A Journey Through Italy's Heart
From the hilltop charm of Orvieto to the hidden gems of Umbria and southern Tuscany, discover a rich tapestry of art, history, and authentic flavors in Italy’s most soulful landscapes.
From the medieval heights of Orvieto to the quiet beauty of Umbria and southern Tuscany, this immersive journey reveals Italy’s timeless charm through art, history, and heartfelt hospitality. You’ll explore ancient hilltowns, visit celebrated wineries, uncover Renaissance masterpieces, and savor refined local cuisine—often shared in intimate, family-run settings. With elegant boutique accommodations, expert local guides, and plenty of time to embrace the slower pace of Italian life, this experience offers the perfect blend of cultural depth, culinary pleasure, and genuine connection.
Tour is limited to 15 guests
Travel dates
21st May - 27th May 2026
Price
€4.500 per person, double occupancy
Single supplement €650
Itinerary
Orvieto - Civita di Bagnoregio - Pitigliano - Montalcino - Pienza - Perugia - Montefalco - Bolsena
Day 1 - Benvenuti a Orvieto
Upon your arrival at Rome, you will be met and transferred privately to Orvieto, the hilltop town that will be our base for the week.
After check-in, the afternoon is yours to relax and settle in. Enjoy a light lunch, rest after travel, or take your first independent stroll through Orvieto’s medieval streets, where stone alleyways, artisan shops, and sweeping views offer an immediate sense of place.
In the late afternoon, we will meet for a private guided tour of Orvieto. Together we’ll explore the historic center, visit the magnificent Duomo, and descend into the fascinating underground city carved into volcanic rock, uncovering the layered history beneath our feet.
In the evening, we will gather for our welcome dinner in town. Over regional cuisine and local wines, we’ll begin our journey together in a relaxed and convivial atmosphere.
Day 2 – Flavors of Orvieto & An Evening Among the Vines
Late in the morning, we gather in Orvieto for a relaxed tasting experience that introduces the wines and regional flavors of the area, paired with local specialties.
The afternoon is yours to enjoy at your own pace, whether exploring the town, lingering in a café, or returning to the hotel to rest.
In the afternoon, we’ll invite you to visit Madonna del Latte - our family winery that’s also our home. You’ll join us for a personal tour through the sun-kissed vineyards, the bustling fermentation cellar, and the extraordinary ancient Etruscan barrel cellar carved deep into volcanic rock. The visit culminates in a carefully curated, elegant wine tasting dinner held in the intimate, inviting setting of our winery-home. Here, you’ll savor the estate’s finest wines, thoughtfully paired with seasonal dishes, all served in a warm, inviting atmosphere that reflects our family’s passion for sharing the true flavors and traditions of Italy.
Day 3 – Slow Morning in Orvieto & Hilltop Wonders Beyond
This morning is yours to enjoy Orvieto at your own rhythm. You might browse the farmers market, return to the Duomo, explore artisan workshops, linger at a café, or simply soak in the atmosphere of this timeless hilltop town.
In the early afternoon, we set off for Civita di Bagnoregio, the breathtaking “Dying City,” dramatically perched above a canyon and reached only by a pedestrian bridge. You’ll have time to wander its quiet stone streets and take in its extraordinary setting.
From there, we continue on a scenic drive toward Pitigliano, with views stretching across the countryside and toward Lake Bolsena. Upon arrival, there will be time to stroll through the historic center and admire the panoramic viewpoints over the golden tufa cliffs before we gather for dinner together.
As evening settles, we sit down for a traditional meal in town, enjoying the bold, earthy flavors of southern Tuscany in one of Italy’s most striking hilltop settings.
Day 4 – Art, Architecture & Bold Wines in Umbria
Our day begins in Perugia with a guided visit to the renowned Galleria Nazionale dell’Umbria, home to an extraordinary collection of medieval and Renaissance masterpieces. Through these works, we trace the artistic soul of the region and the legacy of painters such as Perugino.
