San Gimignano: Tuscany Vespa Tour, Lunch & Wine Tasting

Summary

Vespa ride through chianti hills with tuscan lunch and wine

You’ll zip through Tuscany’s Chianti hills on your own Vespa (or as a passenger), guided by locals who share stories along winding roads lined with cypress trees. Taste three local wines and fresh olive oil during lunch at a family-run winery—expect laughter over mispronounced Italian words and time to soak up those vineyard views before heading home.

What’s the experience like?

The first thing I noticed was the Vespa’s engine—a soft putter, almost shy at first, echoing off the stone walls near San Gimignano. Our guide, Matteo, handed me a helmet with a grin and said something about “la dolce vita.” I tried not to look nervous during the driving test (I probably failed at hiding it), but he just nodded and told me I’d get used to the curves. The air smelled faintly of wild herbs and gasoline—oddly comforting. After we all passed the test (one guy nearly toppled over but laughed it off), we set off into those rolling Chianti hills.

There’s this stretch where cypress trees line both sides of the road like they’re keeping secrets. Matteo slowed down so we could catch up, pointing out old farmhouses tucked between vineyards. At one stop, he told us about his grandmother making olive oil by hand—his hands moved in slow circles as he spoke, like he was kneading dough. I snapped a photo that didn’t do justice to how green everything looked. The main keyword here is Tuscany Vespa tour, but honestly, it felt more like being part of someone’s everyday life than a tour.

Lunch was at a small winery—family-run, with big wooden tables that creaked when you sat down. The owner poured us three different wines and let us dip bread into fresh olive oil (peppery and grassy—I had no idea olive oil could taste like that). Someone tried to pronounce “bruschetta” properly; Matteo chuckled and corrected us gently. We lingered longer than planned, swapping stories with the owners while sunlight drifted across the table.

The ride back was quieter—maybe everyone was full or just soaking it all in. My hands smelled faintly of rosemary from touching some wild bushes along the way. When we finally parked our Vespas back at the office near Barberino Tavarnelle, I felt oddly proud for not tipping over once. I still think about that view from the hilltop outside San Gimignano—somehow bigger than any photo could show.

Step-by-step itinerary

Day 1 — Vespa tour with lunch and wine tasting

• Meet team at Tuscany on Wheels office
• Complete pre departure procedures and driving test
• Ride through Tuscany and Chianti hills
• Stop for photos and listen to guide stories
• Visit local winery and tour property
• Enjoy Tuscan meal with wine and olive oil tasting
• Continue scenic drive on Vespa
• Return to starting point and final vehicle check

Top questions

Do I need previous experience to join the Tuscany Vespa tour?

Yes, previous scooter or motorcycle experience is required. A driving test is done before departure for safety.

Where does the Vespa tour start near San Gimignano?

The tour starts at the Tuscany on Wheels office in Barberino Tavarnelle, about 12km from San Gimignano.

Is pickup included for this day trip from San Gimignano?

Pickup can be requested in advance for an extra fee; otherwise, free parking is available at the meeting point.

What’s included in the Tuscan lunch and wine tasting?

You’ll have an authentic Tuscan meal at a local winery with three wines and extra virgin olive oil to taste.

How long does the whole Vespa tour take?

The total experience takes around 6 hours including check-in procedures; riding time is about 4 hours.

Can I ride as a passenger if I’m not confident driving?

If you don’t pass the driving test or prefer not to drive, you can ride double with your partner if possible.

What documents do I need for this tour?

You need a valid driver’s license accepted in Italy and a credit card for vehicle guarantee (no prepaid cards).

Is this Tuscany Vespa tour suitable for beginners?

No; some prior experience is necessary since there are safety checks before joining the group ride.

What’s included

Your day includes use of a classic 50cc Vespa scooter (with helmet and fuel), guidance from an engaging local leader through scenic Chianti routes near San Gimignano, several stops for photos and stories, third-party insurance coverage, an orientation plus driving test before departure, plus a traditional Tuscan lunch with three local wines and fresh olive oil tasting at a family-run winery—and optional pickup if arranged ahead of time.