Florence to Tuscany: Vespa Tour, Medieval Town & Wine Lunch

Summary

Vespa through rolling vineyards then taste Chianti in a hilltop town

You’ll ride a Vespa through Tuscany’s countryside from Florence with a local guide leading the way, pause for gelato in a medieval hilltop village, and share lunch with Chianti wine at a family-run winery. Expect laughter over wobbly starts and unforgettable views—this day trip is all about soaking up real Tuscan moments.

What’s the experience like?

The first thing I remember is the sound — those little Vespas buzzing as we left Florence behind, morning light flickering through olive trees. Our guide Marco handed me my helmet and grinned, “Don’t worry, everyone wobbles at first.” He was right. I did wobble. But after a few minutes, it felt like flying (well, sort of). The air smelled faintly of wild herbs and dust — you know that dry summer scent? We zipped past vineyards with old stone walls and sunflowers nodding along the roadside. I caught myself laughing for no reason at all.

We stopped in this medieval town perched up on a hill — San Gimignano, I think? The towers looked like chess pieces. Marco led us through narrow lanes where laundry flapped from windows and a cat stretched in the shade. He pointed out some old well where people used to gather water (“before espresso machines,” he joked). There was time to wander off; I found myself in front of Gelateria Dondoli, which apparently wins awards every year. Pistachio gelato, so cold it made my teeth hurt but worth it. Some locals chatted nearby in that sing-song Italian — wish I could’ve understood more.

Lunch happened at a winery outside town. Long table under vines, plates of bread with olive oil, salami, cheese — simple but somehow perfect after riding all morning. They poured us Chianti wines (I lost track after the second glass), and someone explained how the soil here gives the grapes their flavor. Sunlight kept shifting across the tablecloths. It’s funny how quickly strangers become friends when you’re passing bottles around and swapping stories about almost crashing your Vespa into a cypress tree (just me?).

I didn’t expect to feel so free or to care so little about looking silly in front of strangers. Maybe that’s what Tuscany does to you — or maybe it was just the wine talking by then. Either way, I still think about that view from the hilltop road as we headed back toward Florence, wind tugging at my jacket sleeves and everything golden for a minute longer than seemed possible.

Step-by-step itinerary

Day 1 — Vespa ride and wine tasting tour

• Ride Vespas in countryside
• Visit medieval Tuscan village
• Free time in village streets
• Try gelato at Dondoli shop
• Enjoy Tuscan light lunch
• Guided Chianti wine tasting

Top questions

Is hotel pickup included on this Tuscany Vespa tour?

No, but public transportation options are available nearby for easy access to the meeting point.

Do I need experience driving a Vespa for this day trip?

No prior experience is required—just bring your original driver’s license and be over 18 years old.

Is lunch included during the Vespa tour from Florence?

Yes, a typical Tuscan light lunch with wine pairing at a local winery is included.

How many people are on each Tuscany Vespa tour?

The small group size is up to 8 people per tour.

Can children join this Tuscany day trip by Vespa?

The tour is kid- and family-friendly; specialized infant seats are available if needed.

What medieval town do we visit during this tour?

You’ll visit one of Tuscany’s most charming medieval towns—often San Gimignano—with free time to explore.

Are entry fees or taxes included in this Vespa wine tour?

Yes—all fees and taxes are covered as part of your booking.

What’s included

Your day includes riding your own Vespa moped with helmet provided, guidance from a licensed local guide and driver throughout Tuscany’s countryside, stops in one of its most charming medieval towns (with time for world-champion gelato if you want), plus all fees and taxes covered—and wraps up with a typical Tuscan light lunch paired with local Chianti wines before returning to Florence.