The 4 Best Vespa Tours in Siena

1.Vespa Tour with Lunch&Chianti Winery from Siena

★★★★★★★★★★4.0 · 126 reviews · from $168Our pick

Ride a Vespa through the Chianti hills on a guided convoy from Siena, passing Monteriggioni, Castellina, and Radda. Stop at Casale dello Sparviero for a winery visit, tasting, and light lunch. You may drive if you have solid scooter experience, or ride as a passenger. An international driving permit and credit card are required for drivers.

“Riding behind my husband on the Vespa was a fun experience. He has experience of driving a motorcycle so he adapted well. Another guest who said they drove Vespas previously was denied driving one on the excursion due to safety concerns. We only stopped in 2 villages and 1/2 the ride was on beautiful country roads and the last 1/2 of the tour was in industrial areas. Wine tasting was not worth the stop. Two glasses were given to taste, both reds, and no tour of the winery itself. If it wasn't for the idea of getting lost, it makes more sense to rent a Vespa and tour the countryside…”

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2.From Siena/Badesse: Vespa & Chianti Tour in the Tuscan Hills

★★★★★★★★★★4.4 · 58 reviews · from $123Best value

Spend four hours riding an automatic Vespa through the Chianti hills from Siena or Badesse. Choose to drive or ride as a passenger, stop in Castellina in Chianti, then visit a farm winery for regional wines and dry snacks. Guides including Sarah, Jonny, Sam, and Francesco have led this route, with English and Italian tours available.

“A bit disorganized in the beginning getting bikes and helmets and taking the pre-ride test. Need a better system for evaluating riders abilities. Seemed a bit geared toward men riders with little patience for the woman who wanted to ride and we’re unable due to a 1 minute eval. Overall great experience for all though!”

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3.Private Vespa Tour in Chianti

★★★★★★★★★★4.5 · 8 reviews · 5 hours (approx.)

Start in Castellina at 10 a.m. for a five-hour private Vespa ride through Chianti. You choose the stops, visit historic villages, and pause for lunch and wine. Guides such as Tommaso, Martina, and Stefani lead the route, but you need scooter experience, a license, and approval after the safety briefing.

“This is a “Must Do”. So much fun! Our guide, Tommasso was fabulous. I wasn’t sure what to expect but this tour was a highlight of our Italy vacation. We drove Vespas to a couple ancient castle villages then Tommasso gave us personal tours on foot. He was passionate and knowledgeable about their history. All was very interesting. The lunch we were treated to at the end was a special treat. I highly recommend this tour.”

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4.Full-Day Chianti Tour by Vespa Scooter from San Gimignano

★★★★★★★★★★3.5 · 7 reviews · from $168

Spend about 7.5 hours riding through Chianti from San Gimignano, as a passenger with an escort driver or as your own Vespa driver. You’ll pass vineyards, olive groves, cypress roads, Radda in Chianti, and Monteriggioni, then stop at Casale dello Sparviero for wine and a light Tuscan lunch. A license and scooter experience are required to drive.

“There was an accident on the tour and thus I did not take it. Instead, I went on an excursion with two other people in a Fiat.”

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