Tuscany: Vespa Tour with Chianti Winery Lunch & Wine Tasting

Summary

Vespa rides winding past vineyards and olive groves in Chianti

You’ll ride your own Vespa through winding Tuscan roads with a local guide, pausing for views across Chianti’s vineyards before settling into a family-run winery for lunch and wine tasting. Expect laughter over shared plates, olive oil tastings straight from the source, and small moments—like sunlight flickering through cypress—that stay with you long after you’ve returned to Florence.

What’s the experience like?

We climbed into the minivan just off Via dei Pandolfini, still shaking off Florence’s morning noise. It only took half an hour before we were standing in the middle of quiet green, the kind you see in postcards but never think you’ll actually touch. The air smelled like cut grass and something sweeter—maybe wildflowers? Our guide, Paolo, handed out helmets and grinned at my nervous grip on the Vespa handles. “Don’t worry,” he said, “everyone wobbles at first.” He was right. I did wobble. But after the lesson, I was zipping along behind him, hair whipping under my helmet and sun flickering through cypress trees.

The roads twisted and dipped through those Tuscan hills—sometimes so narrow that I wondered what would happen if a tractor came around the bend (it didn’t). We stopped more than once just to stare out at lines of grapevines rolling away into haze. Someone tried to take a selfie with their helmet still on and almost dropped their phone; everyone laughed, even Paolo. There was this moment where all you could hear was cicadas and our engines cooling down in the shade. I didn’t expect to feel so far from everything else.

Lunch happened at a family winery tucked behind olive trees—nothing fancy, just big wooden tables and food that tasted like someone’s grandmother had made it. There was fresh bread dunked in peppery olive oil, pasta with tomatoes so sweet they almost felt wrong, glasses of Chianti poured by the owner herself (I tried to pronounce her name—she smiled politely). The tour of the cantina felt easygoing; barrels everywhere, cool stone underfoot, smells of fermenting grapes mixing with dust. After that meal—and maybe one too many sips—I felt sun-heavy and happy in a way I can’t quite explain.

I keep thinking about that stretch of road where everything went quiet except for wind and distant church bells. If you’re looking for a day trip from Florence that feels like stepping sideways out of time—well, this Tuscany Vespa tour is probably it.

Step-by-step itinerary

Day 1 — Vespa tour and lunch in Chianti

• Depart Florence at 10 am
• Arrive at private Chianti winery
• Take Vespa driving lesson
• Ride Vespa through countryside
• Stop for pictures along route
• Visit family-owned winery cantina
• Enjoy traditional Tuscan lunch with wine
• Return to Florence by van

Top questions

Is pickup from Florence included in the Tuscany Vespa tour?

Yes, transport by minivan from Florence to the starting point in Chianti is included.

Do I need experience riding a Vespa for this tour?

No experience needed—a lesson is provided at the start so beginners can learn safely.

Is lunch included during the Vespa wine tour?

Yes, a traditional Tuscan lunch is included at a family-run winery along with wine tasting.

Can vegetarians be accommodated on this tour?

Yes, vegetarian options are available if advised at booking.

What do I need to bring for the Tuscany Vespa tour?

You must bring a valid driver’s license; everything else is provided including helmets.

How long does it take to reach the countryside from Florence?

The drive by minivan takes about 30 minutes from central Florence to Chianti.

Is there an age requirement for driving the Vespa?

The minimum age is 18 years; under 18s can join as passengers only.

Can I buy wine or olive oil during the visit?

Yes, there’s an option to purchase wine and olive oil directly from the winery.

What’s included

Your day includes pickup by minivan from Florence to Chianti, orientation and safety briefing before riding your own automatic Vespa (with all gear provided), guidance from a local expert throughout winding countryside roads, entry to a private family winery with tours of both vineyard and cantina, plus a traditional Tuscan lunch featuring local wines and extra virgin olive oil tasting before returning comfortably back to Florence in the afternoon.