Florence to Siena & San Gimignano: Chianti Winery Dinner Tour

Summary

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.

What’s the experience like?

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.

Step-by-step itinerary

Day 1 — Tuscany towns and winery dinner

• 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

Top questions

How long is the day trip from Florence to Siena & San Gimignano?

The tour lasts an afternoon into evening, returning to Florence after dinner at the winery.

Is transportation included for this Florence day trip?

Yes, round-trip transport from Florence is provided by luxury minivan or minibus.

Do I get free time in San Gimignano?

Yes, you’ll have time to explore San Gimignano on your own before heading to dinner.

Is dinner included at the Chianti winery?

A typical Tuscan dinner with wine tasting is included at a boutique winery in Chianti.

Are guided tours part of this experience?

You’ll have a guided walking tour in Siena; other stops are self-guided or relaxed.

Can infants join this Tuscany tour?

Infants are welcome; strollers and specialized infant seats are available if needed.

Does this tour run if it rains?

The tour operates regardless of weather conditions.

What languages does the guide speak?

The main tour leader speaks English throughout the journey.

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.