The Chianti region surprises in every season, with rolling hills, olive groves, vineyards, villas, and medieval hamlets stretching between Florence and Siena.
It’s world-famous for its wine. But you’ll experience much more with us. This 7-day tour features lovely walks through olive groves and vineyards and visits to medieval hamlets. You’ll connect with local makers and crafters, and get the chance to make food with your own hands. You’ll enjoy amazing local food in farmhouses and trattorie. From truffle hunting in oak woods with adorable dogs to making goat cheese on a small farm, from exploring Florentine artisan workshops to tasting wine at a one-man hilltop winery — this is Chianti from the inside.
Tours
Dates
2026
June 23–30
September 1–8
Price (2026)
7 nights / 8 days
Starting at $4,000
5 nights in Greve in Chianti, 2 nights in Florence
Day-by-day itinerary
Day 1: Settle in at the farmhouse
Pick up from Florence airport or train station and transfer to a beautifully renovated farmhouse in the middle of vineyards in Greve in Chianti. Aperitivo in the garden, get to know each other, and dinner at the villa.
Day 2: Explore the medieval hamlet
After a delicious breakfast, a guided walk among the hills to explore an artist’s residency in a 12th-century building and lunch in a family-run farmhouse.
Day 3: Meet the winemaker
Visit a one-man organic winery nestled on top of a hill. Experience his work and taste his wines in the comfort of his home.
Day 4: Truffle hunting in the oak woods
Head to the truffle hunter’s home and get ready for the truffle hunt with two adorable dogs. After collecting truffles in the oak woods, head back to make a delicious lunch together of fresh pasta and truffles.
Day 5: Cheese making
Visit a small goat farm. After milking the goats, make cheese together in the workshop. You’ll get a new appreciation for goat cheese! Lunch at the farm, then head back to the villa to relax.
Day 6: Florence & artisan workshops
Head to Florence to explore the Oltrarno neighborhood, filled with incredible hidden art workshops. You’ll see Florence through new eyes. Dinner in a trattoria.
Day 7: City tour with art historian
Tour of Florence with an art historian who brings the city’s stories to life. Last dinner together in a trattoria.
Day 8: Arrivederci
Breakfast and transfer to Florence airport or train station.
Why you’ll love this tour
- 7 nights accommodation (5 in Greve in Chianti, 2 in Florence)
- 7 breakfasts, 5 lunches, 6 dinners (wine included)
- All activities in the itinerary
- Private local guides
- Transfer on private car/minivan with driver from and to Florence Airport, from Greve to Florence and for all outings
Not included
- Airfare
- Travel insurance (highly recommended)
- Everything else outside what’s mentioned in the itinerary
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
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 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 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 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
