Vespa Tours · FLORENCE

Vintage Fiat 500 Tours in Florence: the 15 Best Rides

25 tours  ·  from $99 a head

This is the shortlist worth sending a friend: 15 vintage fiat 500 tours in Florence that earn the morning, each with its price, its rider verdict and the one thing to know before you commit.

Florence: Chianti Wine Region Vespa or Fiat Topolino Tour - Leaving Florence for the Chianti hills
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Florence: Chianti Wine Region Vespa or Fiat Topolino Tour

1.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours Our pick

Leave Florence by minivan for a guided ride through Chianti, Impruneta, and Chiocchio. Choose a 50cc Vespa, electric Vespa, Piaggio Zip, or Fiat Topolino. Expect quiet roads, a medieval village, a winery visit, Tuscan food, wine, olive oil, and guides such as Niccolò, Julia, Yo, and Heather.

“Heather and Yo took the time to help me feel comfortable with the Vespa. We had a great group, so much fun!”

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Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Hills and Italian Cuisine - Piazzale Michelangelo and San Miniato al Monte
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Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Hills and Italian Cuisine

2.Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Hills and Italian Cuisine

★★★★★★★★★★5.0 · 719 reviews · 6 hours (approx.) · from $160Top rated

Take the wheel of a manual 1960s Fiat 500 on a guided route from Florence into the Tuscan hills. Guides such as Ado, Chris, Leo, and Alex handle the convoy, radio support, and driving briefing. Expect scenic stops, San Miniato al Monte, and a Tuscan meal.

“This was such an amazing experience. Meeting location was easy to find and transportation to garage was smooth. Our guide Ado was exceptional and made the experience worth it providing us with insightful facts at each stop. The Fiat 500 was clean and was great everything worked with no issues. Our tour guide Ado gave us walkie talkies to communicate in case we encountered any issues (such as stalling the vehicle). We made a couple stops before eating at a restaurant with such an amazing view. Would recommend this to anyone trying to see the Tuscany region.”

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Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience - The convoy drive through the Chianti hills
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Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

3.Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

★★★★★★★★★★5.0 · 660 reviews · 4 hours (approx.) · from $139

Drive a restored 1960s Fiat 500 from Scandicci into the Chianti hills with a guide leading the convoy. After scenic country roads and photo stops, visit a 15th-century wine estate for tastings and a light lunch of Tuscan meats and cheeses. Manual driving skills are essential.

“Must know how to drive a manual! Cars are not automatic! Other than that it was a great experience. I would recommend to anyone staying in Florence!”

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Florence: Countryside Vintage Fiat 500 Driving Tour - Meeting the group at Santa Maria Novella
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Florence: Countryside Vintage Fiat 500 Driving Tour

4.Countryside Vintage Fiat 500 Driving Tour

★★★★★★★★★★4.8 · 232 reviews · 5 hours · from $153

Take the wheel of a restored 1960s Fiat 500 and follow an English-speaking guide from Florence into the Tuscan hills. You’ll drive narrow lanes, stop at an old church and scenic overlooks, then enjoy Tuscan ham, cheese, and Chianti on a private terrace. Manual driving experience is required.

“Chris, Gabi and the team made this a memorable experience - highly recommended! The green 500 was a favorite!”

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Florence Wine Tasting and Tuscan Lunch in a Vintage Fiat 500 - Meeting the Fiat 500 in Scandicci
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Florence Wine Tasting and Tuscan Lunch in a Vintage Fiat 500

Self-Drive Vintage Fiat 500 Tour from Florence: Sunset Drive and Aperitivo - Following the guide into the Chianti hills
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Self-Drive Vintage Fiat 500 Tour from Florence: Sunset Drive and Aperitivo

6.Self-Drive Vintage Fiat 500 Tour from Florence: Sunset Drive and Aperitivo

★★★★★★★★★★4.5 · 61 reviews · 3 hours (approx.) · from $149

Drive a manual vintage Fiat 500 in a guide-led convoy from Scandicci into the Chianti hills. Guides such as Bella, Nico, Carlo, and Mattia provide patient instruction, photo stops, and local insight before aperitivo, Tuscan snacks, and Chianti wine.

