You’ll walk medieval streets in Monteriggioni and San Gimignano with a local guide, taste homemade Tuscan dishes (and Vernaccia wine) at a family farm lunch, watch alabaster artists at work in Volterra, and have time to explore each town’s corners your own way. Expect laughter over lunch and moments that stick with you long after you’re home.
We met outside San Domenico in Siena, where the stone felt cool under my hand and our guide, Paolo, waved us over with this easy smile. There were only six of us — I liked that right away. We piled into the minivan and rolled north, windows down just enough to catch that sharp morning air mixed with something herbal. Paolo pointed out the Chianti hills and I tried to imagine what it was like when these walls actually kept armies out.
Monteriggioni was smaller than I expected — almost toy-like, but real. The walls circle you completely, and there’s this hush inside, except for a couple of shopkeepers chatting over coffee. I lit a candle in the church because why not? It smelled faintly of wax and old stone. We wandered the alleys; Paolo told us about Dante mentioning this place in his Divine Comedy (which I pretended to have read more of). Then we headed for San Gimignano — those towers really do look like they’re daring you to guess their age.
The Via Francigena runs right through San Gimignano, which still bustles with travelers (and yes, some crowds). But there are moments: saffron in little glass jars catching sunlight in shop windows, the first taste of Vernaccia wine at lunch — crisp, almost floral. Lunch was at a family-run farm just outside town; everything on the table came from their fields or chickens. I tried to say “grazie” properly and got a gentle correction from Nonna herself. Still thinking about that saffron risotto.
Volterra felt different — quieter maybe, or heavier with history. We ducked into an alabaster workshop where two brothers worked side by side, hands white with dust as they shaped these impossibly smooth bowls. One let me touch a half-finished piece; it was cold and somehow soft at the same time. After that we had time to wander: Etruscan arches older than most countries, Roman stones underfoot, kids playing soccer near ruins like it’s nothing special. The light started to slant gold as we drove back toward Siena — tired in a good way, all of us quiet for once.
The tour lasts a full day, starting at 9:30am from Siena and returning in the evening.
Yes, a traditional Tuscan lunch is included at a small family-run farm near San Gimignano.
The group is limited to eight people for a more personal experience.
You can visit churches and museums during free time; entry fees are not included unless specified.
The tour includes transport by air-conditioned minivan but starts at San Domenico church in Siena; nearby parking is available if arriving by car.
Yes, there’s a stop at an artisanal alabaster workshop where you meet local craftsmen.
The tour is suitable for all fitness levels; specialized infant seats are available if needed.
Your day includes transport from Siena by minivan with an experienced local guide leading your small group through Monteriggioni’s fortress walls, San Gimignano’s medieval lanes (with time for shops), a homemade Tuscan lunch with wine at a family farm near San Gimignano, entry into an alabaster workshop in Volterra plus free time to explore before returning together in the evening.
Do you need help planning your next activity?