Pick a Pour: 10 Vineyard Bike Tours in Florence

1.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours · from $144Our pick

Leave Florence by minivan for a guided 35-kilometer ride through Chianti, Impruneta, and Chiocchio. Choose a 50cc Vespa, electric Vespa, Piaggio Zip, or Fiat Topolino. After quiet country roads and a medieval village stop, tour a winery, taste wine and olive oil, and share a typical Tuscan meal with guides such as Niccolò, Julia, or Yo.

“Absolutely incredible experience! Niccolo and Julia were amazing guides. You get a little tutorial to learn how to ride the Vespa and then you get to ride the Vespa around Chianti with beautiful views for about 2 hours! The included lunch and wine were great.”

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2.Tuscany Vespa Tour: Lunch & Wine Tasting, Countryside Roads

★★★★★★★★★★5.0 · 614 reviews · 5 hours (approx.) · from $228Top rated

Leave Florence by air-conditioned minivan with guides such as Luca, Alexa, or Dejan, learn to handle an automatic Vespa, and ride through Chianti’s hills, vineyards, and olive groves. Finish at a family-run winery with a cellar visit, wine tasting, olive oil, and a traditional lunch. Riders who lack confidence can ride as passengers.

“Great experience. Nice to get out of busy city and see countryside on a Vespa. Small winery from 1300s, very friendly staff. Luca was fantastic! Highly recommend this experience.”

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3.Tuscany Vespa Tour from Florence with Wine Tasting

★★★★★★★★★★5.0 · 425 reviews · 7 to 8 hours (approx.) · from $241

Spend 7 to 8 hours riding a Vespa through the Tuscan hills, visiting medieval San Gimignano, and sharing a local winery lunch with Chianti pairings. Guides such as Daniel, Cecilia, Marco, and Daniele help you practice, stay safe, and enjoy the day. Drivers need an original license and must be at least 18.

“The Vespa tour with Max & Daniel was even BETTER THAN EXPECTED. WOW the views in the Tuscany countryside will leave you breathless. San Gimignano is one of a kind with St. Matthew & St. John’s gates. The dining experience was over the top incredible with personable Italian family hospitality. Barcelona Vibes Max & Daniel!!! LOL”

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4.Small Group Vespa Tour Tuscany Winery & Lunch

★★★★★★★★★★4.9 · 268 reviews · 7 hours · from $235

Leave Florence in a small group of up to eight, learn to ride a Vespa on quiet Tuscan roads, and travel through Chianti to San Gimignano. Guides such as Lorenzo, Cecilia, Daniel, and Mido help nervous riders feel safe. Finish with a Tuscan lunch and wine tasting at a local winery with broad countryside views.

“This trip was so much fun!! Everything was planned out so well and the tour guides were fantastic. I rode with Lorenzo (the best tour guide) because I was not comfortable driving myself, and it honestly was even better because I didn’t have to worry about a thing and could just take in the scenery! Stopping at the town halfway was great too, because I wouldn’t have had an opportunity to see it while in Italy (plus the famous gelato shop was so good!). The vineyard was also beautiful with lots and lots of wine! And the meal was also great. Our group got along really well, which made for…”

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5.Chianti E-Bike Tour with Lunch & Two Wine Tastings

★★★★★★★★★★4.7 · 231 reviews · 6 hours · from $116

Ride from Florence into Chianti with a small group of up to 12, using pedal-assist e-bikes on hilly country roads. Guides such as Grace, Marco, Francesco, Alex, and Yo share local stories while you stop for views, visit a winery, taste Chianti Classico, eat a Tuscan lunch, and finish with another tasting at CiaoFoodies Hub.

“Everything about this experience was wonderful. Our guide was great, cheerful knowledgeable and took really good care of our group. The ride from central Florence up to the Chianti hills and back was excellent! We stopped a few times along the way to have a rest and take pics. Such beautiful scenery. The winery lunch was lovely as was our final stop at a wine bar in Florence. The downhill rides were great fun! Some of the hills were a little challenging but do-able with an e-bike. We visited Michaelangelo lookout on the way back which has excellent views over Florence. Highly recommend this experience.”

