Tuscany Small-Group Afternoon Vespa Tour with Winery Stop and Tasting

Your experience

Ride a 2-hour small-group Vespa tour through the Tuscan countryside in the cooler afternoon, led by a professional tour leader.

Getting started

Meet your expert guide at the designated starting point and get introduced to your original Italian 50cc Vespa scooter with automatic transmission. After helmet fitting and a short orientation, you will complete an on-site driving test before departure so the team can verify real ability and confidence to drive safely. Once everyone is set, the small group of up to 6 Vespas rolls out into the Tuscan countryside.

What to expect

Tuscan countryside Vespa ride

This short afternoon Vespa tour follows quiet country roads through Tuscany, using the cooler part of the day to explore comfortably. The route runs through the scenic Chianti area and the hills around San Gimignano, with time for photo stops along the way.

Features

• Views unfold quickly as you ride past rolling vineyards, cypresses, olive groves, and Tuscan rural houses, with wide panoramas of the hills around San Gimignano that are ideal for capturing photos.

• The ride follows the scenic roads of Chianti, a region famous for its Tuscan wines, and passes medieval villages that give you a sense of the area’s rural history without long walking sections.

• Your format depends on the option selected at booking: choose a self-drive Vespa for guests aged 18+, a shared Vespa for driver and passenger, or a passenger-only ride on a Vespa if you prefer not to drive.

• Everything needed for the road is provided, including a 50cc Vespa scooter with automatic transmission, third-party insurance, helmet, and fuel, so you can focus on the experience instead of logistics.

• An engaging, fun, professional tour leader rides with the group, sets the pace, and manages safety, while the afternoon timing keeps the tour to about two hours and avoids the midday heat.

• Group size is limited to a small group of 6 Vespas, which keeps the convoy compact and makes it easier to navigate the countryside roads.

Local winery stop

Midway through the ride, the group pauses at a local winery set among vine fields and olive trees. This stop adds a relaxed tasting element to your afternoon on the road.

Features

• During the pause, you can experience a small tasting at the winery and sample Vernaccia white during the dedicated Vernaccia white tasting, a regional pour closely associated with nearby San Gimignano.

• The setting among vineyards and olive groves gives you time off the scooter to look back over the surrounding Chianti landscape and take more photos before returning to the Vespas.

• This stop is included as part of the afternoon Vespa tour in the Tuscan countryside, so there is no need to arrange separate visits or tastings.

Wrapping up

After the winery stop, you ride back along countryside roads to the original starting point where the tour concludes, and Vespas and helmets are returned; gratuities and any hotel pickup from accommodation or Poggibonsi train station are not included in the tour price.