Siena’s brick-red charms, the vineyard waves of Chianti, the storybook hills of the Val d’Orcia—this condensed Tuscan escape distills our 7-day classic into five slow, flavor-filled days.
We keep you off the beaten path and far from the crowds, walking ancient strade bianche by day and lingering over farm lunches and trattoria dinners by night. Expect handcrafted pici, pecorino from the source, saffron stories, and Chianti Classico poured by the people who make it.
Private departures on any date
from € 2895 / person
4 nights in carefully selected hotels (3–4★), ensuite rooms
All breakfasts, 3 lunches, 4 dinners — local wine included with hosted meals
Private transportation throughout & luggage transfers
Dedicated local guide
Saffron experience or pecorino cheesemaking (according to availability)
Winery visit & tasting with the owner in Chianti
Hands-on cooking class
All entrance fees, taxes
Arrival/departure transport to/from start/end points; tips; 1 lunch on your own.
Meet at 4:00 pm, then wander Siena’s medieval lanes, Piazza del Campo, and a Palio contrada museum with our city expert.
Dinner at a beloved family trattoria—seasonal Tuscan plates and local reds.
A panoramic vineyard walk delivers us to Pacina, where the owner shares her natural winemaking philosophy. Farm-to-table lunch with estate wines.
Late-day cooking class in a historic setting—roll, sauce, taste, toast.
Short transfer to Bagno Vignoni; trail across soft hills to San Quirico d’Orcia. Long table lunch with handmade pici & truffles, plus an olive-oil tasting.
Free time among cypress-framed gardens; continue to Pienza.
Walk straight from the hotel into wheat fields and cypress lines. At Santa Maria Farm (or Il Casale, per availability) learn saffron craft or pecorino cheesemaking, then sit down to a rustic farm lunch.
Optional return walk. Farewell dinner in Pienza.
Morning transfer (≈45 min) to Chiusi–Chianciano Terme rail station for easy trains to Florence/Rome.
Note: Routes, sites, and activities may vary with seasons, special events, or weather—always to enhance your experience.
Art-nouveau villa just outside the medieval walls; quiet, elegant base a short stroll from the historic center.
Fresh, contemporary comfort on the edge of the Val d’Orcia’s iconic vistas; renowned staff and abundant breakfast.
This tour is as much a gourmet journey as it is a walking one: every farm, trattoria, and vineyard is carefully chosen for its authenticity.
Tuscan cuisine is the soul of this getaway. Every day brings a different taste of the region:
Hand-rolled spaghetti, hearty and rustic, usually dressed with cacio e pepe or wild boar ragù.
A refreshing salad of tomatoes, cucumbers, onions, and soaked bread—summer in a bowl.
Platters of prosciutto, salami, and crostini rubbed with garlic and drizzled in bright olive oil.
Wood-fired, served with rosemary potatoes and Chianti red.
From young and milky to aged and crumbly, paired with honey or fig jam.
Sangiovese at its best—structured, elegant, deeply Tuscan.
Coffee-soaked sponge with mascarpone cream, a sweet finale to a hearty Tuscan day.
La Villa Hotel, Viale Vittorio Veneto 11, Siena
4.00 PM
Chiusi – Chianciano Terme train station
10 AM
Light training helps—walk or jog 60 min, 3×/week for 5 weeks; add stairs if you live on flat ground.
Morning walk (≈3 hrs), long lazy lunch (≈1.5 hrs), short afternoon walk or village time. Back to the hotel by 4:30–5:00 pm; dinner in town (easy walk)
Plan a little cash for coffees/gelato; 1 lunch on your own.
Reliable walking shoes with grip, hat, swimsuit, sunscreen, reusable water bottle. No dress code for dinners. Walking sticks available.
Mild overall. Warm/dry in summer; spring & autumn are gentler; winter cooler but often sunny.
Optional and at your discretion.
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.
