
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 Fiumicino Airport (FCO), you’ll be warmly welcomed and transferred by private coach to Orvieto. Once there, you’ll check in at the elegant ****Emme Palace Hotel & Spa, a stylish and serene retreat in the heart of this historic hill town.
Take some time to settle in, unwind, and perhaps enjoy a stroll through the nearby streets before our first evening together.
As the sun begins to set, we’ll gather in the hotel’s bar area for a relaxed welcome aperitivo - a chance to connect with your fellow travelers and toast to the start of our journey. From there, we’ll head out for our first group dinner at one of Orvieto’s cozy, locally loved trattorie, where good wine, seasonal dishes, and conversation will ease us into the rhythms of the days to come.

Day 2 – Orvieto’s Hidden Gems & an Evening Among the Vines
This morning, our licensed local guide will lead us through Orvieto’s most iconic landmarks, including the breathtaking Duomo. After the guided tour, you’ll have free time to explore Orvieto at your own pace—whether that means browsing local shops, enjoying a relaxed lunch, or simply soaking up the atmosphere of this hilltop gem.
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 return to favorite spots like the Duomo, browse artisan workshops, linger at the farmers market, or simply sip a coffee in a quiet piazza and watch the town come to life.
In the early afternoon, we’ll set off with our local guide for an excursion into the dramatic landscapes beyond Orvieto. Our first stop is the breathtaking Civita di Bagnoregio, known as the “Dying City,” perched high above a canyon and accessible only by a pedestrian bridge. Its crumbling beauty and otherworldly setting make it one of Italy’s most unforgettable sights.
From there, we’ll take a scenic drive past the shimmering waters of Lake Bolsena, eventually arriving in Pitigliano - a striking hilltop village carved from golden tufa stone, where layers of Etruscan and medieval history blend seamlessly into the cliffs. As the sun begins to set, we’ll gather for a delicious traditional dinner in a trattoria nestled in the town’s main piazza, enjoying the bold, earthy flavors of southern Tuscany in this unforgettable setting.

Day 4 – The Wines of Montalcino & the Charm of Pienza
This morning we’ll journey into the heart of Tuscan wine country for a guided visit to a celebrated winery in Montalcino. We’ll explore the vineyards and cellars, discover how the region’s world-renowned Brunello is crafted, and then enjoy a guided tasting of the estate’s finest wines paired with a relaxed lunch featuring local specialties.
In the afternoon, we’ll continue through the scenic Val d’Orcia to Pienza, a Renaissance treasure known for its harmonious architecture, sweeping views, and the unmistakable scent of pecorino cheese drifting from its artisan shops. A guided stroll will introduce us to its beauty and history before we head back to Orvieto.
Evening at your leisure for dinner, perfect for returning to a favorite spot or discovering something new.

Day 5 – Art, Architecture & Bold Wines in Umbria
Our day begins in Perugia with a visit to the recently reopened Galleria Nazionale dell’Umbria, home to an extraordinary collection of Italian medieval and Renaissance art. The collection features many masterpieces, including works by the celebrated Umbrian artist Perugino.
From there, we continue to Bevagna, where contemporary design meets ancient craft at a striking winery created by renowned sculptor Arnaldo Pomodoro. We’ll tour the winery and enjoy a tasting of Montefalco Sagrantino, one of Umbria’s boldest and most expressive wines.
In the afternoon, we travel to nearby Montefalco to admire the stunning frescoes of Benozzo Gozzoli in the Church of San Francesco - vivid stories painted in radiant color that bring the past to life.

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