SEE ITINERARY | DATES & PRICES | FAQs | MAKE A RESERVATION★ What's included in Now Journey's Italy's Hidden Chapters Tour:
- Friendly, entertaining Tour Captain from 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 upon arrival in Rome, followed by transfer to Umbria.
- Luggage Portaged: Handling through your Journey. No surprise up-sells.
- Comfort All the Way: Premium fast trains, short internal flight, and 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: UMBRIA: 3 Days, 3 Nights
Villa located near Narni in Umbria
- TRIP FINALE: CALABRIA: 3 Days, 3 Nights
Tropea Delights with its Vantage Point on the Sea
Chapter 1: Arrival in Umbria
Italy's Green Heart —
3 Days, 3 Nights
DAY 1: ARRIVAL ROME AND TRANSFER TO UMBRIA
Your Journey begins with your arrival in Rome, where you are warmly welcomed and transferred into the peaceful landscapes of Umbria — Tuscany’s quieter, more soulful cousin.
As the city gives way to rolling countryside, vineyards, olive groves and ancient stone villages, the pace begins to shift. Upon arrival, settle into our Umbrian villa estate — secluded, timeless, and wrapped in the kind 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.
Welcome to Umbria Dinner — A Villa Evening
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 2: 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 3: 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 2: Calabria
The Bluest Waters —
3 Days, 3 Nights
DAY 4: 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 5: 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 6: 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 7: 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.