Florence Walking Tour & Wine Windows Option with Local Tastings

4.64

(245 reviews)

What’s the experience like?

We met up in Piazza della Repubblica—right under that old carousel, which was already spinning even though it was barely morning. Our guide, Chiara, waved us over with this big smile and a blue scarf (she said it helps people spot her). She started talking about how this square used to be the Roman forum and I kept glancing up at those faded arches thinking about how many feet have crossed here. There was this faint smell of coffee drifting over from somewhere—maybe Gilli?—and honestly I almost wandered off after it. But Chiara had us moving, weaving through narrow lanes where the stones felt slick under my shoes from last night’s rain.

I didn’t expect to laugh so much on a Florence walking tour. At San Lorenzo, Chiara pointed out the Medici Riccardi Palace and told us how Cosimo de’ Medici basically ran the city from there—she called him “the original influencer,” which cracked everyone up. There were these little moments: an old man shouting buongiorno to a shopkeeper across Via Calzaiuoli; the way sunlight caught on the gold leaf above Orsanmichele’s doors; a street musician plucking something that sounded like Vivaldi but maybe wasn’t. The keyword “Florence walking tour” doesn’t really capture how alive it all feels when you’re right there.

If you pick the wine windows option (which I did because why not), there’s this part where you get handed a glass of red through an actual buchetta del vino—a tiny stone window in someone’s wall. It’s weirdly intimate, like you’re sharing a secret with the city itself. The wine tasted earthy and bright at once; I tried to ask for another in Italian but probably butchered it because the woman inside just laughed and handed me some cheese instead. That little exchange stuck with me more than anything else we saw—funny how travel works sometimes.

By the time we ended near Via Cavour, my feet were tired but my head was buzzing with stories—Medici plots, saints in hidden chapels, even that pig statue at Mercato Nuovo (Chiara says rubbing its nose brings luck; I did it twice just in case). I still think about that first sip of wine through cold stone, and how Florence feels less like a museum and more like a living thing when you walk it with someone who knows every twist and echo.