Immerse yourself fully in Val d’Orcia, making cheese in the countryside and living the region from the inside, without having to manage a single logistical detail.
The Chianti region surprises in every season. But Val d’Orcia — the UNESCO World Heritage landscape stretching south of Siena — is something else entirely. Rolling hills, cypress-lined roads, thermal springs, and medieval villages where life moves at its own pace. This tour takes you deep into the heart of it: cooking traditional Tuscan food with a cookbook author, making pecorino cheese on a working farm, picking flowers at a hilltop garden run by three sisters, and soaking in thermal baths at Bagno Vignoni. You’ll taste Brunello di Montalcino at a small family winery, and every meal will be a celebration of what this land produces.
Tours
Dates
2026
October 26–30 (now open)
Also available anytime in Spring and Fall
(5 days and 4 nights)
Price (2026)
4 nights / 5 days
Single: $3,800
Double: $3,500 per person
Day-by-day itinerary
Day 1: Arrival and Introductions
Transfer from Florence with a private driver to our agriturismo in Val d’Orcia. Check-in and settle into our rooms. Meet our local guide in Pienza for a delightful stroll to discover the village, followed by aperitivo and dinner.
Day 2: Cook traditional Tuscan food
Head to the hills of Montepulciano for a cooking class with Pamela Sheldon Johns, author of the cookbook Cucina Povera. Pamela’s property has a 15-acre olive grove where she produces her own olive oil. As a certified olive oil sommelier, she will guide us through an olive oil tasting and a tour of her grove. We will cook several dishes together and enjoy lunch.
Visit Montepulciano with a local guide for a town tour, aperitivo, and dinner.
Day 3: Cheese Making Day
Drive to Pienza to meet Ulisse, owner and cheese maker of Podere il Casale. You’ll get to see all it takes to produce delicious raw pecorino cheese and enjoy a real farm-to-table lunch in one of the most beautiful locations of Val d’Orcia.
Free afternoon. Cozy dinner at the agriturismo.
Day 4: Flower Farm Experience
Drive to a beautiful flower farm run by three sisters. Each season brings something beautiful in the garden, making it a little corner of paradise! We will tour the farm, pick flowers, learn preservation techniques, and create a composition to take home. Enjoy lunch at the farm with local Tuscan products under a centuries-old olive tree.
Head to Bagno Vignoni, a tiny village with thermal baths. Relax in the hot springs and conclude the day with aperitivo and dinner at a local osteria.
Day 5: Wine Tasting & Departure
Drive to Montalcino, home of Brunello wine. Visit the town and then head to a small family farm for a wine tasting and lunch. Drive back to Florence.
Why you’ll love this tour
- Private transfer from Florence to Val d’Orcia and back
- Private driver throughout
- A host and local guides
- 4 nights in a beautiful agriturismo near San Quirico d’Orcia
- All meals: 4 breakfasts, 4 lunches, 4 dinners (wine included)
- All planned outings and experiences
Not included
- Airfare
- Travel insurance (highly recommended)
You’ll come away from this tour:
- Inspired by local farmers and makers
- Relaxed, recharged, and eager to return to your daily life with new energy
- Excited to share what you’ve learned in cooking and food preparation with your family and friends
- Appreciative of local wines, cheeses, and olive oil not only for their taste, but also for the stories about how and where they were produced
- Certain your slow tourism experience helped local farmers and artisans to live and prosper in the place they love
Giuditta was the perfect host for six magical days in Greve in Chianti. Time slowed down for me, my wife, and two kids, as we had beautiful, hands-on experiences with the makers of Greve. The truffle hunt/exuberant dog chase followed by shaving the truffles we found onto the pasta we made was a standout. A truly regenerative experience. Highly recommended! Anders G. Los Altos, California I was most impressed by Giuditta’s attention to detail. The agriturismo was a wonderful home away from home. All the activities were so well thought out—an incredible variety of experiences. The food and wine served at each of those events was superb! Carol G. New York State Giuditta is a perfect guide, an organizer par excellence. Her local knowledge of the region, its hidden and other secrets as well as her connections with the community all served to make our trip unforgettable. Ratna O. Toronto, CA Brilliant work by Giuditta coordinating our tour of Val d’Orcia! This is my first time traveling on an organized tour and it exceeded any expectations I had. Everything was taken care of for us. We loved the selection of activities, our friendly and knowledgeable guides and the pace of the week. Jodi G. New York State The goats, the goat farm, the natural surroundings, all the ancient buildings and traditions that are still in use, all together really went right into my heart and made me feel connected, as if I had belonged to that land in some past life. Golijeh Los Altos, California