From there, we continue to Montefalco for a private visit to a family-run winery. Here, we explore the depth and character of Sagrantino, Umbria’s most powerful and expressive wine, accompanied by a light lunch featuring regional specialties.
In the afternoon, we visit a striking contemporary winery, where architecture and landscape merge in dramatic form. A guided tour and tasting offer a fascinating contrast between tradition and modern vision.
Day 5 – The Wines of Montalcino & the Charm of Pienza
This morning we journey through the rolling landscapes of the Val d’Orcia into the heart of Tuscan wine country. In Montalcino, we enjoy a private visit to a celebrated winery, where we explore the cellars and discover how the region’s renowned Brunello is crafted. A guided tasting is followed by lunch at the winery’s own restaurant, featuring traditional Tuscan cuisine and sweeping countryside views.
In the afternoon, we continue to Pienza, the Renaissance “ideal city.” During our guided visit, we stroll through elegant piazzas and panoramic viewpoints, and stop at a local bottega to taste the town’s famous pecorino cheese.
Evening at your leisure for dinner, perfect for returning to a favorite spot or discovering something new.
Day 6 – Lago di Bolsena: Vines, Waters, and a Farewell Feast
We begin the day with a relaxed lunch overlooking the shimmering waters of Lago di Bolsena, paired with the elegant Syrah from Podere Monte Landro and a selection of local bites, all enjoyed with sweeping views of the lake and rolling hills.
In the afternoon, we’ll take to the water for a tranquil boat tour across Europe’s largest volcanic lake, gliding past the islands of Bisentina and Martana, where nature and legend intertwine.
As the sun begins to set, we’ll gather for a farewell dinner at a stunning lakeside restaurant built on stilts above the water. With the lake reflecting the colors of dusk, we’ll toast to the journey behind us with unforgettable food, wine, and company.
Day 7 – Arrivederci
Savor your final breakfast in Orvieto, taking in the quiet charm of this hilltop town one last time. As the journey draws to a close, you’ll check out from the hotel and begin your onward travels.
Whether you're heading to Rome, extending your stay elsewhere in Italy, or returning home, we’re happy to assist with arrangements.
What's included
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Transfer from Rome Fiumicino Airport to hotel in Orvieto
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6 nights in carefully selected boutique 4-star hotel with daily breakfast
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Four dinners, including an exclusive wine tasting dinner at Madonna del Latte Winery and a lakeside farewell feast
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Exclusive, relaxed lunch featuring Syrah from Podere Monte Landro paired with panoramic views of the lake
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Winery visits and tastings in Montalcino and Montefalco, including two guided lunches
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Private guided tours with expert local guides in Orvieto, Civita di Bagnoregio, Pienza, Perugia, and Montefalco
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Entrance fees to scheduled landmarks and sites
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All ground transportation during the tour by private, air-conditioned coach
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Scenic boat tour on Lago di Bolsena with wine aperitivo
What's not included
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Flights to and from Italy
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Transfer from Orvieto to the airport (last day)
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Travel insurance (recommended)
Is This the Right Trip for You?
This trip offers a rich blend of cultural exploration, wine experiences, and scenic walks. Here’s what you can expect:
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Visits to cultural and historic sites with guided tours
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Walking is a significant part of the experience, including navigating uneven surfaces and cobblestone streets
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You’ll enjoy authentic local dishes and wines - this experience is ideal for travelers eager to explore genuine regional flavors
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Small group setting offering a cozy, personal atmosphere
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Perfect for travelers eager to explore authentic Italy beyond the usual tourist paths
Your Hosts on This Journey
We are Ruta and Leon, your hosts and the family behind Madonna del Latte.
Many of you have already shared a glass of wine with us at our table, and now we’re inviting you to travel further together.
We can’t wait to guide you through Italy the way we know it and live it - with the same spirit, care, and passion that shape our days at the winery and in our travels.