Tuscany is world-famous — but most travelers only see the crowded squares of the main art towns, rushing from one stop to another. With us, you’ll step off the beaten path. Our gentle walks (2–3 hours each morning) take you into the vineyards, olive groves, and medieval towns where life still moves slowly.
This is also a culinary journey: at lunchtime we are welcomed into farmhouses run by families who have lived here for generations, serving meals made from their own produce and poured with their own wines. In the evenings, we dine in hand-picked restaurants right in the historic centers where we stay — trattorie loved by locals, osterie with stories, menus full of Tuscan character.
From Siena to Chianti, San Gimignano to Pienza, every step brings us closer to Tuscany’s timeless landscapes — and every meal celebrates its flavors. Expect wines poured by the producers themselves, handmade pasta rolled under your eyes, truffles shaved on your plate, and desserts that carry the essence of Italian dolce vita.
It’s not just a walking tour. It’s Tuscany experienced through its flavors, its landscapes, and its people — always away from the tourist crowds.
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6 nights in charming, family-run hotels (3–4 stars, some with views if booked early)
All breakfasts, 5 farmhouse lunches, 4 dinners in authentic local restaurants (wine always included)
Transportation during the tour + luggage transfers
Groups of up to 9 guests are led by 1 local guide / Groups of 10 guests or more are led by 2 local guides
Farm visit in Pienza: saffron fields or pecorino cheese making, with lunch
Winery visit in Chianti with tasting & lunch hosted by the owner
Entrance tickets to special sites
Olive oil tasting: learn how to tell a great Tuscan EVOO
Full cooking class in a historic Tuscan kitchen
All local taxes
not included: transport to/from start & end
not included: tips for guides
not included: 2 dinners on your own
At 4:00 pm we meet at La Villa Hotel in Siena. Our first steps take us into the medieval heart of the city with an art guide: Piazza del Campo, and the secrets of the Palio horse race. Dinner is at Babazuf, a family-owned restaurant where Chef Giovanni reimagines Tuscan classics.
We walk among the vineyards of Chianti before arriving at Pacina Farm, where Giovanna serves us a meal entirely from her land, paired with her family’s natural wines. In the evening, a hands-on cooking class at the Dante Alighieri cooking school — fun, flour-dusted, and delicious.
A short transfer brings us to San Gimignano, its medieval towers rising above the hills. We walk through Vernaccia vineyards and olive groves before reaching the Ganozzi family farmhouse, where a garden-to-table lunch awaits. Back in Siena, dinner is on your own — plenty of trattorie to choose from.
We stroll the cobblestones of Montalcino before a woodland walk with sweeping views of Monte Amiata. At Giacomo’s Il Cocco farm, we taste Brunello with the winemaker and sitdown to a farmhouse lunch. Evening transfer to Pienza, where dinner is served in one of its best trattorie.
We visit Bagno Vignoni’s hot springs, then walk to San Quirico. Lunch at Osenna features handmade pici pasta with truffles and an olive oil tasting. Afternoon to explore the town’s gardens and streets. Dinner on your own in Pienza, with many inviting options.
We walk to Monticchiello through wheat fields. Depending on the season, we either visit Santa Maria Farm for saffron or Il Casale for pecorino making, followed by a farm lunch. Tonight, our farewell dinner is a refined Tuscan fusion menu — a perfect finale to our gourmet journey.
After breakfast, transfer to Chiusi–Chianciano Terme station for trains to Florence or Rome.
Art nouveau villa just outside Siena’s walls. Elegant rooms, friendly staff, walking distance to the old city.
Modern 4-star hotel with panoramic Val d’Orcia views and hearty breakfasts. A perfect base to enjoy Tuscany’s southern heart
Every meal is part of the journey — not a pause, but a highlight.
handmade pasta, saffron risotto, pecorino cheese, vegetables straight from the garden, wines poured by the winemakers themselves.
carefully chosen restaurants in Siena and Pienza, where locals gather and every dish tells a story
Chianti Classico, Vernaccia, Brunello di Montalcino, Vino Nobile di Montepulciano, Orcia DOC
handmade tiramisù and other Tuscan desserts.
Every meal is part of the journey — not a pause, but a highlight.
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 |
Siena – La Villa Hotel
4.00 PM
Chiusi – Chianciano Terme train station
10 AM
light training before departure helps enjoy the walks.
included with every meal — not just “house wine” but the pride of each region we visit.
2 dinners on your own (~€20–25), daily coffees (€5).
mild, best in spring & autumn.
morning walk (2–3h), rich farmhouse lunch, optional stroll or town visit in the afternoon, evening dinner in town restaurants.
1–18 guests
no limit
can be combined with other Walk About Italy tours
farmhouse lunches & historic town dinners
away from tourist crowds
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.
