Small-Group Tuscany Vespa Tour with Lunch and Wine in Chianti
Ride through the Chianti hills, discover San Gimignano's skyline, and savour an authentic Tuscan lunch at a local winery.
This Tuscany Vespa tour from Florence takes small groups deep into the Chianti wine country, well beyond the city's crowded day-trip routes. Aboard a 50cc Vespa, you follow a local guide along winding country roads flanked by vineyards, olive groves, and cypress alleys. The day ends with a three-course Tuscan lunch and wine tasting at a family winery, making the experience as much about food culture as it is about the landscape.
Unlike tours that limit themselves to the hills just outside Florence, this itinerary pushes into the heart of the Chianti Classico zone near San Gimignano, one of Tuscany's best-preserved medieval towns. The route is chosen specifically for scenic value and low traffic, giving riders a genuine sense of the countryside rather than a motorway dash.
A test ride at the Chianti base ensures every participant feels comfortable on the scooter before the group sets off. The pace is unhurried, with multiple photo stops scheduled along the route so that the landscape can be appreciated without rushing from one checkpoint to the next.
The winery visit is hosted by the estate's owners, who walk guests through the vineyards and explain the production process before sitting down for the meal. Extra virgin olive oil produced on the property is included in the tasting, adding another layer of local flavour to the afternoon.
Tour Highlights
Ride your own 50cc Vespa through the scenic back roads of the Chianti region, a route reserved for this tour.
Pass through rolling hills covered in vineyards, ancient olive groves, and classic Tuscan cypress avenues.
Spot the iconic medieval towers of San Gimignano on the horizon and hear the history behind them from your local guide.
Enjoy a three-course authentic Tuscan lunch at a family-run winery, paired with estate wines and olive oil.
Stop at multiple photo points along the route to capture the timeless Tuscan countryside at its finest.
Travel in a small group with a knowledgeable local guide who shares stories about the region's history and winemaking traditions.
Complete a safety test drive at the Chianti base before departure, ensuring all riders feel confident on the road.
Itinerary
Arrive at the Florence office for check-in and document verification before the group departs for the Chianti region. The one-hour drive takes you through increasingly scenic Tuscan countryside as the guide introduces the day's programme and shares background on the region's history and wine culture.
Arrive at the tour's Chianti headquarters and meet the local ride leader. A test drive is conducted so that every participant can get comfortable with the scooter and review road safety procedures before the route begins.
Set off along quiet, winding roads through vineyards, cypress-lined lanes, and Tuscan farmsteads. Multiple photo stops allow the group to pause, take in the views, and capture the rolling landscape, including panoramic glimpses of San Gimignano's medieval towers on the horizon.
Pull up to a family-owned winery where the hosts lead a guided walk through the vineyards and explain the winemaking process. The group then sits down to a three-course Tuscan lunch accompanied by estate wine and extra virgin olive oil produced on the property.
Re-mount the Vespas for the final leg through the Chianti countryside before returning to the base. The group then boards the vehicle for the roughly 45-minute return journey to Florence, arriving back in the afternoon.
What's Included and Excluded
Included
- 50cc Vespa rental for the duration of the tour
- Helmet and safety equipment
- Local guide and ride leader throughout the day
- Three-course authentic Tuscan lunch at a winery
- Wine tasting with estate wines
- Extra virgin olive oil tasting
- Transport to and from Chianti (Florence transfer)
Not Included
- Gratuities for the guide (optional)
- Personal travel insurance
- Additional food or drinks beyond the included lunch
- Any items of a personal nature
Important Information
Ready to Ride Through Tuscany?
Secure your spot on this small-group Vespa tour and experience the Chianti countryside the way it was meant to be discovered — slowly, scenically, and with a glass of local wine in hand at the end of it.
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