13 Vespa and Fiat 500 Tours in Chianti Worth Booking

1.Chianti Vespa Tour with Lunch from Florence & E-car Option

★★★★★★★★★★5.0 · 1,453 reviews · 6 hours 30 minutes (approx.) · from $125Our pick

Leave Florence by minivan for Chianti, then ride a classic Vespa or Fiat Topolino through vineyard roads with guides such as Yo, Julia, Haider, and Lorenzo. Expect a safety test, photo stops, winery visits, wine and olive oil tastings, and a Tuscan lunch.

“This was a 10/10 experience! The guides were so informative and personable, which made the trip even better. The only guide we recall is Haider, but there was a female guide as well but we did not catch her name. You take a bus to a parking lot to get you out of the city and familiar with the vespas prior to taking them out on the road. We appreciated the professionalism from the guides as they will make sure anyone who is driving is competent with the vespas to ensure everyone is safe. Then, you hit the road and get to spend a good amount of time to drive…”

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2.Tuscany Vespa Tours Through the Hills of Chianti

★★★★★★★★★★5.0 · 515 reviews · 6 hours (approx.) · from $193

Leave Florence at 8:30 for a guided Vespa ride through Chianti’s vineyard and olive groves. Ben, Filippo, Alessio, Leonardo, and other guides provide training, helmets, photo stops, and safety support before lunch, wine, and olive oil tasting at a Tuscan villa or castle.

“10 out of 10. A must do. Such a wonderful experience and our hosts were superb. Do yourself a favor and take this tour through the beautiful Tuscany countryside with this tour. So memorable and so much fun.”

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3.Tuscany by Vespa Full-Day Tour to Chianti Wine Region

★★★★★★★★★★4.7 · 475 reviews

Ride a 50cc Piaggio Vespa from Florence into Chianti with an English-speaking guide such as Cecilia, Haider, Lorenzo, or Charlotte. Expect a safety briefing, quiet country roads, Greve and Impruneta stops, and a 17th-century villa meal with wine and olive oil tasting.

“We had an absolute great time on our tour! Our guides were knowledgeable and very friendly. It was awesome to cruise through the countryside with the wind in your hair! One suggestion is that they make a couple stops to take pics of the views. The only picture stop was on a road lined with cypress trees. It was very pretty but I wanted pics of the rolling hills and vineyards.”

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4.All inclusive Tuscany Vespa Tour in Chianti

★★★★★★★★★★4.8 · 48 reviews · from $202

Leave Florence by air-conditioned transport for a small-group Vespa ride through Chianti. After a driving test, follow quiet country roads past vineyards and cypresses, admire San Gimignano, then share a Tuscan meal with wine and olive-oil tasting at a family winery. Guides include Vincenzo, Lorenzo, and Dom.

“Vincenzo was the best. The bus meeting point was far from the city center but understandable with the narrow roads. It was a perfect length drive on the Vespa and the wine region and hills were beautiful. Vincenzo made the trip though.”

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5.Classic Chianti Hills Fiat 500 Tour

★★★★★★★★★★4.5 · 33 reviews · 2 hours (approx.) · from $99Best value

Meet at Via Franceschi 23 in Scandicci for a hands-on introduction to a vintage Fiat 500. You’ll learn the double-clutch gearbox, follow a lead car through Chianti, and stop at Montegufoni and Strada in Chianti. Guide Bella has been praised for her friendly manner.

“So much fun!! Majestic rolling hills!! My wife and 2 kids had the biggest smile!! We had an absolute blast!! Staff was very friendly and easy going. We got right into it, would definitely do it again.”

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6.Chianti Countryside Full-Day Tour by Vintage Fiat 500

★★★★★★★★★★4.4 · 32 reviews · from $146

Drive an authentic restored Fiat 500 through Chianti with an English- or Italian-speaking guide. You’ll pass vineyards, cypress trees, farms, and medieval Castellina, then visit a winery for tasting. Guides such as Sara and Matilde help first-time Fiat drivers handle the car.

“Fabulous way to see some beautiful Tuscan landscape. Great winery lunch, great gelato & a very relaxing drive. Well worth taking this tour.”

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7.Vintage Fiat 500 Chianti & Tuscany Wine Tour

★★★★★★★★★★4.9 · 20 reviews · from $236

You’ll ride with a private driver in a fully equipped vintage Fiat 500 from central Florence into Chianti. Stop at a family-run farm for wine, olive oil, and a multi-course Tuscan lunch. Guides such as Iacopo and Nino lead in English or Italian. The car holds two guests plus the driver.

