Step away from the crowds and journey into the green heart of Italy, where Umbria meets southern Tuscany. This 7-day tour unveils medieval towns, Etruscan treasures, enchanting landscapes, and unforgettable food. From Orvieto’s majestic cathedral to the mysterious Via Cava carved into volcanic rock, from the fairytale alleys of Pitigliano to the fortress of Sorano, every day reveals a secret corner of central Italy.
Food is always at the center of the experience: truffle dinners, lake cruises with farm-fresh lunches, wine tastings, tortelli pasta making class, olive oil press visit and cheese encounters at family farms. Every meal tells a story of the land and the people who keep traditions alive.
This is Italy far from the tourist trail—intimate, authentic, and deeply rewarding.
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6-night stay in two 4-star hotels, both in historic centers
All breakfasts, 5 lunches, 4 dinners – wine always included
Luggage transfer from hotel to hotel
Transportation during the tour
All entrance tickets and special events
1 local guide for groups 10 (group tours)
Tortelli pasta making at a family-run restaurant
Cheese-making and farm visit at an agriturismo
Olive oil tasting in Sovana
Boat cruise on Lake Bolsena with lunch onboard
All taxes
not included: transport to start & from end
not included: tips for guides and drivers
1 dinner and 1 lunch on your own
We begin in the medieval hilltop town of Orvieto. A guided stroll through cobblestoned lanes leads us to its Gothic cathedral, one of Italy’s greatest treasures. Evening brings a truffle-themed welcome dinner, paired with local wines.
Morning walk through Rocca Ripesena, famous for its rose gardens, before joining Luigi at his small vineyard for a memorable wine tasting and farm-to-table lunch. Evening visit to Civita di Bagnoregio, the “Dying City,” where dinner is served with magical views.
A leisurely walk along the tranquil shores of Lake Bolsena, followed by a private boat cruise across its shimmering waters. Lunch is served onboard with local specialties. Free evening to explore Orvieto and dine on your own.
We cross into Tuscany to explore Vitozza, an abandoned cave settlement hidden in the woods. Later, enjoy a wine tasting at Francesco Santori’s winery and settle into the hilltop town of Sorano. Free evening with plenty of charming trattorias to choose from.
Walk the ancient Via Cava San Giuseppe into Pitigliano, where alleys tell tales of the past. Elisabetta, a local guide, shares the moving history of the Jewish ghetto, “Little Jerusalem.” Tonight, we roll up our sleeves for a tortelli pasta-making class before a hearty dinner.
Walk the Etruscan Via Cava San Sebastiano and visit the Aldobrandesca Tomb. Olive oil tasting and light lunch at a local frantoio. Our grand finale takes place at Agriturismo Aia del Tufo, where we learn the art of cheese-making before a joyful farewell dinner.
Morning transfer back to Orvieto train station. A quick 90-minute train will have you at Rome’s airport.
A Renaissance palazzo once owned by the papal Piccolomini family, now a charming boutique hotel in the heart of Orvieto. History meets comfort in every corner.
A one-of-a-kind hotel set inside the medieval Orsini Fortress. Each room has its own character, with views over the green Etruscan valley or Sorano’s medieval village.
Throughout the week you’ll taste local wines (Orvieto Classico, Montecucco, Morellino di Scansano), seasonal vegetables from the volcanic soils, and timeless recipes that haven’t changed in centuries. It’s not just food—it’s the heart of Umbria and Tuscany on your plate.
Central Italy is a land where wine has been part of daily life for over two millennia. In Umbria and southern Tuscany, vineyards thrive on volcanic soils, sunlit hills, and the wisdom of winemakers who carry on ancient traditions. Each glass tells a different story—of earth, history, and passion.
Your first evening begins with one of Umbria’s culinary treasures: truffles. The earthy aroma fills the air as fresh truffles are shaved over handmade pasta or infused into creamy sauces. Paired with a glass of Orvieto Classico white wine, it’s the perfect welcome to the green heart of Italy.
The day we are by the lake of Bolsena we enjoy one of the best meals based on the local fish. Amazing receipes that you won’t find anywhere else
At a tiny vineyard near Rocca Ripesena, Luigi welcomes us as if into his own home. He serves his own wines alongside a rustic spread of pecorino cheese, prosciutto, and hearty lentil soups. The flavors are matched by his stories—each sip and bite connected to the land.
