San Gimignano Vespa Tour: Chianti Hills, Lunch & Wine
You ride your own scooter on roads built for photographs, not traffic.
A small-group Vespa tour from San Gimignano takes you through the Chianti region on a 50cc automatic scooter, with a professional guide leading no more than seven riders at a time. The route winds through rolling vineyards, olive groves and rural Tuscan villages, stopping for photos and stories along the way. Lunch and wine tasting happen at a local winery mid-tour. A driving test before departure confirms you're confident on the bike, and if you're not, you can ride double with a partner or as a passenger instead.
Step-by-step itinerary
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 for tour and Tuscan meal
- Continue scenic Vespa drive with guide
- Return to starting point and final vehicle check
The experience
The morning starts at the Tuscany on Wheels office in Barberino Tavarnelle, about 12 kilometers from San Gimignano. You'll park your car free or arrange a paid pickup in advance, then meet the guide and run through a safety briefing and a short driving test on the Vespa itself. This is how the team makes sure you're ready to ride. The bike is a Vespa Primavera 50cc or Zip with automatic transmission, which means no gear shifting. It weighs 88 kilograms and has a top speed of 48 kilometers per hour on flat roads, slower on hills. If the test shows you're not comfortable, you can ride as a passenger with a partner or in a tuk tuk instead, and the tour continues the same way.
Once the group is ready, you head out onto the panoramic roads of Tuscany. The route takes you through the Chianti hills where the landscape is vineyards, cypress trees and scattered rural houses: the kind of view that stops people mid-ride to pull out a camera. The guide stops a few times along the way for photos and to share stories about the area, so you're not just moving through it. The roads are off-the-beaten-track, which is why the small group size matters: seven Vespas together draw attention without overwhelming the places you pass through.
Midway through, you arrive at a local winery where the owners walk you around the property before serving a traditional Tuscan lunch with three wines and extra virgin olive oil to taste. This is the centerpiece of the day, not a quick stop but a proper meal and tasting experience. After lunch, you ride again for the final stretch back to the office, with more stories from the guide along the way. The whole outing, including the pre-tour procedures and a final vehicle check when you return, takes about six hours.
What’s included
- A 50cc Vespa Primavera or Zip with automatic transmission, helmet and fuel.
- a professional tour leader who speaks English or Italian.
- third-party insurance.
- orientation and a driving test before departure.
- stops for photos and guide stories through the Chianti region.
- a traditional Tuscan lunch with three wines and extra virgin olive oil tasting at a local winery.
- a final vehicle check when you return.
Options for this experience
4 optionsInformation
Lasts 6h, runs Monday to Friday at 10:00 and 10:45, from € 139 per person, with a live guide in English and Italian, in groups of up to 14 and with free cancellation up to 24 h before.
Prices and times updated today
Operated by Italy on a Budget tours
Is this one for you?Choose the self-drive option if you want to feel the roads yourself and have ridden scooters or motorcycles before. Book as a passenger if you'd rather enjoy the route without handling the bike, or pick the tuk tuk if you want to skip two wheels altogether. The small group size, seven Vespas maximum, means the roads stay quiet and the stops feel unhurried, which is what makes a half-day in Chianti feel like a full escape instead of a tick on a list.
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Top questions
What languages is the tour guided in?
Live guide in English and Italian.
What happens if it rains?
It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.
Do I need previous scooter experience to book this tour?
Yes, previous scooter or motorcycle driving experience is required. The team conducts a driving test before departure to confirm you're confident on a Vespa. If you're not comfortable after the test, you can ride double with a partner or as a passenger instead, and the tour price remains the same.
What's included in the winery stop?
The winery visit includes a tour of the property led by the owners, a traditional Tuscan lunch, and a tasting of three wines plus extra virgin olive oil.
Can I ride as a passenger if I don't want to drive?
Yes. You can choose to ride as a passenger on a Vespa with a partner, or book the tuk tuk option if you prefer not to ride a scooter at all.
What documents do I need to bring?
You must bring a valid driver's license that is recognized in Italy. Riders must be at least 18 years old. Passengers must be at least 15.
Where do I meet the group?
You meet at the Tuscany on Wheels office in Barberino Tavarnelle, about 12 kilometers from San Gimignano, near the Poggibonsi Nord exit of the Firenze-Siena highway. Free parking is available at the office, or you can request a paid pickup in advance.
San Gimignano Vespa Tour: Chianti Hills, Lunch & Wine
6h · EN · IT
from € 139 per person
≈ US$ 159 in your currency