“This tour was the best. Nino took us out into the Tuscan countryside where we sampled wine, olive oil and a delicious lunch all made from produce from the farm. Nino was informative and engaging. A great tour. I strongly recommend.”

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8.Vintage Fiat 500 Wine Tour and Tuscan Lunch at Farm in Chianti

★★★★★★★★★★5.0 · 20 reviews · 4 hours (approx.)

Explore Chianti from Florence in a classic Fiat 500 with a private driver and English-speaking guide. Follow the scenic Chiantigiana road, stop at a family farm and winery, taste local wine and olive oil, and sit down to a Tuscan lunch. Guides may include Stefano, Toto, Bill, Jacopo, or Jessica.

“We were absolutely charmed by the stunning vineyards, olive groves, and winding roads that define this iconic Italian landscape. Our tour guide Toto was not only knowledgeable about the area's history and culture but also passionate about sharing it with us, also taking countless pictures for us. But it's not just about the destination; it's also about the journey. Feeling the wind in our hair on board of the vintage Fiat 500, a symbol of Italian craftsmanship and charm. Whether you're a car enthusiast or simply looking for a unique way to explore Tuscany, this experience is unforgettable. And let's not forget the culinary delights & wine tastings. With its…”

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9.Private Vespa Tour in Chianti from Florence

★★★★★★★★★★5.0 · 10 reviews · 6 hours (approx.) · from $473

Leave Florence at 9:00 am for a private six-hour ride through Chianti. With guides such as Giada, Gaia, Jessica, Samuele, Thomas, and Tommaso, you’ll visit Radda, Volpaia, and Panzano, then enjoy a winery lunch with wine, olive oil, and honey tastings. Scooter experience is required.

“Our tour guides (Thomas and Thomassa) were amazing! They were so patient with us as we attempted to learn how to ride the Vespas. When we decided it was not going to be a great idea to do that, they graciously agreed to drive us around Tuscany. They took us to so many villages and places to get the perfect photo. Our lunch was the most delicious meal we’ve had in Italy. Everything about the tour was PERFECT! I will recommend this private tour to anyone who wants to see the Tuscany region.”

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10.Chianti Self-Guided Vespa Tour with Lunch

★★★★★★★★★★3.6 · 8 reviews · from $168

Take an electric Vespa from Borgo Ognissanti into Chianti with an English app guide. Ride at your own pace through vineyards and olive groves, stop in Montefioralle and Greve, then enjoy a two-course Tuscan lunch with drinks. Advanced scooter experience, a smartphone, and a driving license are required.

“We picked up the scooter in the morning, which went quite smoothly before we could drive away. The lunch that is included was above expectations for me and the staff was nice. The area you drive through was very beautiful.”

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11.Chianti Hills: App‑Guided e‑Vespa Tour + Lunch in Greve

★★★★★★★★★★4.5 · 6 reviews · 8 hours (approx.) · from $133

Take an eight-hour, self-guided electric Vespa ride from Florence into Chianti. Your phone app leads you along vineyard roads to Montefioralle and Greve, where lunch at a traditional trattoria is included. You must be an experienced scooter rider, carry the required documents, and provide a €900 security deposit.

“Great tour, however highly recommend being comfortable driving a vespa. My only major recommendation is to take the time to completely map out the whole navigation and pay attention to all the turns. But in all great experience.”

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12.3-hour Vintage FIAT 500 Chianti Classico Private Wine Tour

★★★★★★★★★★5.0 · 4 reviews · from $194

Leave Florence in a vintage Fiat 500 with a private guide at the wheel. You’ll follow the scenic Chiantigiana road, visit a family-run farm, taste Chianti wine and olive oil, and enjoy local cold cuts. The three-hour tour is limited to six people and returns to its starting point.

“This was amazing! This was one of the highlights of our trip to Italy!!! This is a MUST if you want to experience all Italy can offer. Thank you - we will remember this day when we eat our own home made pasta”

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13.Full-Day Tuscany Vespa Tour in Chianti

★★★★★★★★★★5.0 · 3 reviews · 6 hours · from $168

Ride a Vespa through Chianti’s country roads with Angus, Ben, or Philipo, stopping for views before lunch, wine, and olive oil at Castello di Poppiano. The $168 price includes transfers, scooter, helmet, guide, tastings, and a light Tuscan meal.

“Run, don’t walk to this adventure. Angus, Ben and Philipo were a delight to meet. The ending lunch in castle Gucciardini was magical and their vast knowledge of the local wine and olive oil industry will make you feel richer for the experience.”

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