Roll up your sleeves for a hands-on cooking experience! Guided by a local chef, you’ll learn how to prepare pici pasta, long spaghetti with just flour and water. Then sit down together to enjoy the fruits of your labor, accompanied by a bold Tuscan red wine.
Extra virgin olive oil is liquid gold in this part of Tuscany. At a modern frantoio (mill), you’ll taste different varieties, drizzled over fresh bread, bruschette, and tomatoes. The peppery bite of a just-pressed oil tells you everything about the land’s richness.
Your journey ends with a joyous farewell dinner at a family-run agriturismo. Raffaella shows you how she makes pecorino cheese before serving a feast of fresh mozzarella, hearty ribollita soup, roasted meats, and garden vegetables. Homemade wine flows, and laughter fills the room—it feels less like a restaurant, more like a family table.
On this journey, wine isn’t simply a drink. It’s a connection to the land, to families who have cultivated these vineyards for centuries, and to the joy of sharing a table together.
Orvieto Classico (Umbria)
One of Italy’s most celebrated white wines, Orvieto Classico is fresh, mineral, and slightly fruity. Made from a blend of Grechetto and Trebbiano grapes, it pairs beautifully with lake fish, pecorino cheese, and pasta with truffles. You’ll sip it right where it’s made, in the rolling hills around Orvieto.
Sangiovese of Southern Tuscany
In this part of Tuscany, Sangiovese takes on a rustic, heartfelt character. Full-bodied and with notes of cherries, plums, and herbs, it’s the perfect companion to handmade tortelli, roasted meats, and hearty vegetable soups. Locals drink it as naturally as water at the dinner table.
Morellino di Scansano
Produced in the Tuscan Maremma, this red wine is vibrant and generous, with hints of blackberry and spice. It’s less famous than Chianti, but travelers often fall in love with its warmth and drinkability—especially when paired with pasta al ragù or pecorino cheese.
Montecucco DOC
This small but prestigious appellation lies between Montalcino and the Amiata mountain. Its wines, bold yet refined, are often compared to Brunello but with a wilder edge. A true hidden gem of the Tuscan south, best enjoyed in the company of locals who proudly pour it for their guests.
Vin Santo & Dessert Wines
To end on a sweet note, you may encounter Vin Santo, a golden, honey-like dessert wine traditionally served with crunchy cantucci biscuits. Dipping the almond cookies into the wine is not just allowed—it’s the tradition!
Roberto was born and raised in a small village on Amiata mountain, 50 miles south of Siena. Although his background is in biology he is very keen on traditions and history of Tuscany.
His passion is climbing. He is a climbing instructor and rescuer. Do not worry! He is happy to walk with you on flat terrain.
Roberto is definitely a people-person. He took several courses at “The Academy of Experiential Education” about “group dynamics”.
Native of Le Marche, Federico will capture your attention hunting for herbs that you can eat!
Music and foreign languages were the protagonists of his university studies, but for passion he has always devoted himself to animals, plants and landscape. You can see all his passion in the description of the small villages of Le Marche where he belongs to.
Price per person changes depending on the occupancy number of your private group.
More guests? Please ask us a quote. We can also tailor the tour to your needs.
| Number of guests | price in double room (euros) | single supplement (euros) |
| 1 | contact us | |
| 2 or 3 | 4990 | 420 |
| 4 or 5 | 3990 | 420 |
| 6 or 7 | 3690 | 420 |
| 8 or 9 | 3550 | 420 |
| 10 or 11 | 3450 | 420 |
| 12 or more | 3350 | 420 |
Orvieto
4.00 PM
Orvieto train station
10.30 AM
walking/jogging 3x per week before departure recommended
walking shoes with traction, sun hat, sunscreen, refillable bottle, swimsuit, casual dining clothes
mild in spring/fall, hot in July/August but breezy on the hills
morning walk (2–3 hrs), long lunch with wine, optional stroll/town visit in afternoon, rest, then dinner in town or farmhouse
1–18 guests
no limit
My husband and I spent 7 days in September walking the Tuscan Hills with Gianni and Rudy. As I read my journal from our trip almost 3 months ago it brings a smile to my face as I relive those treasured moments of hiking beautiful vineyard hillsides, making pasta at a local restaurant, listening to arias from well known Italian operas, drinking glorious wines with local wine makers, eating fabulous foods, learning about making cheese, doing yoga in a beautiful vineyard and listening to Gianni play his flute.Gianni’s organizational skills and ability to relate to all his guests was a large part in making this trip so memorable and enjoyable.
