Florence to Chianti: Wine Roads, San Gimignano & Lunch Tour

Chianti villages, Tuscan wine tasting and San Gimignano stroll

You’ll ride from Florence into classic Chianti villages with a local guide, taste Tuscan wines straight from family cellars, wander medieval San Gimignano on your own time, then share lunch at a working farmhouse. Expect laughter over bruschetta, stories from winemakers, and moments where Tuscany just feels close—you might not want to leave.

Step-by-step itinerary

Chianti villages and wine tasting tour

• Stop for photos in Montefioralle village
• Visit Tuscan winery and vineyard tour
• Taste Chianti Classico and Super Tuscany wines
• Explore medieval town of San Gimignano
• Enjoy light lunch with Tuscan appetizers
• Taste Tuscan wines and oils with dessert

The Experience

You step out of the minivan and right away it’s quiet—just the soft crunch of gravel underfoot and the smell of cypress. Our driver, Paolo, waved us into Montefioralle with a grin. He pointed at a stone wall covered in wild thyme and told us about the village’s old watchtower. I tried to picture medieval guards where now there’s just sunlight on old bricks. It’s funny how you can almost hear the past in these places, even if all you actually hear is someone’s dog barking down a side street.

The drive between villages felt like flipping through postcards—vineyards rolling by, olive trees everywhere. At the first winery, we met Francesca (she runs it with her brother). She handed me a glass of Chianti Classico and explained why their riserva tastes different—something about the soil, but honestly I was distracted by the smell: earthy and sharp at once. We tried salami that tasted smoky and bread dipped in oil so green it looked unreal. I asked about Super Tuscany wines and probably sounded clueless; Francesca just laughed and poured another splash.

San Gimignano surprised me—I’d seen photos but didn’t expect those towers to feel so close together or for the streets to be that steep. I wandered off for gelato (hazelnut, if you’re curious) while church bells echoed somewhere above. After that we drove just a few minutes to an old farmhouse for lunch. The kitchen smelled like rosemary and garlic when we walked in. There was bruschetta, pecorino cheese, more wine (I lost count), and cantuccini biscuits at the end—hard as rocks but perfect when dipped in sweet wine. Someone at our table tried speaking Italian; everyone laughed—including our host—and nobody minded getting it wrong.

I still think about that view from the vineyard—late afternoon light catching on rows of vines, everything golden and slow. It’s not fancy or staged; just real people making wine where their families always have. If you want a day trip from Florence that feels like you’re part of something local (even for a few hours), this is it.

What’s included

• Your day includes travel by air-conditioned minivan from Florence through Chianti villages with an English-speaking driver-guide.
• stops in Montefioralle and San Gimignano.
• guided tastings at two family-run wineries.
• a light Tuscan lunch at a historic farmhouse with regional appetizers and desserts.
• plus pickup from your accommodation if you book privately before returning to Florence in the evening.

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by ACCORD Italy Smart Tours & Experiences

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Top questions

How long is the day trip from Florence to Chianti?

The tour lasts approximately one day including travel time between Florence, Chianti villages, wineries, San Gimignano, and back.

Is hotel pickup included for this wine tour?

Yes, pickup at your accommodation is included if you select the private option—contact them with your address after booking.

What types of wines are tasted on this Chianti tour?

You’ll try several Tuscan wines: white sauvignon, rosé syrah blends, Chianti Classico vintage & riserva, plus Super Tuscany selections.

Does this tour include lunch?

Yes—a light lunch is served at a traditional farmhouse with Tuscan appetizers like bruschetta, cheeses, salami, biscuits and more wine.

Can children join this Florence to Chianti day trip?

Yes—infants and small children are welcome; prams/strollers fit in the vehicle and infant seats are available if needed.

How much free time do you get in San Gimignano?

You’ll have around 40 minutes to explore San Gimignano independently during the tour.

Are dietary requirements accommodated?

Please advise any specific dietary needs when booking so arrangements can be made for your meal during the tour.

Is public transportation available nearby for this tour?

Yes—public transportation options are available near meeting points if not using hotel pickup.