Top 10 Cycling and Wine Tours in Florence

1.Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

★★★★★★★★★★5.0 · 1,300 reviews · 6 hours (approx.) · from $145Our pick

Leave Florence by van for a guided ride through Chianti’s vineyards, olive groves, and country lanes. Guides such as Ben, Filippo, Angus, and Alessio lead about two hours of cycling, with a support van for the steepest hill. Finish at a medieval castle with wine, olive oil, and a Tuscan lunch. E-bikes cost extra.

“We loved biking through the hills of Tuscany. The guides were amazing since they catered to many levels of cyclists and different bikes.”

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2.Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

★★★★★★★★★★5.0 · 775 reviews · 4 to 7 hours (approx.) · from $96

John from E-Bikes Florence sets you up with a pedal-assist bike, helmet, phone holder, and GPS route. You ride from Florence through Fiesole and the Tuscan hills to a family-run vineyard, where wine, olive oil, and picnic foods are available to buy. The route is independent, scenic, and hilly.

“Fantastic adventure and scenery. Well marked bike route map. John was very informative and prepared us well.”

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

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

Ride from central Florence into the Chianti hills with an English- or Spanish-speaking guide such as Grace, Marco, Yo, or Francesco. Expect roughly 35 to 50 kilometers of cycling, quiet lanes, steep sections made easier by pedal assist, a winery visit with lunch, and a second tasting at CiaoFoodies Hub.

“This was one of the most memorable experiences we have had on our European holiday. Our guide - Michaela was outstanding making sure we were all safe riding along the narrow roads and keeping us informed on historical facts. I would highly recommend this tour to all my active friends and family. The lunch, wine tasting and making new friends was truly special. 10/10 👍”

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4.Tuscany Bike Tour with Wine, Oil and Food in the Florentine Hills

★★★★★★★★★★5.0 · 209 reviews · 4 hours (approx.) · from $95

Ride a geared touring bike from Florence’s Oltrarno through Porta Romana, Medici estates, Arcetri, vineyards, and olive groves. Guides such as Giuseppe, Eli, Claudio, and Alessandro share local stories before a farm stop with Chianti, olive oil, bread, cheese, cold cuts, and honey. Expect four hills and about four hours of riding.

“Excellent tour of the Tuscan country side with wine tasting. Giuseppe was a wonderful and knowledgeable guide and my daughter and I were lucky to have his undivided attention. Just the three of us on this tour. Scenery amazing on bikes. Highly recommend.”

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5.Tuscany Bike Tour with Wine & Olive Oil

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

Ride 11 km through Florence’s southern hills with guides such as Giuseppe, Claudio, Luca, or Ale. Expect four gradual climbs, quiet country roads, views of Villa Poggio Imperiale and San Miniato al Monte, then a family-run tasting of Chianti, olive oil, bread, cheeses, and Tuscan cold cuts. Regular bikes are included, with e-bikes available for €20.

“Our guide Jack was a wonderful guide, full of history and humor! The tour took us on a beautiful path along the Tuscany countryside, with breathtaking views and delicious snacks of fresh olive oil, honey meats and cheeses. The rainy weather didn’t hinder our experience at all! Highly recommend this tour group, We Love Tuscany, to anyone wanting an inspiring experience to make you feel like you are really getting a piece of the beauty of Firenze and Tuscany!”

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

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

Spend seven hours cycling from Florence’s Oltrarno into Chianti Classico with a small group of up to 10. Your guide, possibly Ale, Giovanni, Claudio, or another local leader, handles the route and safety. Ride an e-bike through olive groves and villages, then enjoy a farm lunch, wine, and olive oil tasting.

“We had a wonderful time, our guide was extremely knowledgeable and very helpful. The lunch and wine tasting were amazing. The bikes were easy to ride and our guide explained how to ride safely. This tour was a highlight of our trip and we would highly recommend it!”

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7.Tuscany Hills Bike Tour with Lunch at farm and Wine Tasting

★★★★★★★★★★4.9 · 18 reviews · from $73

Ride from Florence into the Chianti Classico hills with a professional English or Italian-speaking guide. You will cover 35km with 460m of climbing, stop for a Florence viewpoint, then enjoy lunch, wine, and olive oil at a family-run farm. Regular bikes are included, while limited e-bikes cost €30 extra.

“If you are at least a decent cyclist and a lover of great views, culture and great people- this will be the highlight of your vacation! The only warning I have for you has nothing to do with the tour. If you are driving to the start of the tour on the southern side of Florence, give yourself an extra half hour to find parking. Know where none residents can park. We were late to the start location due to parking the car. We did contact the office and they kindly gave us advice and helped us find their office after parking.”

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8.Chianti E-Bike Tour with Wine Tasting and Lunch

★★★★★★★★★★4.8 · 16 reviews · 5.5 hours · from $117

Meet your guide at E-Dway Authentic Experience in central Florence, learn your e-bike, then ride toward Poggio Imperiale, Pozzolatico, and the Chianti Hills. Guides such as Luigi, Ovidio, and Dimitri lead the route, which combines paved roads and dirt tracks with a farm lunch and biological wine tasting near Impruneta.

“Loved the tour, excellent guide, high quality bikes, incredible route and views, lovely lunch. I might even sign up to do it again. Highly recommend!”

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9.E-Bike Tour in Tuscany with Winery & Wine Tasting

★★★★★★★★★★4.9 · 15 reviews

Leave Florence’s Oltrarno by E-bike for four hours of hill roads, villas, olive groves, and city views. Your English-speaking guide leads a group of up to 10 to a family-run winery for wine, olive oil, bread, and a Tuscan appetizer. Guides have included Luka, Amar, Totò, Jack, Claudio, and Giovanni.

“Luka was an amazing and thoughtful guide. This outing was our favorite of all during our 2 weeks in Europe.”

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10.Florence at Night Bike Tour with Wine and Aperitivo Picnic

★★★★★★★★★★4.7 · 13 reviews · 2.5 hours · from $69Best value

Ride through Florence’s San Frediano, Santo Spirito, San Niccolò, and Santa Croce with an English-speaking local guide. You’ll follow the Arno at sunset, stop for Tuscan wine and a picnic of cold cuts, cheese, and bread, then return by bike. Alessandra and Veronica are among the guides who have led this route.

“What a great way to see Florence on arrival. Alessandra was so friendly and helpful, I loved that her family grew up in the area. Thank you so much.”

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