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: $4,095Dates:  2025
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    2025
    • Apr 21 – 24
    • Apr 28 – May 1
    • May 5 – 8
    • May 12 – 15
    • May 20 – 23
    • May 27 – 30
    • Jun 2 – 5
    • Jun 9 – 12
    • Jun 16 – 19
    • Jun 24 – 27
    • Jun 30 – Jul 3
    • Jul 7 – 10
    • Jul 14 – 17
    • Aug 4 – 7
    • Aug 11 – 14
    • Sep 1 – 4
    • Sep 8 – 11
    • Sep 15 – 18
    • Sep 22 – 25
    • Sep 29 – Oct 2
    • Oct 6 – 9
    • Oct 13 – 16
    • Oct 20 – 23

    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:  2025
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    2025
    • Apr 20 – 25
    • Apr 27 – May 2
    • May 4 – 9
    • May 11 – 16
    • May 18 – 23
    • May 25 – 30
    • Jun 8 – 13
    • Jun 15 – 20
    • Jun 22 – 27
    • Jun 29 – Jul 4
    • Jul 6 – 11
    • Jul 20 – 25
    • Aug 3 – 8
    • Aug 17 – 22
    • Aug 31 – Sep 5
    • Sep 7 – 12
    • Sep 14 – 19
    • Sep 21 – 26
    • Sep 28 – Oct 3
    • Oct 12 – 17
    • Oct 19 – 24

    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: $5,595Dates:  2025
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    2025
    • Jun 15 – 21
    • Sep 21 – 27
    • Sep 28 – Oct 4

    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

  • Tuscany Harvest Bike Tour

    Olives, Truffles, Porcini, Chestnuts... And a Nice Chianti
    Duration: 6 daysLevel: 3Price From: $6,395Dates:  2025
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    2025
    • Oct 12 – 17
    • Oct 19 – 24

    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

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