Italy » Tuscany » Florence | 🏛 Florence Wine Tour · Florence Food Tour

Florence to Siena & San Gimignano: Chianti Winery Dinner Tour

★★★★★★★★★★ 4.70 (312 reviews) 82% rated it 5 stars

Free cancellationExcellent quality

1/32

Duration9h–12h

GroupUp to 20

LanguagesEN

Mobile ticketAccepted

Wander Siena’s Contrade, climb San Gimignano towers, dine in Chianti vineyards

You’ll start in Florence and travel through Tuscany with a local guide, walking Siena’s medieval streets and tasting fresh pastries before exploring San Gimignano at your own pace. As evening falls, enjoy a traditional Tuscan dinner with wine at a boutique Chianti winery—those sunset views linger long after you return.

9h–12h

Step-by-step itinerary

Depart from Florence meeting point
Guided walking tour of Siena
Free time in San Gimignano
Dinner and wine tasting at Chianti winery
Return to Florence meeting point

The Experience

We met our guide near Florence’s center—she waved us over with this big smile, like she’d been waiting for friends. The drive out toward Siena was quieter than I expected; just the soft hum of the minivan and those green hills rolling past. In Siena, our guide (Giulia? Julia? I’m still not sure how to say it right) led us through the Contrade. She pointed out these flags and little fountains I would’ve missed—apparently each neighborhood has its own animal mascot. There was a bakery smell drifting from some side street, sweet and warm. Someone handed out tiny pastries as a “surprise tasting”—I still don’t know what they were called but they were gone fast.

San Gimignano came next. It’s one of those places you see in postcards but it feels different when you’re actually there—stone towers against the sky, laundry flapping from windows. We had free time so I wandered off and bought gelato from a guy who insisted his family invented the recipe (maybe true, maybe not). I tried to peek inside the Basilica of Santa Maria Assunta but there was a wedding going on—everyone outside seemed to be related, hugging and laughing in bursts. The air smelled like old stone and flowers.

The sun started dropping as we drove into Chianti country. The winery sat on a hill—the kind of place where you can see rows of vines stretching forever. Dinner was simple: bread with olive oil that tasted peppery, pasta with wild boar ragù (I hesitated but ended up loving it), and local wine poured by someone who kept calling us “amici.” Our group lingered longer than planned; nobody really wanted to leave that table or that view. On the ride back to Florence, everyone got quiet—maybe tired or just full in every sense. I keep thinking about that light over the vineyards as we left.

What’s included

Your day includes round-trip transportation from Florence by luxury Mercedes minivan with free WiFi onboard, an English-speaking guide for Siena’s walking tour plus surprise tasting there, free time in San Gimignano (with entry possible to sites like Basilica di Santa Maria Assunta), and finally a Tuscan dinner with wine tasting at a boutique winery before returning late evening.

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by Towns of Italy