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

Summary

Chianti wine tastings, San Gimignano towers and homemade pasta in the hills

You’ll wind through Tuscany’s hills from Florence to Chianti for tastings at two family-run wineries, stroll San Gimignano’s medieval lanes (and try world-famous gelato), then sit down for a real Tuscan lunch with local wines—all in a small group led by a local guide who knows every shortcut and story.

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.

Step-by-step itinerary

Day 1 — Chianti wineries and medieval villages

• Visit first winery farm
• Guided wine, olive oil, food tastings
• Tour medieval Manhattan sites and towers
• Free time for shopping and gelato
• Enjoy authentic Tuscan lunch at second winery
• More wine tasting at second winery
• Visit Piazzale Michelangelo for city view

Top questions

How many wineries do you visit on this Chianti wine tour?

You visit two wineries in the Chianti area for guided tours and tastings.

Is lunch included during the day trip from Florence?

Yes, an authentic Tuscan lunch with wine tasting is included at the second winery farm.

Does this tour include time in San Gimignano?

Yes, you’ll have guided time plus free time to explore San Gimignano’s medieval center.

What kind of transportation is used on this tour?

The tour uses an air-conditioned minivan for up to 8 people per group.

Are children or infants allowed on this Chianti day trip?

Yes, children and infants are welcome; infant seats are available if needed.

Is there hotel pickup included in Florence?

No hotel pickup is mentioned; departure is from Florence city center locations.

Do you get to taste olive oil as well as wine?

Yes, tastings include local olive oil along with wines and cheeses.

How long do you spend in San Gimignano?

You have enough free time to explore and enjoy gelato after a guided walk of key sites.

What’s included

Your day includes travel by comfortable minivan through Tuscany’s countryside from Florence, visits to two favorite wineries for guided cellar tours and tastings of Chianti wines and olive oil, plenty of time exploring San Gimignano (with its famous gelato stop), plus a full Tuscan lunch with more local wine before heading back—with your licensed guide handling all the details so you can just enjoy it all.