Best Vespa Tours in Siena — Our Top 9

1.Vespa Tour with Lunch&Chianti Winery from Siena

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

Ride in a guided Vespa convoy from Siena through Chianti, with stops in Castellina, Radda, and Monteriggioni. At Casale dello Sparviero, tour the winery, taste Tuscan wines, and eat a light lunch. You may drive solo or ride with an escort, but scooter experience is required.

“The worst experience ever. Suppose to be a guided tour and only thing he did was ride his Vespa in front of not a word spoken. When we returned the Vespa we were told that we damaged it and demanded payment. This company is run by thieves. Please beware very unscrupulous and not worth the money!!!”

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

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

Ride an automatic Vespa through the Chianti hills from Siena or Badesse, stopping in Castellina in Chianti and at a local winery. You can drive or ride as a passenger. Guides such as Sarah, Jonny, Sam, and Francesco have led the route, which blends scenic roads, free time, wine, olive oil, and local snacks.

“We loved our tour! It ended up just being us, our guide, and one other couple. We’d never ridden vespas before but my husband picked it up really quickly. Our guide was great too. He gave us a small amount of history about each hill town we stopped in and then let us explore on our own. It was the perfect mix of “guided” and self exploring. We loved the winery we stopped at for a quick tour and tasting too. Perfect amount of time on the Vespa without feeling like it was dragging on. I’d highly recommend this tour!”

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3.Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

★★★★★★★★★★4.5 · 52 reviews · from $191

Take the wheel of a vintage Fiat 500 and follow your guide through Castellina, Radda, and the Chianti hills. Stop at Monteriggioni, then enjoy a winery visit, wine tasting, and light Tuscan lunch. Manual driving experience is required, and pickup from Siena may cost extra.

“Even when we had a good time. The Fiat 500 we arranged for the tour many of them were out of service. They give us a Polaris when we asked if there had another type of car in order to us not to loose the tour. (The Fiat need maintenance. )”

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4.Day Tour in a Vintage Fiat 500 with Winery

★★★★★★★★★★4.4 · 41 reviews · from $146

Drive a manual vintage Fiat 500 from Siena through the Chianti Hills, with stops in Castellina and an exclusive winery. Guides such as Lorenzo, Francesco, Gabriele, and Sam lead the four-hour small-group outing in English or Italian. Bring a license and credit card if driving.

“It was really wonderful, sam was the perfect guide for showing us around the beautiful toskana”

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5.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. Your guide leads you to Radda, Panzano, and other historic stops, with time for village walks, an Italian lunch, and wine tasting. Tommaso, Martina, or Stefani may lead the day.

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

★★★★★★★★★★3.5 · 7 reviews · from $168

You’ll travel from San Gimignano into Chianti by minivan, then ride an automatic Vespa through vineyards, olive groves, and villages such as Radda and Monteriggioni. Choose to drive or ride with an escort, and stop at Casale dello Sparviero for wine and a light Tuscan lunch.

“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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7.Chianti Vespa Tour

★★★★★★★★★★5.0 · 5 reviews · 4 hours (approx.) · from $129Top rated

Drive a Vespa along Tuscany’s Chiantigiana road, visit Castellina in Chianti, and taste wine at a local winery. Guides such as Jojo and Gabriel help with the route and driving, but you need a valid license, credit card, and real scooter skills. Pickup from Florence costs extra.

“Driving Vespas requires skill. my adult sons could not get it. Driving with a person on the back is even harder. The lady in the other group smashed into a group of parked vespas.Thankfully, Gabriel saved the day by putting the 5 of us in an open air jeep and we had the best time! They should advertise that jeep.”

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8.Fiat 500 Tour of the Chianti Roads from San Gimignano

★★★★★★★★★★5.0 · 4 reviews · from $191

Follow a guide through Chianti in an original manual Fiat 500, stopping at Castellina, Monteriggioni, and Casale dello Sparviero winery. The seven-and-a-half-hour trip includes a light Tuscan lunch, winery tour, and tasting. Drivers need a license, manual-car skills, and a credit card guarantee.

“Late late review BUT what an amazing experience that was. My husband and I visited Tuscany last August and booked a tour that included a vintage Fiat to be driven through the Tuscan Hills. We had an amazing tour guide whom chaparoned us while driving a Vespa. It was quite the experience of a lifetime never to be forgotten! Highly recommend it!”

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9.Private Vintage Fiat 500 tour in Chianti

★★★★★★★★★★5.0 · 2 reviews · from $392

Take a private six-hour Fiat 500 tour through Chianti with a guide such as Thomas, Filippo, or Gabriele. Visit Castellina, Radda, and Panzano, then enjoy a traditional Tuscan lunch and wine tasting at a 200-year-old villa. A valid driver license is required.

“What an awesome experience! Would do it again! Was so much fun!! Thomas was a great tour guide. Would def recommend him! Lunch and wine ended it off so well! Def 5*****”

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