SEE ITINERARY | DATES & PRICES | FAQs | MAKE A RESERVATION★ What's included in Now Journey's Italy's Hidden Chapters Tour:
- Friendly, entertaining Tour Captain beginning to end.
- True Small Group: Enjoy a more personal, immersive experience.
- Privately Guided Tours: Local easy-to-understand, English-speaking Guides.
- Signature Discovery Walks in each city.
- Arrival Transfer: Included Meet & Greet from Venice Marco Polo Airport (VCE).
- Luggage Portaged: Handling through your Journey. No surprise up-sells.
- Comfort All the Way: Premium Fast Train and Micro-concept luxe vans. No buses.
- Hand-Picked Hotels and Villas: 4+ to 5-star properties.
- Transparent Pricing: No hidden fees or taxes. Gratuities included, except for the Tour Captain.
- City Taxes Included — no surprise hotel charges.
- UNIQUE IN THE INDUSTRY DINING with Unlimited Premium Beverages.
★ Itinerary at a Glance:
- TOUR BEGINS: THE VENETO, 3 Nights
Fly into Venice or Bologna airports.
- UMBRIA:Villa located near Narni in Ubmria, 3 Nights
- TRIP FINALE: CALABRIA: Tropea, 3 Nights
Chapter 1: The Veneto
Where Villas, Vineyards & Time Slow Down —
3 Days, 3 Nights
DAY 1: BENVENUTI IN VENETO
Your Journey begins not in a crowded city, but in the rolling countryside of northern Italy — where vineyards stretch toward the horizon and historic villas quietly hold centuries of stories.
After arrival in Venice or Verona, meet your Now Journey Tour Captain and transfer into the heart of the Veneto countryside to our elegant villa estate (yes, you can come in early and stay in Venice — Why Not? — Just inquire with us).
Take time to settle in at the Villa estate, breathe deeply, and let Italy greet you properly.
Welcome to the Veneto
Beyond the famed cities, the Veneto countryside unfolds as a tapestry of Palladian villas, vineyard-lined roads, and gentle plains framed by distant mountains. Life here moves with a refined rhythm — shaped by centuries of agriculture, artistry, and noble estates — where wine, architecture, and landscape coexist in quiet harmony. It’s a region that reveals Italy’s grace not through spectacle, but through balance, beauty, and tradition lived daily.
Discovery Walk
Your Tour Captain introduces the estate, its grounds, and the surrounding countryside — the perfect gentle welcome to this slower, more intimate Italy.
Welcome to Veneto Dinner — A Villa Evening
Tonight, we gather for our first Now Journey welcome dinner — a beautifully prepared regional meal served at the villa, paired with Veneto wines and premium beverages. Conversation flows easily as strangers begin to feel like friends.
Where We Stay in the Veneto, 3 Nights with breakfast
Now Journey Hotels Collection —
Historic Veneto Countryside Villa or Similar Elegant rooms, pastoral views, and an atmosphere that invites you to linger.
Enjoy hand-selected 4-Star and 5-Star hotels and villas.
DAY 2: Life Among the Vines
Today's Adventure: Veneto Secrets & Flavors
Today unfolds at an easy, intentional pace — a day devoted to the quiet pleasures of the Veneto countryside, where tradition, flavor, and landscape come together naturally.
Our journey takes us into the heart of the Valpolicella wine region, a land of rolling vineyards, stone estates, and generations of winemaking history. Enjoy a private cellar visit and guided tasting, offering insight into the wines that have defined this region for centuries.
From there, we linger over a countryside lunch, featuring fresh, seasonal ingredients and regional specialties — simple, honest food meant to be savored, not rushed.
Special sightseeing today includes:
• Valpolicella Wine Region: Rolling vineyards and story-rich estates
• Winery Experience: Private cellar tour and tasting
• Countryside Lunch: Farm-to-table regional specialties
• Villa Time: Afternoon leisure to enjoy the estate grounds, gardens, or pool
The afternoon invites you back to the villa for unstructured leisure. Wander the gardens, enjoy the pool, or simply settle into the rhythm of the estate and let the day breathe.
