Day Trips

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

Take the handlebars of a 50cc automatic Vespa and glide between vineyards, olive groves, and San Gimignano hills on an afternoon countryside ride.

Meet your expert guide for orientation and a driving test, then roll out together in a line along country roads outside San Gimignano.

Ride a loop along Tuscan backroads between small villages, with helmet, fuel, and third-party insurance already taken care of for you.

Stop at a local winery for a Vernaccia white tasting, capture photos of cypresses and farmhouses, and ride with six Vespas in the group.

Choose how you ride, from driving your own Vespa, sharing one as driver and passenger, or relaxing on the back as a passenger-only option.

Afternoon Vespa tour in Tuscan countryside

Expert guide

Orientation and driving test before departure

50cc Vespa scooter with automatic transmission

Third-party insurance, helmet, and fuel

Winery stop with Vernaccia white tasting

Cruise past vineyards, olive groves, villages

Views of hills around San Gimignano

Self-drive Vespa, shared Vespa, or passenger ride [as per option selected]

Gratuities

Hotel pickup from accommodation or Poggibonsi train station

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

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.

What to bring

Documents for drivers: Bring a physical ID (EU) or passport (non-EU), a valid driving license, and a credit card for the driver.

Credit card guarantee: Bring a valid credit card for a EUR 500 preauthorization per Vespa as a damage guarantee.

Clothing: Wear comfortable, breathable clothes such as jeans, leggings, or casual trousers and avoid short skirts or very loose items.

Jacket or raincoat: Carry a light jacket or raincoat, as it can get windy while riding even in summer.

Footwear: Wear closed-toe shoes like sneakers or flat shoes with good grip; do not wear sandals, flip-flops, or heels.

Spare clothes: Pack a set of spare clothes so you can change if you get wet in light rain.

What's not allowed

Document copies: Do not bring photocopies of IDs, passports, or driving licenses, as only physical documents are accepted.

Unsupported cards: Do not plan to use prepaid cards, American Express cards, or bancoposta cards for the Vespa guarantee.

Unsuitable footwear: Do not wear sandals, flip-flops, heels, or other open shoes, as these are not allowed for riding.

Additional information

Driving experience: Join this tour only if you have previous scooter, Vespa, or motorcycle driving experience, as it is mandatory.

Driving test: Expect a driving test before departure to verify that you can handle and feel confident on a Vespa.

Safety rule: If you cannot drive safely, you may ride as a passenger with a partner or be denied participation without reimbursement.

Age limits: Ensure drivers are at least 18 years old and passengers are at least 15 years old before booking.

Group size: Note that the tour operates only with a minimum of 4 participants in total.

Weight limit: Keep total rider and passenger weight on each 50cc Vespa within the recommended 160 kg (353 lbs).

Vehicle performance: Expect a maximum speed of about 48 km/h on flat roads and about 15 km/h on hills.

Height guideline: Avoid this tour if you are under 1.60 m (5'3''), as the 81 cm saddle height may be uncomfortable.

Light rain policy: In light rain, the tour runs as scheduled along the planned itinerary, so come prepared.

Heavy rain policy: In heavy rain, the same itinerary is carried out by minivan instead of by Vespa.

Wine stop: Be aware that the experience includes a stop at a local winery with Vernaccia white tasting.

Tour style: Remember this is a small-group Vespa tour, limited to a maximum of 6 Vespas in total.

Variant note: If you select the shared or passenger option, you will ride as described in that specific ticket choice.

Cancellation policy: For cancellations made at least 1 day / 24 hours prior to the tour, clients may receive a full refund minus a 10% administration fee.

Late cancellations: Cancellations made less than 1 day / 24 hours before the booked tour are not refundable, except for complex day trips involving train travel.