A true small group
This limited series is capped at eight guests, creating a more intimate and flexible journey.
Now Journey Limited Series
Italy's Hidden Chapters
A slower journey through Umbria's green heart and Calabria's luminous coast.
Rome arrival → Umbria → Tropea, Calabria
- 7 days / 6 nights
- Maximum 8 guests
- Tour Captain hosted
- Villa & coastal stays
- 50+ five-star reviews
From $6,979per person, double occupancy+ $250 required internal airfare per guest
No obligation. No pressure. Just a thoughtful conversation about your Italy.
7 Days / 6 NightsUmbria + Calabria
Maximum 8 GuestsLimited Series
Two Distinct StaysUmbrian villa + Tropea coast
Slow TravelGuided discovery + meaningful leisure
Italy beyond the icons
The quieter Italy people hope still exists.
Italy's Hidden Chapters is designed for travelers who have already seen the icons and are ready for what comes next: hill towns, olive groves, villa evenings, coastal lanes, crystalline water, and the pleasure of traveling at a more human rhythm.
From your arrival in Rome, we transfer into Umbria—a land of stone villages, quiet landscapes and soulful traditions—before continuing south to Tropea, one of Italy's most beautiful seaside towns.
“This is not a rushed checklist. It is Italy experienced slowly—with the details handled and time left to truly be there.”
The Hidden Chapters design philosophy
Your Journey Ahead
Two Italian chapters. One beautifully unhurried story.
From a secluded Umbrian villa to the blue Tyrrhenian Sea, the journey moves south with purpose—and never in a rush.
- 01 Umbria Hill towns, olive groves, long lunches and the calm of a countryside villa near Narni.
- 02 Tropea, Calabria Clifftop lanes, crystalline water and the bold, sun-washed flavors of Southern Italy.
Is this journey right for you?
Hosted, personal and intentionally unhurried.
A maximum of eight guests changes the texture of the experience: easier movement, more personal attention, more relaxed meals and fewer moments spent waiting for a crowd.
Room to breathe
Guided mornings are balanced with meaningful leisure, including two intentionally open days.
Tour Captain hosted
Your Tour Captain coordinates transitions, offers recommendations and keeps the practical details moving smoothly.
No big-bus feeling
Private transfers, a short internal flight and appropriately sized premium vans replace conventional coach-tour machinery.
Leisurely walking
Sightseeing typically includes 45 to 90 minutes of walking, with stops and opportunities to opt out.
Best for curious travelers
Ideal for guests who value culture, local flavor, beautiful stays and discovering Italy beyond its famous icons.
Still deciding whether the pace feels right?
Ask Us Anything
Speak directly with our team about walking, leisure, flights, room preferences or anything else on your mind.
What's included
The details are handled. The discoveries still feel yours.
From your Rome welcome to luggage handling, privately guided discovery and hosted dining, the journey is designed to feel seamless without feeling over-scheduled.
Not included: International airfare, optional experiences and the Tour Captain gratuity. A required on-tour airfare charge of $250 per guest is due with the deposit.
Your Tour CaptainFriendly, entertaining hosting from beginning to end.
Six hotel nightsThree nights in an Umbrian villa and three nights at a coastal Tropea hotel, with breakfast.
Private guidingEasy-to-understand local guides and signature Discovery Walks.
Arrival welcomeMeet and greet in Rome followed by the planned transfer to Umbria.
Planned transportationPrivate transfers, a short internal flight and appropriately sized premium vans. No large buses.
Luggage portageHandling through the journey without surprise upsells.
Regional diningItinerary-listed dining with unlimited premium beverages where specified.
Transparent pricingCity taxes and planned gratuities included, except for the Tour Captain.
Explore the Complete Journey · Umbria to Calabria
The Complete Itinerary
Seven days unfold as two connected Italian stories: first the green, contemplative center of the country, then the bright edge of the Tyrrhenian Sea.
Chapter One
Days 1–3
Umbria
Italy's green heart—stone villages, olive groves, villa evenings and the permission to slow down.
Italy grows quieter here.
Umbria is the opening exhale: an arrival through rolling countryside, days shaped by stone lanes and local flavor, and evenings that return you to the stillness of a villa.
Day 1
Rome arrival 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, settle into the Umbrian villa estate: secluded, timeless and instantly grounding.
Included Today
- Rome meet and greet
- Transfer to the Umbrian countryside
- Welcome to Umbria orientation
- Villa welcome dinner
Day 2
Umbria's quiet magic
Explore a storybook hill town, wandering medieval lanes and discovering hidden piazzas where centuries of life have unfolded. Continue with a local olive oil or wine estate visit and a long, leisurely regional lunch.
The afternoon returns you to the villa for unstructured leisure—time to rest, wander the grounds or simply enjoy the stillness.
Included Today
- Hill-town exploration
- Olive oil or wine estate experience
- Long regional lunch
- Village dinner hosted by your Tour Captain
Day 3
A day of choice
Today is intentionally unscheduled—a rare gift of time to follow your own curiosity or simply be still. Possibilities may include a hands-on cooking class, seasonal truffle hunting, a relaxed day trip to Assisi, Spello or Montefalco, or a full day at the villa.
Tonight, gather for a chef-prepared farewell to Umbria dinner using seasonal ingredients and time-honored regional recipes.