This evening is yours to enjoy at a relaxed pace. A light Italian apericena is provided at the villa — the perfect close to a beautifully balanced day.
BACK TO TOP Got a question? CHAT HERE.
DAY 3: The Veneto at Leisure
Sleep in. Enjoy a long breakfast. Wander the grounds. Read. Write. Reflect. Enjoy a long, unhurried breakfast. Wander the grounds. Read. Write. Reflect. Let the villa — and the Veneto — set the rhythm.
May We Suggest?
• A relaxed cooking demonstration with the villa chef — included at no charge
• A visit to a nearby countryside village for a glimpse of everyday life
• Or simply doing nothing at all — a luxury in itself
As evening approaches, we gather casually to toast our final night in the Veneto — grateful for a slower pace, shared moments, and a beautiful beginning to the journey.
BACK TO TOP Got a question? CHAT HERE.
Chapter 2: Umbria
Italy's Green Heart —
3 Days, 3 Nights
DAY 4: ONWARD TO UMBRIA
After breakfast, we journey south into Umbria — Tuscany’s quieter, more soulful cousin. Vineyards give way to olive groves. Hill towns rise softly from the landscape. The pace shifts once again, inviting you to slow down and take it all in.
Upon arrival, settle into our Umbrian villa estate — secluded, timeless, and wrapped in a sense of calm that feels instantly grounding.
Welcome to Umbria
Often called the green heart of Italy, Umbria offers a deeply rooted sense of authenticity — a land of hill towns, olive groves, and stone villages seemingly untouched by time. Here, ancient traditions endure in family kitchens and village piazzas, where food, faith, and community remain central to daily life. Umbria’s beauty is subtle and soulful, rewarding those who slow down and truly engage with its rhythms.
Today's Adventure: Umbrian Hill Town & Villa Grounds
This afternoon, your Tour Captain offers a gentle introduction to the region — its history, traditions, and quiet beauty — as we explore nearby lanes, scenic viewpoints, and the surrounding villa grounds.
Welcome to Umbria Dinner — Rustic Elegance
Tonight, we gather for a dinner that celebrates Umbrian cuisine at its best: truffles, exceptional olive oil, hand-rolled pastas, and local wines, all enjoyed beneath the warm glow of an Italian evening.
Where We Stay in Umbria, 3 Nights with breakfast
Now Journey Hotels Collection —
Umbrian Countryside Villa or Similar
Panoramic views, quiet mornings, unforgettable sunsets.
DAY 5: UMBRIA’S QUIET MAGIC
Today's Adventure: Umbrian Secrets & Treasures
Today invites you into the quiet soul of Umbria — a land shaped by monks, farmers, and artists, where daily life still follows an unhurried rhythm.
Our exploration includes time in a storybook hill town, wandering medieval lanes and discovering hidden piazzas where centuries of life have unfolded. We continue with a local olive oil or wine estate visit, offering a deeper look at the flavors and traditions that define the region.
A long, leisurely lunch follows — regional specialties enjoyed the Umbrian way: slowly, thoughtfully, and in good company.
Special sightseeing today includes:
• Hill Town Exploration: Medieval streets and hidden piazzas
• Olive Oil or Wine Experience: Estate visit and tasting
• Long Lunch: Regional specialties enjoyed slowly
• Afternoon Leisure: Return to the villa to rest or wander
The afternoon brings us back to the villa for unstructured leisure — time to rest, wander the grounds, or simply enjoy the stillness.
Umbria Dinner — Village Visit
This evening, we head into a nearby village for dinner, with your Tour Captain hosting a relaxed and convivial night centered on local cuisine, conversation, and a sense of place.
DAY 6: A DAY OF CHOICE
Today is intentionally unscheduled — a rare gift of time to follow your own curiosity or simply be still.
May We Suggest?
• A hands-on cooking class at the villa, celebrating Umbrian flavors
• Truffle hunting in the countryside (seasonal)
• A relaxed day trip to Assisi, Spello, or Montefalco
• Or a full day of rest, reflection, and quiet enjoyment of the villa
There is no wrong choice today — only the one that feels right to you.
