Tuscany Bike Tours

A Tuscany vacation is what dreams—and movies—are made of. Sandwiched between Liguria and Umbria in Italy’s geographic center, the region’s iconic green and gold landscape alternates with short and steep hills, making it a popular training ground for professional cyclists. The fortifications of hill towns like Siena and San Gimignano tell a long and fascinating history of battles, pilgrimages, plagues, and politics, while Florence, with its seminal art and architecture, is singlehandedly responsible for the rise of the Italian Renaissance.

Eat

Hand-rolled pici pasta, pecorino cheese, olio nuovo (fresh-pressed olive oil), truffles, fava beans, artichokes, chestnuts, porcini mushrooms, Chianina beef, and cinghiale (wild boar)

Drink

World-famous wines made from native Sangiovese grapes including Brunello, Chianti Classico, and Vino Nobile; international blends known as Super Tuscans; and—in classic Italian fashion—espresso and cappuccino

What Locals Love

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  • Classic Tuscany 4-Day Bike Tour

    A Taste of Tuscany: Shorter and Just as Sweet
    Duration: 4 daysLevel: 1Price From: $4,295Dates:  2026
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    2026
    • Apr 13 – 16
    • Apr 20 – 23
    • Apr 27 – 30
    • May 4 – 7
    • May 11 – 14
    • May 18 – 21
    • May 25 – 28
    • Jun 1 – 4
    • Jun 9 – 12
    • Jun 16 – 19
    • Jun 30 – Jul 3
    • Jul 7 – 10
    • Jul 14 – 17
    • Aug 4 – 7
    • Aug 17 – 20
    • Aug 31 – Sep 3
    • Sep 7 – 10
    • Sep 14 – 17
    • Sep 21 – 24
    • Sep 28 – Oct 1
    • Oct 5 – 8
    • Oct 12 – 15
    • Oct 19 – 22
    • Oct 26 – 29

    Any scheduled tour can be made private. Your group, your dates. Go Private

  • Classic Tuscany Bike Tour

    Essential Italy: What Locals Love Beyond Siena and Florence
    Duration: 6 daysLevel: 3Price From: $6,295Dates:  2026
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    2026
    • Apr 12 – 17
    • Apr 19 – 24
    • Apr 26 – May 1
    • May 3 – 8
    • May 10 – 15
    • May 17 – 22
    • May 24 – 29
    • May 31 – Jun 5
    • Jun 7 – 12
    • Jun 14 – 19
    • Jun 15 – 20
    • Jun 21 – 26
    • Jun 28 – Jul 3
    • Jul 5 – 10
    • Jul 12 – 17
    • Jul 26 – 31
    • Aug 9 – 14
    • Aug 23 – 28
    • Aug 30 – Sep 4
    • Sep 6 – 11
    • Sep 13 – 18
    • Sep 20 – 25
    • Sep 27 – Oct 2
    • Oct 4 – 9
    • Oct 11 – 16
    • Oct 18 – 23
    • Oct 25 – 30

    Any scheduled tour can be made private. Your group, your dates. Go Private

  • New Tour

    Colnago Tuscany Bike Tour

    Legends + Luxury: A Colnago World Immersive in Italian Cycling
    Duration: 6 daysLevel: 3Price From: $8,995Dates: Travel dates not yet available. Contact us for details.
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    Travel dates not yet available. Contact us for details.

    Any scheduled tour can be made private. Your group, your dates. Go Private

  • Italian Coast-to-Coast Journey Bike Tour

    From the Adriatic Coast to the Ligurian Sea: Through the Heart of Central Italy
    Duration: 7 daysLevel: 4Price From: $5,995Dates:  2026
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    2026
    • Jun 14 – 20
    • Aug 30 – Sep 5
    • Sep 20 – 26
    • Oct 4 – 10

    Any scheduled tour can be made private. Your group, your dates. Go Private

  • Private only

    Super Tuscany Bike Tour

    An Expression of Italian Life at Its Finest
    Duration: 6 daysLevel: 3Price From: $9,295
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    This tour is for private groups only. There are no scheduled dates. Go Private

  • New Tour

    Tuscany By the Sea Bike Tour

    The Etruscan Coast + Maremma: Bolgheri to Elba Island
    Duration: 6 daysLevel: 3Price From: $6,495Dates:  2026
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    2026
    • May 10 – 15
    • Jun 7 – 12
    • Jun 14 – 19
    • Sep 27 – Oct 2
    • Oct 4 – 9

    Any scheduled tour can be made private. Your group, your dates. Go Private

  • Tuscany Harvest Bike Tour

    Olives, Truffles, Porcini, Chestnuts... And a Nice Chianti
    Duration: 6 daysLevel: 3Price From: $6,695Dates:  2026
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    2026
    • Oct 11 – 16
    • Oct 18 – 23
    • Oct 25 – 30

    Any scheduled tour can be made private. Your group, your dates. Go Private

  • Private only

    Tuscany Villa Bike Tour

    A Private Countryside Ride + Retreat
    Duration: 7 daysLevel: 3Price From: $5,995
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    This tour is for private groups only. There are no scheduled dates. Go Private

See All DuVine Tours