Included Today
- Open day for independent plans or rest
- Tour Captain recommendations
- Chef-prepared farewell to Umbria dinner
Where You Stay
Your Home in Umbria
An Umbrian countryside villa from the Now Journey Hotels Collection or similar. This three-night stay is chosen for its quiet setting, panoramic views and the slower rhythm that lets the first chapter feel rooted in place.
Stay profile: Three nights with breakfast included; final property details are confirmed with your proposal.
“The right Umbrian stay should make the countryside part of the Journey—not something viewed through a bus window, but something you wake up inside.”Hotel Note
Chapter Two
Days 4–7
Calabria
The blue-water finale—clifftop Tropea, coastal lanes and Southern Italy at its most elemental.
The Journey turns toward the sea.
Calabria changes the light and the pace. Tropea's cliffs rise above clear water, guided discovery gives way to coastal leisure, and the Journey finishes with room to savor where you have arrived.
Day 4
To the coast
Transfer to Rome and board a short flight south to Calabria. On arrival, continue by private transfer to Tropea, a luminous coastal town of honey-colored cliffs and turquoise water.
After settling in, step out for a Discovery Walk through Tropea's dramatic clifftop setting and winding lanes, followed by a welcome dinner celebrating the flavors of Calabria.
Included Today
- Planned transfer to Rome
- Short internal flight to Calabria
- Private transfer to Tropea
- Discovery Walk and welcome dinner
Day 5
Exploring Tropea
With a local expert, explore Tropea's historic heart: palazzi, hidden chapels, flower-draped balconies and viewpoints over the Tyrrhenian Sea and Santa Maria dell'Isola.
The afternoon is at leisure. Tonight, join the Tour Captain for an optional dinner or explore independently.
Included Today
- Expert-guided walking tour
- Historic center and scenic viewpoints
- Open afternoon
Day 6
Leisure on the coast
Another intentionally unscheduled day offers time for a Calabrian cooking experience, savoring regional flavors, exploring independently or simply resting by the sea.
Tonight, gather for a chef-prepared farewell dinner drawing together Calabria's coastal bounty and time-honored recipes.
Included Today
- Open day for independent plans or rest
- Tour Captain recommendations
- Farewell dinner
Day 7
Arrivederci, Italy
Breakfast is included this morning should you have time before departure. Lamezia Terme International Airport (SUF) is approximately one hour from Tropea.
The departure airport transfer is optional and not included. The Now Journey team can provide guidance or help arrange it with your confirmed journey plans.
Included Today
- Breakfast, subject to flight timing
- Departure guidance from the Now Journey team
Where You Stay
Your Home in Tropea
Hotel Rocca Della Sena or similar from the Now Journey Hotels Collection. This three-night coastal stay is selected for its refined setting, panoramic sea views and easy relationship with Tropea's historic center.
Stay profile: Three nights with breakfast included. The photograph shows Tropea's coastal atmosphere; your confirmed property is detailed in your proposal.
“Tropea should remain present even after the day's discoveries end: sea air, changing light and the pleasure of knowing the coast is still just outside.”Hotel Note
Thoughtful planning. Personal care. A much smaller group.
50+ Five-Star ReviewsIndependent Tripadvisor feedback
American-Owned & OperatedColorado based
Maximum 8 GuestsThis Limited Series
2027–2028 Limited Departures
Choose your Hidden Chapters departure.
Prices are in US dollars, per person based on two guests sharing a room. International airfare is not included.
September 25–October 1
Hosted with Mark Story
$6,979Deluxe · per person, double occupancy
Required internal air: $250 per guest
Deposit due: $1,000 tour deposit + $250 internal air
May 1–7
Limited to 8 guests
$6,979Deluxe · per person, double occupancy
Required internal air: $250 per guest
Deposit due: $1,000 tour deposit + $250 internal air
September 12–18
Limited to 8 guests
$6,979Deluxe · per person, double occupancy
Required internal air: $250 per guest
Deposit due: $1,000 tour deposit + $250 internal air
Transparent deposit: $1,000 tour deposit plus the required $250 internal airfare, for $1,250 per guest total at deposit.
Prefer another date? Request a proposal and tell us the season that works best. We will help you explore the possibilities without pressure.
Frequently asked questions
A few things travelers ask first.
How many people are on this tour?
Italy's Hidden Chapters is a limited series capped at a maximum of eight guests. That smaller size supports more personal hosting, easier movement and a relaxed group dynamic.
How active is the journey?
The sightseeing pace is leisurely, with approximately 45 to 90 minutes of walking on many touring days. Historic lanes may include uneven surfaces, hills or steps, but there are regular stops and opportunities to opt out.
How much leisure time is included?
Leisure is an intentional part of the design. Guided discoveries are balanced with open afternoons, and Days 3 and 6 are purposefully unscheduled so you can follow your curiosity or simply rest.
Is this a large bus tour?
No. Planned transportation uses private transfers, a short internal flight and appropriately sized premium vans. The experience is designed for a maximum of eight guests, not a large motorcoach group.
Are optional experiences included?
Optional cooking classes, seasonal truffle hunting and independent day trips are suggestions for open time and are not included unless specifically confirmed in your proposal.
How do the hotels work?
The journey uses hand-picked 4+ to 5-star properties, including an Umbrian countryside villa and a coastal Tropea hotel. Named properties are examples and may be replaced with a comparable property when necessary.
Your Journey Begins Here
Can you picture yourself in this quieter Italy?
If Umbria's hill towns and Calabria's luminous coast feel like the Italy you have been hoping to experience, we would be honored to help you begin.