Farewell to Umbria Dinner — Umbrian Bliss
Tonight, we gather to celebrate our time in Umbria with a beautifully crafted, chef-prepared dinner — a final evening that captures the soul of this region. Using seasonal ingredients and time-honored Umbrian recipes, our chef brings the countryside to the table as we linger over local wines, warm conversation, and the kind of unhurried joy that defines life here. It’s a moment to reflect, connect, and savor Umbria exactly as it’s meant to be experienced.
BACK TO TOP Got a question? CHAT HERE.
Chapter 3: Calabria
The Bluest Waters —
3 Days, 3 Nights
DAY 7: TO THE COAST
Today we transfer to Rome, where we board a short flight south to Calabria. Upon arrival, we continue by private transfer to our hotel in the beautiful coastal city of Tropea.
Perched high above the Tyrrhenian Sea, Tropea is a luminous Calabrian gem of honey-colored cliffs, turquoise waters, and timeless southern Italian charm.
Welcome to Tropea in Calabria
Perched above the Tyrrhenian Sea, Tropea embodies Calabria’s raw beauty and enduring spirit — dramatic cliffs, crystalline waters, and a culture shaped by resilience and pride. This is southern Italy at its most elemental, where bold flavors, sun-washed landscapes, and centuries-old customs create an experience that feels both untamed and deeply welcoming. Calabria doesn’t perform for visitors — it invites them in.
Discovery Walk
After settling in, we’ll step out for our Discovery Walk, getting our first feel for Tropea’s dramatic clifftop setting, winding lanes, and sun-washed views over the Tyrrhenian Sea.
Welcome Dinner — Tropean Splendor
This evening, we gather for a beautiful Welcome Dinner — the perfect way to begin Chapter Three of Italy’s Hidden Chapters, and our time in Calabria. Calabria is bold and soulful — shaped by the sea and sun, celebrated for sweet Tropea red onions, fiery peperoncino, freshly caught seafood, and rustic dishes rooted in centuries-old tradition.
Where We Stay in Calabria, 3 Nights with breakfast
Now Journey Hotels Collection —
Hotel Rocca Della Sena Tropea or Similar
Panoramic coastal views with the bluest of waters.
DAY 8: EXPLORING TROPEA
Today's Adventure: Walking Tour of the Heart
This morning, we set out on a guided walking tour of Tropea, beginning just steps from our hotel. With our local expert leading the way, we explore the historic heart of this dramatic cliffside town — wandering narrow lanes lined with palazzi, hidden chapels, and flower-draped balconies. We pause at scenic viewpoints overlooking the Tyrrhenian Sea and the iconic Church of Santa Maria dell’Isola, learning how Greek, Norman, and Spanish influences shaped Tropea’s story. The walk unfolds at an easy, unhurried pace, allowing time to absorb the beauty, ask questions, and experience Tropea not as visitors, but as guests welcomed into its daily life.
The afternoon will be at your leisure to continue your exploration of this beautiful city on the sea.
Tonight, join the Tour Captain for an optional dinner or explore at your leisure.
DAY 9: LEISURE ON THE COAST
Today is intentionally unscheduled — a rare gift of time to follow your own curiosity or simply be still.
May We Suggest?
• A hands-on cooking class celebrating Calabrian flavors - inquire
• Savor Calabrian Flavors
• Or a full day of rest and reflection
There is no wrong choice today — only the one that feels right to you.
Farewell Dinner
Tonight, we gather to celebrate our time in Tropea with a beautifully crafted, chef-prepared dinner — an evening that captures the sun-kissed soul of Calabria. Drawing from the region’s coastal bounty and time-honored Calabrian recipes, our chef brings sea and land together at the table. As we linger over local wines, fresh flavors, and easy conversation, we settle into the unhurried rhythm of life along Italy’s southern shores. It’s a moment to reflect, connect, and savor Calabria exactly as it’s meant to be experienced.
DAY 10: DEPARTURE DAY: Arrivederci!
Breakfast is included this morning should you have time before your departure. It's about an hour's drive to the airport.