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Tuscany: Chianti Wine Tour & San Gimignano with 2 Tastings

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Free cancellationExcellent quality

1/13

Duration6h

GroupUp to 16

LanguagesEN

Mobile ticketAccepted

Chianti wine tasting day trip from San Gimignano with local stops

You’ll taste up to nine Tuscan wines at two family-run wineries in Chianti, sample truffle oil and aged balsamic vinegar, and wander medieval San Gimignano’s streets with time for gelato or quiet moments by the basilica. With roundtrip transport and an English-speaking guide handling all the details, you can just relax into the rhythm of Tuscany—and maybe discover your new favorite wine along the way.

Step-by-step itinerary

Start from Tuscany on Wheels or San Gimignano
Visit first winery near Florence
Taste 5 wines and balsamic vinegar
Visit second winery near San Gimignano
Tour vineyards and cellars
Taste 3 wines and learn pairings
Stroll in San Gimignano medieval town
End tour at Tuscany on Wheels or San Gimignano

The Experience

I didn’t expect the air outside San Gimignano to smell like wild herbs—kind of sharp and sweet at the same time. Our guide, Francesca, waved us into the van with a grin that made me feel like we’d known her for ages. It was one of those mornings where the light is soft but you can already tell it’s going to be warm later. I kept staring out the window as we drove past olive trees and those weirdly perfect rows of vines. Honestly, I thought I knew what “Tuscany” looked like from photos, but it’s different when you’re actually there, dust on your shoes and all.

The first winery was run by a family who’ve apparently been making Chianti Classico since before my country even existed. We tried five wines—my favorite was this Vernaccia white that tasted almost salty? Or maybe that was just me. There was also a balsamic vinegar older than me (thick as syrup), plus truffle oil that made everyone go quiet for a second. Francesca taught us how to swirl and sniff properly; mine still smelled mostly like “wine,” but I pretended otherwise. The winemaker told stories about his grandfather hiding barrels during the war—he shrugged like it wasn’t a big deal, but you could tell it was.

The second stop overlooked San Gimignano’s towers—those stone fingers poking at the sky. The sun hit everything gold and I had to squint. The winemaker there showed us around the cellar; she let me touch one of the barrels (cool and a bit sticky). We tasted three more wines, including their D.O.C.G. Vernaccia and a rosé that surprised me—never really liked rosé before. Someone asked about shipping bottles home and she laughed, said they send wine everywhere except Antarctica (I wonder if she was joking). Afterward we got free time in San Gimignano itself; I wandered off for gelato and ended up sitting on a step near Basilica di Santa Maria Assunta just watching people go by.

I still think about that view over the vineyards—the kind where you want to take a photo but know it won’t come out right anyway. On the drive back, Francesca played some old Italian songs and everyone got quiet in that sleepy, happy way after good food and wine. If you’re looking for a day trip from San Gimignano or Florence where you don’t have to think about driving or planning anything complicated… well, this is probably it.

What’s included

Your day includes roundtrip transportation from either Tuscany on Wheels’ office or central San Gimignano (with free parking if needed), guided visits at two local wineries with up to nine Tuscan wines to taste—including Chianti Classico and Vernaccia—as well as samples of truffle oil and aged balsamic vinegar paired with snacks. You’ll also get free time in medieval San Gimignano before heading back in the afternoon alongside your English-speaking guide.

Good to know

Easy physical levelPublic transport nearby

Operated by Italy on a Budget tours