Florence to Siena & Chianti: Private Wine Tour with Pickup

5.00

(43 reviews)

What’s the experience like?

Hands gripping the edge of my seat, I watched the cypress trees flick past as our driver—Marco, who greeted us like old friends—navigated those winding roads out of Florence. He asked if we’d ever tried real Chianti before, and when I hesitated, he just grinned and said, “You will today.” The air outside smelled faintly of earth and something sweet—maybe wildflowers? Greve in Chianti was our first stop, and honestly, I didn’t expect the square to feel so lived-in. Locals chatting over espresso, a butcher shop window full of things I couldn’t name (Marco insisted we try finocchiona; I still can’t pronounce it right).

The drive through Chianti’s hills was quieter than I thought it’d be. Just us, vineyards rolling out on both sides, sunlight flickering through olive branches. Marco pointed out Panzano’s church tower in the distance—he said it’s halfway between Florence and Siena, which made me laugh because it felt like we were in the middle of nowhere (in a good way). At the winery, the cellars were cool and smelled like old wood and grapes. Our guide there explained how they make Chianti Classico—she even let us taste olive oil straight from the estate. It was peppery and green; totally different from what I buy at home.

If you’re into food (who isn’t?), there’s this family-run spot nearby called La Locanda di Pietracupa. We almost skipped lunch but ended up sharing pasta with wild boar ragù that I’m still thinking about. Siena came after—a quick walk from where Marco dropped us off by the cathedral. The marble stripes on the Duomo looked unreal in the late afternoon light. Piazza del Campo was busier than I expected; kids chasing pigeons, someone strumming a guitar off to one side. We wandered without much of a plan—sometimes that’s better anyway.

The drive back to Florence was quiet again. Maybe it was all that wine or maybe just tired in a good way. There’s something about seeing Tuscany this way—with someone local showing you around—that makes everything feel less like a checklist and more like you’re actually part of it for a day.