“Bella and Phillipo were lovely and we had a great time cruising the hills of Tuscany in our vintage Fiat 500. Our 6 year old loved it too!”

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Self-Drive Vintage Fiat 500 Tour: Gourmet Lunch and Wine Tasting - Meeting Bella and learning the old cars
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Self-Drive Vintage Fiat 500 Tour: Gourmet Lunch and Wine Tasting

7.Self-Drive Vintage Fiat 500 Tour: Gourmet Lunch and Wine Tasting

★★★★★★★★★★5.0 · 57 reviews · 4 hours 30 minutes (approx.) · from $199

Meet Bella and her team outside Florence, learn to handle a manual vintage Fiat 500, and follow the lead car through Chianti country. Stop for photos, then enjoy lunch, local wine, olive oil, and family hospitality at a villa before returning to the meeting point.

“This trip was fantastic. Very well organised, the cars were in fantastic condition and the views driving around Tuscany were exceptional. The lunch was very nice, lots of local fresh produce and plenty of wine to wash it down! We had a good chat and laugh with the other people on the tour. The double clutch took a bit of getting used too but after that it felt really special to be driving around Tuscany in a piece of history. Especially with the excellent music playing to accompany us!”

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Classic Chianti Hills Fiat 500 Tour - Rolling out toward the Chianti hills
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Classic Chianti Hills Fiat 500 Tour

8.Classic Chianti Hills Fiat 500 Tour

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

Meet in Scandicci at 9:00 am for a hands-on introduction to a vintage Fiat 500, then follow a guide car through Chianti. You’ll stop at Montegufoni and Strada in Chianti for views, photos, and local commentary. Bella has hosted this route, and cars may include the pink Fiat Isabella.

“The worst tour experience we have aver had. Chianti hills fiat 500 tour operators were a no show after taking a taxi ride out to the meeting location. Wasters 100$ on taxis and 4 hours of vacation time to find no one at the meeting location. While looking at reviews after this meeting experience we found this was not the first time. This group should be removed form the list of tour operators Viator uses.”

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Chianti Countryside Full-Day Tour by Vintage Fiat 500 - The four-hour route through the Chianti hills
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Chianti Countryside Full-Day Tour by Vintage Fiat 500

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

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

Take the wheel of a restored Fiat 500 for a four-hour drive through Chianti’s vineyards, cypress-lined roads, and medieval villages. Your English- or Italian-speaking escort leads the way to Castellina and a winery tasting. Guides such as Sara and Matilde are praised for patient driving help.

“We had a very good time. Using a vintage car to explore the Chianti area added more to its atmosphere. I can only recommend this!”

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Florence: Vintage Fiat 500 Tour with Chianti Winery & Lunch - Leaving Florence for the Chianti hills
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Florence: Vintage Fiat 500 Tour with Chianti Winery & Lunch

10.Vintage Fiat 500 Tour with Chianti Winery & Lunch

★★★★★★★★★★5.0 · 24 reviews · 4 hours · from $234

Leave Florence with a private driver in a classic Fiat 500 and follow old roads through Chianti vineyards and olive groves. Stop above Florence for a local view, then visit a family-run farm for a multi-course lunch, Chianti wine, and extra virgin olive oil tastings. The car holds two guests plus the driver.

“Virginia gave us a wonderful experience driving through the country side of Tuscany. Luciano winery was amazing.”

