Overview
Tuscany and Umbria make their point gradually. In Siena, daily life still bends around the Piazza del Campo and the rivalries between the contrade that shape the city from within. Further south, the Val d’Orcia opens into hill towns, vineyards, and fields rooted in galestro, where the landscape feels cultivated rather than staged.
In Umbria, Montefalco brings stone, Sagrantino, and a quieter rhythm. From truffle hunters and raw-milk cheesemakers to handmade pasta and a rare visit with Giampiero Bea, this journey moves through a world of craft, knowledge, and trusted local access. By the end, what lingers is not just the beauty of Central Italy, but the sense of how these places still live.
What to expect: wine, truffle, long tables, and countryside charm.
Season: March to mid June & mid September to end October
Highlights
- Walk Siena through its medieval contrade and the Piazza del Campo.
- Taste pecorino in Pienza and Vino Nobile in Montepulciano’s vaulted cellars.
- Settle into Chianti Classico and a family-style feast with Dario Cecchini.
- Spend time at Quinto Sapore, where cooking and harvest still belong together.
- Head into the Umbrian mountains for a truffle hunt and a rustic village lunch.
- Visit cloistered Trappist Sisters whose organic wines are rarely seen from this close.
Gallery
Testimonials
What an amazing, beautifully curated trip!! Gorgeous places, generous and gracious people, and gastronomical genius! Cannot wait to explore more!
Alice made our trip unforgettable. She truly listened to what we wanted, adjusted plans with care, and made everything seamless. Her timing was perfect — always checking in just when needed. The guides felt like old friends, and every hotel, restaurant, and activity was spot on. We couldn’t have asked for a better experience!
The total program was perfect including itinerary, guides, lodging, transportation,and food choices. Your recommendations and guidance was spot on!
We had an incredible trip! We are leaving with full hearts and endless memories. Thank you for being a constant source of help and information. The level of service we received from you was truly one of the biggest highlights from our trip. And the care each hotel put into receiving our children was heartwarming. I’m so grateful for you and all your attention to detail. Thank you for crafting such a well executed adventure for me and my family!
Authentic is the correct one word description. The tour guides were fantastic, and really portrayed to the local society tremendously. Thank You for a Great trip !!!