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6.Tuscany Bike Tour with Wine & Olive Oil

★★★★★★★★★★4.9 · 174 reviews · 4 hours · from $100Best value

Ride 11 km through Florence’s hills and Tuscan country lanes with a local English or Italian-speaking guide. Expect four gradual climbs, historic villas, olive groves, and a stop at a villa or trattoria for Chianti, extra virgin olive oil, bread, and Tuscan cold cuts. Regular bikes are included, while e-bikes cost €20 extra.

“The tour was breathtaking and Claudio was articulate and knowledgeable.”

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7.Florence/Badesse: Tuscany Group Vespa Tour with Wine Tasting

★★★★★★★★★★4.4 · 56 reviews · from $123

Ride an original automatic Vespa through Chianti’s vineyards, olive groves, chestnut woods, and medieval villages. An English or Italian-speaking guide leads the way to Castellina in Chianti and a scenic winery for a guided visit and tasting. You can drive, share a Vespa, or request the exclusive driver option.

“My family of 7 has a wonderful time exploring the little towns of Tuscany. This is the perfect day adventure for anyone looking to see the iconic rolling hills of Tuscany. There is nothing better than riding a Vespa through the Chianti region see little towns and hidden gems of the region. Our guide Diego was amazing and taught us about the region and knew all the good spots to go. This tour was worth the money and I would recommend to anyone staying in the region.”

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8.Tuscany Vespa Tour with Lunch & Wine

★★★★★★★★★★4.8 · 54 reviews · 7 hours · from $210

Spend seven hours riding a 50cc automatic Vespa through quiet Chianti roads near San Gimignano. After a Florence transfer, safety briefing, and driving test, you’ll stop at a family-run winery for a Tuscan lunch, wine, and olive oil tasting. Small groups, usually limited to seven, make the ride personal, with guides such as Vincenzo and Emiliana leading the way.

“Highly recommend! Such a fun day despite the rain. It takes 40min to get to the Vespas from Florence, and then there is paperwork and test driving but then you're off riding! Our guide, Vincenzo, was amazing guide! He was so sweet, fun, professional and caring. We ran into rain and stopped at a winery to wait it out. He was genuinely bummed and was determined to get us on the road. After an amazing lunch with wine tasting(so fun and delicious!) we were back on the road in the Tuscan countryside. It was so beautiful. And you're back in time for aperitivo and dinner. What a great experience!”

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9.Chianti E-Bike Tour with Tuscan Lunch & Winery

★★★★★★★★★★5.0 · 42 reviews · 7 hours · from $175

Ride from Florence’s Oltrarno into Chianti Classico with a small group of up to 10. Guides such as Ale, Claudio, Giovanni, and Andrea lead you along country roads to a family-run farm for homemade lunch, wine, and olive oil tasting. Expect hills, scenic stops, and some city traffic.

“The tour was fantastic from start to finish. My wife and I chose the full-day option and were treated to some truly stunning views. Lunch at the farm was delicious and full of flavor. Our guide, Andrea, was outstanding—since we were the only ones on the tour, he was able to take us to a few extra spots. The e-bikes made the ride both easy and enjoyable. Highly recommended!”

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10.Chianti Hills Bike Tour with Farm Lunch & Wine

★★★★★★★★★★5.0 · 32 reviews · 7 hours · from $152

Leave Florence’s Oltrarno district by bike and ride into the Chianti hills with an English-speaking guide. You’ll visit a family-run farm, tour its wine and olive oil operation, and enjoy a Tuscan lunch with tastings. Expect strong climbs, a small group of up to eight, and a mostly downhill return. E-bikes cost €25 extra.

“Lorenzo fantastic guide and adapted the course to fit levels of fitness spot on and still stretched us thanks”

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