Day Trips

Tuscany Private Vespa Tour with Lunch and Wine Tasting

Enjoy a private self-drive through the Tuscan hills, riding your own Vespa between vineyards and stone villages for a relaxed countryside escape.

Start at the Tuscany on Wheels office with free parking, take a brief orientation and driving test, then get your helmet, insurance, fueled scooter, and go.

Ride in a convoy of 50cc automatic scooters along olive groves and the hills around San Gimignano, following quiet stretches of Chianti countryside.

Pause at a local winery for a Tuscan lunch with tastings, while your dedicated tour leader shares stories and photo stops along the route.

Private Vespa tour through the Chianti countryside

Expert guide

Orientation and driving test before departure

Third party insurance, helmet and fuel

Typical Tuscan lunch with wine tasting in a local winery

Cruise around rolling vineyards, olive groves, medieval villages and the hills around San Gimignano

50cc Vespa scooter with automatic transmission

Free car parking available at the Tuscany on Wheels office

Hotel pickup and drop-off

Pick-up from your accommodation or from Poggibonsi train station is available upon request (subject to availability) and is not included in the tour price

Repair costs in case of damages caused to the Vespa

You can cancel these tickets up to 48 hours before the experience begins and get a full refund.

Ride a private Vespa through the Chianti countryside with a dedicated local tour leader, plus a Tuscan lunch with tastings.

Getting started

Arrive at the Tuscany on Wheels office, where free car parking is available if you are arriving by car. Check in, meet your expert guide, and complete the mandatory orientation and driving test before departure. After your documents are verified and you are matched with your 50cc Vespa scooter with automatic transmission, collect your helmet and get ready to leave.

What to expect

Chianti countryside Vespa ride

Features

Travel on a private Vespa tour through the Chianti countryside, cruising along roads that pass rolling vineyards, olive groves, and medieval villages. The route also offers views of the hills around San Gimignano, giving you plenty of chances to pause for photos.

Use a 50cc Vespa scooter with automatic transmission, which is provided for the tour so you can focus on the ride rather than on gear changes. Third-party insurance, helmet, and fuel are included, so you do not need to arrange these separately.

Follow a dedicated local tour leader who sets the pace and leads the way through Chianti, sharing local knowledge while you ride in a small convoy of up to 8 Vespas. The experience is designed as a private outing, suitable for couples, families, or small groups who want a personalized route.

Tuscan winery lunch and tasting

Features

Stop at a local winery for a typical Tuscan lunch with tastings in a relaxed rural setting. You have time here to sit down, eat, and sample regional spirits before continuing the ride.

After lunch, continue your cruise around the vineyards and olive groves surrounding the winery, rejoining the scenic roads with your guide. The Vespa use, along with insurance, helmet, and fuel, remains covered for the entire guided portion of the experience.

Wrapping up

The guided ride concludes back at the Tuscany on Wheels office, where you return your Vespa, helmet, and any provided gear before departing independently.

What to bring

Documents: Bring your physical ID or passport, valid driving license, and credit card; photos or copies aren't accepted.

Credit card: 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.

Outerwear: Bring a light jacket or raincoat since it can get windy while riding.

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

Spare clothes: Pack a spare set of clothes in case of light rain during the ride.

Rain protection: Bring a raincoat because the tour runs regularly in light rain.

What's not allowed

Photo documents: Do not rely on photos or photocopies of your ID, passport, or driving license, as they aren't accepted.

Card types: Do not bring prepaid cards, American Express, or bancoposta cards for the Vespa guarantee.

Inappropriate clothing: Avoid short skirts or very loose clothing that may be unsafe while riding.

Open shoes: Do not wear sandals, flip-flops, or heels, since closed-toe shoes are mandatory for driving.

Additional information

Driving experience: You must have previous scooter, Vespa, or motorcycle driving experience to join as a driver.

Driving test: A driving test is carried out before departure to confirm your ability to ride safely.

Safety rule: If you can't drive safely, you may ride as a passenger or won't be allowed to join the tour.

Age requirements: Drivers must be at least 18 years old and passengers at least 15 years old.

Group size: The tour runs with a maximum of 8 Vespas and up to 16 participants in total.

Weight limit: The recommended maximum combined weight on each 50cc Vespa is 160 kg.

Vehicle speed: The Vespa's top speed is about 48 km/h on flat roads and 15 km/h on hills.

Height guidance: The 81 cm saddle height isn't recommended for people shorter than 1.60 m.

Weather changes: In light rain, the tour continues; in heavy rain, the itinerary may switch partly or fully to a minivan.

Cancellation policy: Full refund for cancellations made at least 1 day / 24 hours prior to the tour, minus a 10% administration fee. No refund for cancellations made less than 1 day / 24 hours before the booked tour, except for complex day trips involving train travel.