Tuscany Private Day Tour to Val D'Orcia & Wineries

4.83

(24 reviews)

What’s the experience like?

Someone’s handing me a tiny glass — ruby red, smells like cherries and something earthier. Our guide, Paolo, grins and tells us this is what Montepulciano tastes like when it rains in spring. I’m not sure what that means but after the first sip, I sort of get it. We’d just wandered up the cobbled streets, past a cat sleeping on a windowsill (it didn’t even flinch when I tried to say “buongiorno”). The view from up there — green hills rolling out forever, cypress trees lined up like they’re posing for a painting. It’s hard not to stare.

We pile back into the van — private tour means no waiting for stragglers, which I appreciate more than I thought I would. Pienza comes next. The air smells faintly of cheese (pecorino, Paolo says, and then laughs when I try to pronounce it). The squares feel almost too perfect, but there’s this old man feeding pigeons who waves at us like he knows we’re not from here. There’s something about the way the light hits those Renaissance buildings — soft edges everywhere.

I keep thinking about how quiet Val D'Orcia feels once you leave the main road. At one point we stopped just because someone wanted a photo — nobody rushed us. The hills were patchy with wildflowers and olive trees; you could hear bees if you listened. Montalcino was our last stop: medieval walls, a castle that looks straight out of some storybook (Paolo told us a legend about ghosts but honestly I was more interested in the Brunello wine). We sat outside for a while before heading back — tired in that good way you get after walking all day, shoes dusty and head full of new things. Still think about that view sometimes.