Chianti Classic Walking Holiday (Tuscany)

  • Duration 11 Days / 10 Nights
  • Grade
  • Start / Finish Volterra / San Gimignano
  • Distance 71 km / 44 miles
  • Trip Style Self Guided
  • Availability
  • Availability
    April - October
  • Price From $2,153


Between Volterra and San Gimignano you will find timeless landscapes and feel as if you are travelling back in time while discovering dreamy villages, vineyards and wonderful views of sunflower fields. 

The tour starts in Volterra, a walled town from where you can walk through the green Berignone Forest and enjoy the panoramic views before reaching Casole d'Elsa. 

Everything leads to San Gimignano, known as "the Manhattan of medieval Tuscany", which houses a landscape dominated by the vineyards. Take advantage of some of its excellent wines and accompany it with a bruschetta (toasted bread with garlic, olive oil and tomato) or some of the traditional regional pastas.

  • Marvel at the Italian landscapes between sunflower fields and vineyards.
  • Walk on Etruscan paths and pilgrimage routes. 
  • Enjoy the warm welcome of the locals and soak up their culture.
  • Taste the traditional local food and the famous Chianti wines.

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    • Accommodation in hotels and cottages
    • Breakfasts 
    • Evening meals on days 1, 4, 5 and 10
    • Baggage transfers service between accommodation
    • Information dossier with maps and routes
    • 24-hour telephone support
    • Taxes included


    • Unspecified transfers
    • Unspecified meals
    • Drinks and snacks
    • Personal equipment
    • Tourist taxes


    • Travel insurance
    • Cancellation insurance
    • Additional nights before, during or after the tour.
    • Improved hotel room upgrades (if available).


    General information

    The accommodations with which we collaborate have a private bathroom and all the necessary services to ensure the best comfort available.

    Our team checks in situ the quality of all the accommodations offered, so that you have an unforgettable experience during your trip.

    The accommodation that we will book for your trip will be selected taking into account our commitment to you: guaranteeing comfort, calm and enjoyment throughout your trip.

    We work with quality hotels and country cottages with limited capacity, so we invite you to confirm your reservation as soon as possible.

    The name of each accommodation will be provided to you a few weeks before your trip begins.

    Room types

    It is possible to book this journey in single, double or triple rooms.

    All rooms have private bathrooms.


    Travel & Transfers

    To start this route, we will pick you up at Pisa Airport to take you to the hotel, located on the outskirts of the walled town of Volterra. 

    When you finish your trip, you have the option to enjoy extra days in nearby places like Florence (1 hour) or Siena (30 minutes) that you can reach by bus. You can also add extra nights in Volterra to get to know this area better.  


    The best time to tour this region is the month of September. We also recommend doing it in spring, as you will be able to see many flowers and enjoy the pleasant climate of the Chianti region. 

    We recommend that you book as soon as you are sure about your dates, as accommodation can fill up very quickly in this area.

    This journey has a moderate degree of difficulty, so you should have an active lifestyle with a good level of physical activity.

    Once you make your reservation we will send you all the detailed information about the specific equipment you need for this route, considering recommendations for shoes, boots, clothes and a day-to day backpack.  

    Yes, it's included. We will transfer the luggage between each accommodation according to your itinerary. Each person can take a suitcase up to 20 kg (45 lbs).