Chianti & San Gimignano: Wine Tour, Medieval Towns & Tuscan Lunch

4.96

(121 reviews)

What’s the experience like?

The first thing I remember is the way the morning sun hit the stone walls as we left Florence—golden, like someone had painted it on just for us. Our guide, Marco, had this habit of humming quietly when he drove, which made me feel oddly calm even though I’d barely slept the night before. We wound through those Tuscan hills (they really do look like postcards), and I kept catching whiffs of wild herbs when we rolled down the windows—rosemary maybe? Or something sharper. The air felt different out there. Cleaner, but also a bit earthy.

At the first winery in Chianti, a woman named Lucia showed us around. She spoke with her hands as much as her voice—at one point she handed me a grape that was still warm from the sun. Tasted sweeter than I expected. The cellar was cool and smelled like old wood and something deeper I couldn’t place; maybe that’s what years of wine do to a place. We tried three different Chianti wines (I liked the second best), plus olive oil that actually tasted green if that makes sense. Lucia laughed when I asked if people here ever get tired of wine—she just shook her head.

San Gimignano looked unreal at first, all those towers poking up against the sky like some medieval skyline. We had free time to wander—I got lost twice but didn’t really mind because every corner had something: laundry flapping out a window, an old man arguing with his granddaughter about gelato flavors (I think). I finally found Dondoli’s gelateria and ordered whatever everyone else was having. It melted faster than I could eat it but tasted like summer itself.

The lunch at our second winery felt almost like visiting someone’s home—big wooden tables, mismatched chairs, laughter bouncing off stone walls. Homemade pasta with a sauce that clung to every bite, more wine (of course), cheeses and bread that disappeared too fast. There was this moment where everything went quiet except for birds outside and forks scraping plates—I still think about that silence sometimes.