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Cycling Tours in Tuscany

Tuscany's hill towns and vineyard roads are some of the most photographed cycling terrain in Italy, and two routes cover it well. Cycling Tuscany Chianti & Siena Self Guided Tour loops through Chianti's wine country toward Siena, while Cycling Tuscany: Florence to Montepulciano rides point to point across the region. You can also cycle a section of the famed Via Francigena, starting out in Tuscany’s Lucca and ending in Rome.

All trips include breakfast, daily luggage transfers and route notes in our app, with towns, farmhouses, and sights spaced out so you can stop when something catches your eye.

4 routes

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Routes in Tuscany

  • Italy

    Cycling Tuscany: Chianti & Siena

    • Cycling
    • 8 days
    • Moderate
    from$3,115CAD pp
    View Route
  • Italy

    Wine Trails of Umbria By Bike

    • Cycling
    • 8 days
    • Easy - Moderate
    from$3,510CAD pp
    View Route
  • Italy

    Cycling Tuscany: Florence to Montepulciano

    • Cycling
    • 8 days
    • Moderate - Challenging
    from$4,000CAD pp
    View Route
  • Italy

    Biking the Via Francigena: Lucca to Rome

    • Cycling
    • 11 days
    • Moderate
    from$5,035CAD pp
    View Route

Cycle the rolling hills and cypress tree lined country lanes of Tuscany at your own pace

  • No set groups, guides, or support vehicles, just you and the road
  • Luggage transfers between hotels each day, so you ride light
  • Turn by turn route notes and mapping loaded in the app
  • 24/7 support from our team if plans change
  • Flexible start dates, so you choose when to go
  • Pedal between vineyards, wine cellars, abbeys and Tuscan villages

Tuscany like a local

  • Which Tuscany route has more climbing

    Cycling Tuscany Chianti & Siena covers more of the classic rolling Chianti hills, while Florence to Montepulciano has flatter valley sections mixed in

  • How long are these Tuscany trips

    Both typically run about a week, with daily rides between towns and a rest day option and Biking the Via Francigena around 11 days.

  • Do the routes include wine tastings

    Wine tastings are not included, but two of our itineraries build in stops at vineyards and cellars along the way and you can arrange these for yourself.

  • Is Tuscany a good region for a first cycling trip

    It can be, especially if you choose an e-bike upgrade to manage the rolling hills more comfortably

  • What's the accommodation like

    A mix of farmhouses, small hotels, and boutique properties set among the vineyards and hill towns

More regions to explore

  • Cycling Tours: Verona to Lake Garda & Venice to Porec

    View 1 route

Know before you go

Get inspired for Tuscany

  • Biking

    14 Essential Facts about Biking Vacations

    Read our blog post, 14 Essential Facts about self-guided biking vacations. Macs Adventure are biking vacation specialists - get more insight here.

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  • Biking

    E-Biking - Allowing Everyone To Experience The Joy of Biking

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  • Biking

    Essential Gear to Pack on Your Next Bike Tour

    Discover essential gear for your next bike tour with this ultimate packing list. From clothing to safety equipment, ensure you're fully prepared for an incredible biking self-guided biking vacation.

    Read blog