Florence to Chianti & San Gimignano: Small Group Wine Day Trip

4.88

(189 reviews)

What’s the experience like?

I didn’t expect the view from Piazzale Michelangelo to hit me like that — Florence just sprawled out under the morning haze, all those pale rooftops and that dome. Our guide, Luca, waved us over for photos but I was still sort of stuck just staring. There was this faint smell of coffee drifting up from somewhere below; I remember thinking how everyone else in the city was probably just starting their day while we were already off chasing wine in Chianti.

San Gimignano came next, all stone towers and narrow alleys. It’s busy but not in a bad way — schoolkids laughing, an old man with a floppy hat selling postcards. We tried the gelato (apparently world-famous) and yeah, it’s good, though I managed to drip some on my shirt. The town feels ancient but alive at the same time. I kept craning my neck at the towers, imagining what it must’ve been like centuries ago with rival families trying to outdo each other.

The real highlight for me was lunch at this farmhouse in the heart of Chianti. The table was set under these low wooden beams and there was a breeze carrying that grassy-warm smell you only get in Tuscany. We tasted several Chianti wines — honestly, I lost count after four — and dipped bread into peppery olive oil straight from their grove. Someone asked about the difference between Chianti Classico and Riserva and our host explained it with so much pride you could tell it wasn’t just business for them.

Last stop: another family-run winery near Florence. By then we were all a bit giggly (maybe it was the Prosecco they popped open for us in the van). The sun started slanting low through the vineyards — golden light everywhere. I still think about that view sometimes when I’m back home pouring myself a glass of red. So yeah, if you’re looking for a day trip from Florence that’s more than just ticking boxes, this one sticks with you.