The Best Way to See Italy Forget Rick Steves and sign on with Gianni for a wonderful exploration of some of the best Italy has to offer–countryside, history, food, and people. Gianni’s deep knowledge of all these adds so much richness to the experience of walking through picturesque medieval towns and gorgeous rolling hillsides of vineyards, fields and orchards. The accommodations were comfortable and centralized, often with wonderful views.Although this was a tour through the areas surrounding Siena, Montalcino and Pienza, Gianni offers tours in other areas and I would expect the same high level of engagement and effort to provide unique experiences. Truly exceeded my expectations!
Walk about Tuscany Loved this tour and would highly encourage others to go. Our guides Gianni and Sara were great, everything ran smoothly from day one. Excellent choices of hotels, restaurants and walking trails. The perfect size group, lots of laughs and good memories. Looking forward to the next one. Grazie, Monica
Under the Tuscan Sun…and a big black cloud but only once I have just returned from 8 fabulous days with Walk About Tuscany hosted by Gianni and Rudy and helped by their hard working transportation crew who ensured we were picked up on time, we traveled safely and no luggage was lost. We had many moments of fun and laughter and even a couple of flute recitals just for a change of pace!! In the end, I have Gianni to thank for this experience. His thoughtful organization and attention to detail were key in delivering a superb product, a memorable adventure and a trip of a lifetime. Walk About Tuscany is highly recommended! Grazie, Gianni
The unforgetable Tuscany I am so amazed with Gianni who operated our tour with his in-depth knowledge of every single steps and buildings around Tuscany. Not to mention his creativeness in every moments of our walks. You will have great lunches and dinners with lots of special-2-thumbs-up wines. We also visit Olive Oil producer and given sampler at which is the best (and fresh) olive oil that I had ever tasted ! The scenery view is very awesome, just like the post card. Highly recommended and wouldn’t mind to do this tour again.
Group Tour of Tuscany Hill Towns with Walk About Tuscany Tours I had a marvelous time on this trip. Our guide, Gianni, provided gorgeous walks and unique experiences with local organic producers of wine, produce, cheese, and olive oil. Definitely experiences I couldn’t have had without his guidance and that helped me to appreciate what makes this region unique. Gianni is knowledgeable and expended every effort to ensure that our trip was memorable and unique. We walked, ate very well, drank wonderful wines and learned a great deal about this region of Tuscany and why it is among the most delightful of all Italy.
Terrain: Mostly flat or gently rolling terrain, with well-maintained paths and only occasional short uneven sections.
Distance: Usually shorter walks, around 4.5 to 5.5 km / 3 to 4 miles per day, depending on the itinerary.
Elevation gain: Very limited. There may be a few gentle slopes, but no significant climbs or descents.
Who it is for: Ideal for beginners, casual walkers, families, and anyone looking for a relaxed walking holiday with little physical effort.
Terrain: A mix of flat sections and more uneven ground, with some inclines, steps, or minor obstacles that remain manageable for most reasonably active travellers.
Distance: Generally around 5 to 8 km / 3 to 5 miles per day, depending on the tour and terrain.
Elevation gain: Noticeable but not demanding. Some uphill and downhill stretches may be present, though never steep or prolonged.
Who it is for: Suitable for beginners who want a slightly more active experience, as well as for regular walkers looking for a relaxed but rewarding pace.
Terrain: Varied terrain that may include uneven paths, longer walking sections, and regular uphill or downhill stretches.
Distance: Moderate daily walking time and distance, suitable for travellers who enjoy being active outdoors for a good part of the day.
Elevation gain: More consistent and clearly noticeable, though still within the reach of anyone with a basic to good level of fitness.
Who it is for: Best for active travellers who are comfortable walking for several hours a day and can handle some uneven terrain and sustained inclines.