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Florence: Private Vintage FIAT 500 with Wine & Olive Oil - San Miniato al Monte in 20 minutes
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Florence: Private Vintage FIAT 500 with Wine & Olive Oil

11.Private Vintage FIAT 500 with Wine & Olive Oil

★★★★★★★★★★4.5 · 21 reviews · 2 hours (approx.) · from $204

Ride in a classic Fiat 500 from Florence through the Tuscan hills, stop at San Miniato al Monte, and enjoy rustic bread with extra-virgin olive oil and a glass of Chianti. The private format keeps the outing personal, with guides including Stephano, Dimitri, Lorenzo, and Francesco named in guest feedback.

“Great fun. I am not a wine drinker personally which is ironic since you do a wine tasting but i still enjoyed the food- pasta mostly. the best part was driving the fiats around and seeing the views of chianti and then getting to stop at two towns and also take some quick photos. Our instructors were a good laugh too”

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Vintage Fiat 500 Wine Tour and Tuscan Lunch at Farm in Chianti - Starting in Florence at Via del Campuccio
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Vintage Fiat 500 Wine Tour and Tuscan Lunch at Farm in Chianti

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

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

Take a chauffeured vintage Fiat 500 from Florence into Chianti, with a guide such as Stefano Nino, Toto, or Bill. Expect winding roads, vineyard and olive-grove views, a family farm, wine and olive oil tasting, and a traditional Tuscan lunch. Customers do not drive.

“This was such a great experience! Riding in a fiat from the 70s was an adventure in and of itself--these cars are small and low to the ground. We took a scenic drive to get some great views of the city and took in the countryside. Our guide was so kind and generous with conversations. The winery was very beautiful and the food amd wine pairings exceeded expectations. We will definitely be recommending this trip to friends.”

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Discover Florence city center on e-cabriot fiat 500 - Santa Maria Novella and the medieval Ponte Vecchio
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Discover Florence city center on e-cabriot fiat 500

13.Discover Florence city center on e-cabriot fiat 500

★★★★★★★★★★5.0 · 19 reviews

Ride through Florence in a restored electric Fiat 500 Cabrio with a private driver-guide. In two hours, you’ll see the Duomo, Santa Croce, Ponte Vecchio, Piazzale Michelangelo, San Miniato al Monte, and more, with pickup, water, and a souvenir photo included.

“10/10 experience. Our guide was an excellent driver, nice, knowledgeable, and patient with us as we took photos. Worth every € and took us to every spot someone would want to see in Florence.”

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Florence: Vintage Fiat 500 Tour with Wine Tasting at Winery - Starting on Via del Campuccio
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Florence: Vintage Fiat 500 Tour with Wine Tasting at Winery

14.Vintage Fiat 500 Tour with Wine Tasting at Winery

★★★★★★★★★★4.9 · 17 reviews · 2 hours · from $152

Ride as a passenger in a vintage Fiat 500 with a private English or Italian-speaking driver. You’ll visit San Miniato al Monte, follow quiet roads above Florence, and stop at a family-run winery for local wine, olive oil, cold cuts, and bread.

“Beautiful experience! Alessandro and Giacobbe did an amazing job showing us the country side of Firenze in these beautiful vespas. The stops and the olive oil breakfast experience was a treat! Thank you again!”

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Florence Vintage Fiat 500 Tour with Wine Tasting at Farm - Meeting your guide near Santo Spirito
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Florence Vintage Fiat 500 Tour with Wine Tasting at Farm

15.Florence Vintage Fiat 500 Tour with Wine Tasting at Farm

★★★★★★★★★★5.0 · 17 reviews · 2 hours (approx.) · from $155

Let a local guide drive you in a fully equipped vintage Fiat 500 from Florence into the nearby Tuscan hills. Stop at San Miniato al Monte for a superb city view, then visit a family-run farm for wine and extra-virgin olive oil tasting. Morning trips include breakfast, while afternoon departures offer gelato.

“Our guide Gabriel was awesome. We could’ve hung out with him all day. He provided lots of info in the area and brought us to some unexpected spots. He also took great photos of us along the way. The vintage Fiat definitely got reactions from onlookers. Having a driver rather than driving yourself made for a much more relaxing ride.”

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