13 Cycling and Wine Tours in Italy to Build a Day Around

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

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

Start with John at E-Bikes Florence, then follow a GPS route from Florence through Fiesole, olive groves, forest, and country roads to a boutique vineyard. You control the pace, stops, and time, with roadside help available. Expect hills, city traffic, and a rewarding wine and picnic stop.

“This is for people comfortable on an ebike and biking on roads. You also need to be comfortable following a GOS map while biking. Given all that… this was probably our favorite activity in Florence! It was great to get into the country side and we loved going at our own pace and stopping wherever we wanted! The views were amazing. The winery was wonderful with some of the best food we had while in Florence! If you like to tour by bike you will love this!!!”

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2.Naples Scenic E-Bike Ride to a Local Vineyard with Meal

★★★★★★★★★★5.0 · 288 reviews · 4 hours (approx.) · from $95

Ride a pedal-assisted e-bike from Naples into the Phlegraean Fields with guides such as Alessandro, Max, or Guido. Stop at Roman ruins, volcanic sites, and Lake Averno before tasting family-made wines with local food at a vineyard. Pickup across Naples is available.

“This was an excellent experience. The ebikes make it easy to pedal along taking in the sights of your surroundings as we made our way to the vineyard. And the vineyard was delightful! Alexander gave us a great experience as we biked to and from the vineyard sharing history of the surroundings. Most excellent!”

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3.Tuscany Bike Tour with Wine & Olive Oil

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

Ride 11 km through Florence’s southern hills with a local English or Italian-speaking guide, passing villas and olive groves before a family-run tasting of Chianti, olive oil, bread, cheeses, and cold cuts. Regular bikes suit active riders; e-bikes cost €20 extra and are limited.

“Gabriella was great-- their passion for Italian history really came through and made us want to learn more. 😎🤌🙌”

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4.Lucca: Guided E-Bike and Wine Tour

★★★★★★★★★★4.8 · 148 reviews · from $123

Ride with guides such as Luca, Marta, Sara, or Chiara around Lucca’s walls and into the nearby countryside. After a few easy climbs by e-bike, visit a family winery for wine, olive oil, bruschetta, cheese, and cold cuts, with time to learn how the wine is made.

“Chiara was a wonderful guide. She was extremely knowledgeable of the area and gave us a great insight into Lucca, its history and surrounds. Lunch at the winery was delicious with a spectacular view. I would highly recommend this tour”

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5.Scenic E-Bike Ride with Vineyard Wine & Meal

★★★★★★★★★★4.7 · 67 reviews · 5 hours · from $93

Ride an e-bike from Naples along Pozzuoli’s coast and into the Phlegrean Fields with guides such as Alessandro, Tino, or Barbara. Stop at volcanic Lake Averno, Roman ruins, and a vineyard for organic food, cheese, honey, and local wine. Expect some busy city roads.

“Great guide, very nice landscape and good food and wine at the winery. All in all a grest experience.”

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6.Umbria E-Bike & Wine Tour through Vineyards and Olive Groves

★★★★★★★★★★5.0 · 53 reviews · 6 hours (approx.) · from $205

Ride a Bianchi trekking e-bike through Bevagna, Cannara, vineyards, and olive groves with a professional guide. The six-hour outing includes a 10-kilometer greenway ride, coffee stop, organic winery tasting, homemade lunch, water, helmet, and optional paid pickup.

“Danielle was the perfect tour guide. Nice tour and exceptional food and wine at the winery. I can highly recommend this tour for the whole family.”

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7.Spello E-Bike & Wine Tour with Scenic Winery Lunch

★★★★★★★★★★5.0 · 27 reviews · 6 hours (approx.) · from $216

Join Daniele, Laura, or their small team for a six-hour e-bike ride from Torre del Colle through Spello’s countryside and the ancient Olive Path to Assisi. Stop for coffee, views, organic wine, olive oil, and homemade pasta at Tili Vini. Pickup is available for an extra fee.

“My husband and I love bike riding and this was a PERFECT day for us! Daniele and Laura were the most gracious and wonderful guides and we met an amazing group of people on our ride! Thank you for an incredible and memorable day!”

