Cycling Tours

TUSCANY

8 Best Cycling Tours In Siena

Most booked first.

Our shortlist of the 8 most-booked cycling tours around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.

8 Best Cycling Tours In Siena

From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine

From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine - Getting started at Siena Train Station (and why it’s easy)

1.From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine

Most Popular 4.8

E-bike through Chianti from Siena, visit 13th-century Monteriggioni, then enjoy a farm lunch with wine and olive oil.

“We actually ended up doing a tour to an organic winery and visited an Alabaster crafter. Our tour also took us to a couple castles. My husband and I had a wonderful time, we would highly recommend this tour group!!!!”

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Small Group E-Bike Chianti Tour with farm lunch from Siena

Small Group E-Bike Chianti Tour with farm lunch from Siena - Morning ride on the Chiantigiana: 20km of views with real stops

2.Small Group E-Bike Chianti Tour with farm lunch from Siena

5.0

Small-group Chianti e-bike tour from Siena with farm lunch, olive oil tasting, and a winery wine moment on quiet country roads.

“It was all great! Lunch & wine tasting at Oliviera was perfectto, The Bandini were gracious hosts. Our guide, Domenico was helpful, safety conscious and knowledgeable. I highly recommend this tour to anyone with some bicycling experience. If you are not comfortable riding in some traffic this might not be suitable.”

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Chianti Classico E-Bike Tour

Chianti Classico E-Bike Tour - Castello di Brolio: Ricasoli Roots and Castle Views Without the Long Detour

3.Chianti Classico E-Bike Tour

5.0

Chianti Classico by e-bike from Siena: Brolio Castle views, village rides, wine tasting, and a light lunch in about 5–6 hours.

“Seeing Tuscany on an E Bike was the perfect way to see it. We were two people on a private tour. Our guide Ricardo was very helpful and enjoyable to talk to. Our stop at a winery was a delight and we got to be up close and personal with watching them unload grapes from…”

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E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles - Siena to Geggiano: where the ride starts with stories and photos

4.E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

4.5

E-bike through Chianti Classico gravel roads from Siena, with castle stories, a Castello di Brolio tour, and Ricasoli tastings.

“I just completed an unforgettable experience with an ebike tour in Chianti and I can't help but recommend it to anyone looking for a unique adventure, between breathtaking landscapes and local delicacies. The tour included a visit to Castello Ricasoli, one of the historical gems of the region, where we were able to immerse ourselves…”

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Private E-bike Tour in Chianti from San Gimignano

Private E-bike Tour in Chianti from San Gimignano - The 2-Hour Ride on Strada Statale 222 Chiantigiana

Private Ebike Tour in Chianti

Private Ebike Tour in Chianti - Stop 1: The bike and helmet handoff (the part that sets your comfort level)

7.Private Ebike Tour in Chianti

5.0

Private e-bike tour in Chianti from Castellina in Chianti: medieval village walk, vineyard views, and winery lunch with wine tasting.

“This was our favorite excursion of the 6 different ones we did throughout our 10 day Italy trip. Our guide, Samuel, was wonderful and put up with us Americans. The scenery was beautiful. We stopped for lunch at a local farmer’s home where all the food and drink came from their farm, vineyard, and olive…”

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Maremma natural park e-bike tour

Maremma natural park e-bike tour - 30 km on an e-bike: What “easy” feels like in practice

8.Maremma natural park e-bike tour

4.5

Easy guided e-bike loop through Maremma Natural Park from Alberese, with abbey ruins, wild beach picnic, Porte Vinciniane, and sea views.

“Very beautiful landscape surrounded by nature , very beautiful sea and beaches , bike paths surrounded by nature , with my son we did many spectacular bike rides .... RecommendationAuto-translated”

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