Chianti & San Gimignano: Wineries Tour, Tuscan Lunch & Gelato

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Free cancellationTravelers' pick

1/46

Duration8h

GroupUp to 16

LanguagesEN · IT +1

Mobile ticketAccepted

Chianti wine tasting lunch plus San Gimignano stroll and Florence view

You’ll wander Chianti’s vineyards with a local guide, taste fresh olive oil and wines straight from the source, explore San Gimignano’s medieval charm (and world-famous gelato), then share an easygoing Tuscan lunch at another winery before catching sunset views over Florence. Expect laughter, good food, and small surprises along the way.

Step-by-step itinerary

Chianti wineries, San Gimignano, Florence

Visit first Chianti winery
Tour medieval San Gimignano village
Try world champion Dondoli gelato
Visit second winery for lunch and tasting
Stop at Piazzale Michelangelo viewpoint

The Experience

“You’re not supposed to swirl it like that!” Marco grinned at me as I nearly sloshed Chianti onto the cellar floor. The first winery was already humming with that peppery smell of barrels and earth — honestly, I still get flashes of it when I open a bottle at home. Our guide (she grew up nearby, knew every hill) walked us through the olive oil secrets too. I didn’t expect to care about olive oil, but there’s something about dipping bread while sunlight flickers through those old stone windows — you just slow down. We tasted three wines and I bought a bottle for way less than what I’d pay back in Florence.

San Gimignano hit me differently. Maybe it was the way the towers slice up the sky or just how everyone seemed to be moving slow, like they had all day. We wandered narrow lanes that smelled faintly of leather and espresso — I tried to order gelato in Italian (“stracciatella,” which is harder to say than you’d think). Dondoli himself wasn’t there but his staff handed over this cold cup that somehow tasted both new and familiar. My friend kept laughing at my face after that first bite — apparently I looked shocked? Anyway, you get free time here; we just sat on a low wall watching people drift by.

The second winery felt more relaxed — maybe because we’d already done our “serious” tasting. Lunch was simple: bread with tomatoes, pecorino cheese, something called pappa al pomodoro (I asked for seconds). The wine class part was easygoing; nobody made you feel dumb for not knowing tannins from whatever else. On the drive back toward Florence, we stopped at Piazzale Michelangelo. The city below looked almost unreal in late afternoon light — someone nearby played guitar softly, which sounds fake but really happened. It was one of those moments where you don’t want to take a photo because it won’t catch what you’re actually feeling.

What’s included

Your day includes comfortable minivan transport from Florence with live commentary on board, guided visits to two Chianti wineries (with tastings), a traditional Tuscan light lunch paired with local wines, a stroll through San Gimignano (plus time for champion gelato), and a scenic stop at Piazzale Michelangelo before heading back in the evening.

Good to know

Easy physical levelStroller friendlyInfant seats available

Operated by Chianti Wine Tour