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8.Montecatini Terme cycle and wine tasting visit

★★★★★★★★★★5.0 · 19 reviews · 5 hours (approx.) · from $204

Ride through Tuscan orchards, vineyards, and quiet country roads with guide Massimo or Marco, stopping in Montecarlo and Fattoria Il Poggio. The private five-hour tour suits confident cyclists, with e-bikes available for an extra €30. Wine, lunch, and alcohol cost extra.

“It was a great way to see Tuscany that didn't involve sitting on a bus. It was a bit scary riding a bike with traffic but the drivers were cognizant and Massimo, our guide, made sure we were safe. I would highly recommend this excursion. Be sure you can handle uphill pedaling. The wine tour was great as well.”

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9.Bike Ride & WIne Tasting

★★★★★★★★★★5.0 · 7 reviews · 3 hours (approx.) · from $144

Leave Lucca by bicycle with guide Alessandro and ride into the countryside around Mutigliano. At Azienda Agricola Valle del Sole, stroll among the vines, taste four wines and local olive oil, and enjoy a snack. Bring or rent a bike, since bicycle hire costs extra.

“I went on a 30-kilometer bike tour with Alessandro around Luca, and we made a stop at a winery. I definitely recommend it—it's totally worth it!”

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10.Assisi to Spello Bike & Wine Tour

★★★★★★★★★★4.0 · 4 reviews · 3 hours · from $106

You’ll ride from Assisi to Spello along the Via degli Ulivi, using an e-bike and GPS route rather than a standard guided tour. Stop for Umbrian wine, bruschetta, and organic olive oil, then return past Rivotorto and Santa Maria degli Angeli. Daniele has guided some departures.

“Our bike tour was great. Our guide Daniele was was very helpful to show us the way and explain where we were. Our wine tasting host was very informative and the wine and meat and cheese was very good.”

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11.Gioia del Colle: Primitivo Wine & E-Bike Ride

★★★★★★★★★★5.0 · 4 reviews · 2 - 3 hours · from $81Best value

Cycle 25 to 30 km through Gioia del Colle’s vineyards, olive groves, dry-stone walls, and rural roads on a premium e-bike. Your English or Italian tour leader stops at the Stele of Primitivo Wine, with an optional tasting or vineyard toast, including wine and appetizers with Roberto on selected options.

“I need to start by saying that I am not very good at riding a bike and deciding to take this tour was a risk-based decision. That being said, I enjoyed the experience overall, although I would have appreciated a little bit more of a guided tour instead of just riding around. I also know that the guide adapted the route for my needs, so this may also be my fault. The wine and appetizers with Roberto at the end were amazing and definitely the highlight of the day!”

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12.Enjoy a Wine Tasting after a cycling excursion in the magic of Tuscany

★★★★★★★★★★5.0 · 4 reviews · 4 hours (approx.) · from $164

Set out from Podere Casanova near Montepulciano for a small-group bicycle ride through Tuscan vineyards with guide Andrea. After about 1.5 hours on the road, return to the winery for a look at winemaking, regional wines, and a generous menu of pasta, cheeses, cured meats, and dessert. Standard bikes are included, with e-bikes available for €20.

“A beautiful bike ride through through the Tuscan hills with our friendly guide Andrea followed by the most delicious lunch and wine tasting at Podere Casonova.”

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13.Guided Cycle Tourism Wine Tour by E-Bike on the Island of Elba “Arrighi”

★★★★★★★★★★5.0 · 3 reviews · from $98

Ride an e-bike through eastern Elba with guides Alessia and Rosario, stopping at Rio nell’Elba, Terranera Beach, Porto Azzurro, and Arrighi’s 13-hectare vineyards. Antonio Arrighi leads a tasting of five island wines and extra virgin olive oil. The small group is limited to eight people.

“La rencontre avec Alessia et Rosario, nos guides, et avec Antonio, propriétaire de l’azienda agricola, nous laissera un magnifique souvenir. Leur enthousiasme, la beauté des paysages, la dégustation exquise du vin et de l’huile d’olive fut très apprécié. A recommander vivement”

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