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Hiking Tours in Tuscany

Tuscany hiking tours wind through the Chianti hills between hilltop towns - Siena, San Gimignano and Volterra - with vineyards and cypress-lined roads at every turn. Macs Adventure is a leader in self-guided travel, running Tuscany trips for years.

Walk sections of the historic Via Francigena pilgrim route, spend nights in family-run agriturismi, or focus your trip on the Val d'Orcia's UNESCO-listed landscape. Combine with our Cinque Terre or Umbria itineraries for a longer Italian trip.

20+ years of self-guided expertise, hand-picked Tuscan accommodation, and luggage transfers throughout - Macs Adventure is a leader in self-guided travel.

6 routes

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Routes in Tuscany

  • Italy · Switzerland

    Via Francigena

    • Walking
    • 8–50 days
    • Easy - Moderate to Moderate - Challenging
    from$2,540CAD pp
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  • Italy

    Hill Towns of Tuscany

    • Walking
    • 8 days
    • Easy - Moderate
    from$3,050CAD pp
    View Route
  • Italy

    Classic Tuscany

    • Walking
    • 5 days
    • Moderate
    from$1,685CAD pp
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  • Italy

    Classic Chianti

    • Walking
    • 5–8 days
    • Easy - Moderate
    from$2,165CAD pp
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  • Italy

    Trails of Tuscany & Umbria

    • Walking
    • 10 days
    • Easy - Moderate
    from$3,720CAD pp
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  • Italy

    Relaxed Trails of Tuscany

    • Walking
    • 7 days
    • Easy - Moderate
    from$2,325CAD pp
    View Route

Here's why Tuscany remains one of Italy's most-loved hiking destinations:

  • Hilltop towns like Siena, San Gimignano and Volterra break up each day's walking with genuine Renaissance architecture
  • Sections of the Via Francigena, the historic pilgrim route to Rome, run through the Tuscan countryside
  • The Val d'Orcia, a UNESCO World Heritage landscape, delivers the classic cypress-and-vineyard view of Tuscany
  • Agriturismo stays put you in working farmhouses, often with dinner from the estate's own produce
  • Graded Easy-Moderate to Moderate, with rolling hills rather than high-mountain ascent
Walking towards medieval hilltop towns

Tuscany like a local

  • When to go

    April to June and September to October are the sweet spots - mild temperatures and manageable crowds. July and August can be hot for daytime hiking.

  • What the trail is actually like

    Rolling farmland and vineyard paths connecting hilltop towns, with steady but moderate ascent and descent rather than sustained climbing.

  • Where you stay

    Family-run agriturismi and small hotels in or near hilltop towns, chosen for character and easy access to the trail.

  • Fitness needed

    Moderate fitness for rolling hills over multiple days. Tuscany suits most regular hikers, including relative beginners on shorter itineraries.

  • Local food to try

    Tuscan classics like ribollita, pici pasta, and Chianti wine, often served at agriturismi using produce grown on-site.

More regions to explore

Know before you go

Get inspired for Tuscany

  • Hiking

    The Ultimate Guide to Hiking in Tuscany

    Read our Ultimate Guide to Hiking in Tuscany and explore Tuscany's best hiking trails with scenic views, top travel tips, and ultimate dining recommendations.

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    Biking

    Things to do in Tuscany

    Discover the best things to do in the enchanting region of Tuscany. Explore rolling hills, medieval towns, and indulge in rich history and delicious cuisine.

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  • four people wearing aprons learning to make gnocchi

    Biking

    Savor Every Step and Sip in Tuscany

    Discover the best food and drink in Tuscany in our guide that invites food enthusiasts and travel lovers to try the best food and drink when touring Tuscany.

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