Best Siena Scooter Tours — the 4 We Would Ride

1.Vespa Tour with Lunch&Chianti Winery from Siena

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

Ride a Vespa in convoy through Chianti, with stops in Castellina, Radda, and Monteriggioni. You can drive if you are at least 18 with an international license and real scooter experience, or ride as a passenger from age 13. A winery visit, wine tasting, and light lunch are included.

“If you like Vespas, Vino and Vineyards, this is not to be missed!!! Our guide was amazing, the tour was fabulous, the winery we visited was gorgeous, lunch and wine tasting were delicious and the little towns we got to tour were breathtaking. I highly recommend this tour company - it was epic and fun and so worth the cost! BUT beware, you must pass a Vespa driving test before you they let you go!”

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

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

Join a small-group Vespa ride from Siena or Badesse through Chianti’s vineyard roads, with time in Castellina and a two-hour winery visit. You can drive your own automatic Vespa or ride as a passenger. Guides may include Sarah, Jonny, Sam, or Francesco.

“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.)

Ride a Vespa through Chianti on a private five-hour tour from Castellina. Guides such as Tommaso, Martina, and Stefani lead you to hill towns, viewpoints, lunch, and wine tasting. You need scooter experience, a driving license, and must pass the staff 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 7.5 hours riding or riding as a passenger through Chianti from San Gimignano. Follow a tour leader past vineyards, olive groves, Radda in Chianti, and Monteriggioni, then enjoy wine tasting and a light Tuscan lunch at Casale dello Sparviero. Drivers need scooter experience and a valid license.

“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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