly. Linger a little longer.
Savannah rewards those who slow down enough to notice its details — the sound of fountains beneath the oaks, quiet church bells echoing through the squares, and the rhythm of life along its historic streets.
Guests may choose to:
- enjoy brunch beneath the trees
- visit Bonaventure Cemetery
- explore local boutiques and galleries
- take a Tybee Island coastal excursion
- simply relax and savor the atmosphere
Tonight join the Tour Captain for an optional dinner or explore at your leisure.
Chapter 3: To Charleston
Beauty Beneath the Oaks —
3 Days, 3 Nights
DAY 6: Welcome to Charleston
Making our way to the Sea
Today we continue northward into the refined elegance of Charleston — one of America’s most celebrated and atmospheric coastal cities. Charleston blends historic grandeur, harbor beauty, pastel-colored architecture, hidden gardens, and sophisticated Southern charm into a city that feels both timeless and effortlessly elegant.
Upon arrival, guests settle into the luxurious Hotel Bennett overlooking historic Marion Square in the very heart of downtown Charleston.
Discovery Walk
As evening settles over the city, we enjoy a relaxed Discovery Walk before gathering for a beautifully curated Charleston Welcome Dinner celebrating the refined flavors of the Lowcountry.
Welcome Dinner — Coastal Traditions
We enjoy an amazing dinner tonight in Charleston hosted by your Tour Captain. Charleston’s culinary scene elevates Southern coastal traditions into something refined, elegant, and unmistakably local — featuring fresh regional seafood, Lowcountry specialties, artisan cocktails, thoughtful wine selections, and beautifully curated dining settings.
Where We Stay in Charleston, 3 Nights with breakfast
Deluxe Hotels Collection —
The Charleston Place or Similar.
The Charleston Place is Charleston’s grand luxury landmark — an elegant and beautifully appointed hotel in the heart of the Historic District known for its refined Southern hospitality, sophisticated atmosphere, and exceptional walkable location.
Charleston blends refined beauty, coastal elegance, and deeply layered American history into one unforgettable experience best enjoyed at a slower rhythm.
Today’s exploration reveals the city’s iconic landmarks, hidden corners, waterfront atmosphere, and celebrated harborfront.
Today's Highlighs Include:
- Rainbow Row
- The Battery
- Waterfront Park
- Historic Charleston Market
- Hidden Alleys & Gardens
- Historic Mansions and Church District
The afternoon and evening are open for guests to enjoy Charleston at their own pace — from harborfront cocktails and rooftop lounges to boutique shopping and exceptional Lowcountry dining.
Tonight join the Tour Captain for an optional dinner or explore at your leisure.
BACK TO TOP Got a question? CHAT HERE.
DAY 8: Charleston at Leisure
Our final full day invites you to experience Charleston at your own pace — perhaps exploring the beauty of Magnolia Plantation & Gardens, browsing the boutiques and galleries along King Street, relaxing at a harborfront café, or simply slowing down to savor the final moments of the journey before returning home.
Later tonight, we enjoy a magical Finalé to our adventure.
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Our Special Journey Farewell Dinner
As evening settles across Charleston, we gather one final time for a special Farewell Reception and Dinner celebrating the stories, laughter, friendships, and unforgettable moments shared throughout the South.
DAY 9: Departure Day
After breakfast, private departure transfers are available to the airport - inquire.
And somewhere between the lantern-lit streets of St. Augustine, the shaded squares of Savannah, and the harbor breezes of Charleston…you may realize this journey wasn’t simply about seeing the South.
It was about slowing down long enough to let its stories, beauty, and spirit stay with you long after the journey ends.
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