10 Cycling and Wine Tours in Florence Worth Flying For

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

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

Cycle through Chianti from Florence with scenic country roads, castle wine tasting, olive oil, lunch, guides, and e-bike support.

“I highly recommend this tour especially if you want to get out of Florence and explore the countryside without going too far away. I am a solo traveler and I felt comfortable. If you’re like me and need to know all the details before you do something, here is the breakdown: You meet your guide at their storefront. Use the bathroom at a nearby cafe before leaving! Then you walk to a parking lot and get in a sprinter van and drive to the castle. The ride isn’t too long but it’s beautiful. It’s a very windy road! At the castle you’re given a bike, helmet, water, and some safety…”

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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

Ride an e-bike from Florence to Fiesole and a Tuscan vineyard, with wine, countryside views, GPS guidance, and flexible self-paced travel.

“This was brilliant. Easy to follow and exceptionally beautiful route. The bikes give as mush assistance as you want and worked well. Lovely accommodating host who gives a great explanation of everything to expect on bike ride.”

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

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

Ride from Florence into Chianti on an e-bike, with vineyard views, a winery lunch, two wine tastings, and practical tips for a full-day outing.

“What a wonderful tour this was! Francesco was great as the tour guide and Oscar was just fantastic 👏 I'm sure I was the most inexperienced rider of the tour and if it wasn't for Oscar's encouragement, and the rest of the team, I'm not sure I could have made it up those initial hills 😊 I had the best day ever. The tour of the winery and the lunch that followed was fabulous. I can highly recommend this tour. Thank you for a wonderful day 😊👏”

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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

Review of Florence’s Tuscany bike tour with four hills, Chianti wine, olive oil, Tuscan food, villas, and wide city views.

“Great guide with informative stops and picture-taking. Tuscany countryside ride was beautiful, but was preceded/followed by city ride from/to the bike shop. City ride was a bit treacherous trying to dodge vehicles and people. E-bikes (and introductory instruction) worked well, though many folks did just as well without them. Tastings were little more than a glass of wine and olive oil served with a plentiful Italian lunch plate at a restaurant on the edge of town. Meeting point was difficult to find without a business logo to see from the street. This was probably an ideal half-day bike tour, but for more Tuscany countryside and less city riding I would…”

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5.Tuscany Bike Tour with Wine & Olive Oil

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

Escape Florence by bike for Tuscan hills, San Miniato views, Chianti wine, olive oil, bread, and local cold cuts.

“Very good. Nice way to spend a few hours. Definitely pay extra for e-bikes as the hills would be challenging for any athletic person in the heat of Florence. Would recommend!!”

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

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

Ride from Florence into Chianti on an e-bike, with quiet roads, a family winery, olive oil tasting, and a generous Tuscan lunch.

“The ride is fantastic. In a few short minutes you are outside of Florence and in the hills overlooking the city. The view is breathtaking. The roughly 40km ride was gently paced and easy due to the e-bikes. Our farm/vineyard visit was completely amazing. The history, passion, food, and wine were delivered expertly and enjoyably. Definitely recommend while in Florence.”

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

★★★★★★★★★★4.9 · 18 reviews · from $73

Ride Tuscany’s Chianti hills, enjoy a farm lunch, taste local wine and olive oil, and get practical advice on fitness, hills, bikes, and value.

“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

Ride from Florence into Chianti on an e-bike, with Tuscan views, a farm lunch, and biological wine tasting in a small group.

“Dimitri was a wonderful guide, we saw lovely Tuscan scenery, Dimitri was very knowledgeable and guided us well.”

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

★★★★★★★★★★4.9 · 15 reviews

Ride from Florence into Tuscany by e-bike, stopping at San Miniato and a family winery for wine, olive oil, and local snacks.

“Beautiful countryside! Our guide Totò was very informative and friendly.”

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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 Florence at sunset with wine, Tuscan snacks, Arno views, and local guides through San Frediano, Santo Spirito, and Santa Croce.

“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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