Discover the best of Tuscany in 5 days

  • Duration 5 Days / 4 Nights
  • Grade
  • Start / Finish Volterra / Siena
  • Distance 69 km / 43 miles
  • Trip Style Self Guided
  • Availability
  • Availability
    April - October
  • Price From $791


In a short but nurtured tour, you can discover the beauty of the Tuscan region and its exquisite gastronomy. You will walk through the ancient and charming towns of Volterra, San Gimignano, Colle di Val D'Elsa and Siena. You will enjoy the incredible view of the green hills, vineyards and Etruscan olive groves.

  • You'll walk through cobblestoned streets, medieval, Romanesque and Gothic churches and palaces.
  • You will delight in the best of Tuscan cuisine.
  • You will taste traditional drinks such as Chianti or Vernaccia.
  • You will discover forests, vineyards and incredible medieval villages.

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    • Accommodation in hotels and cottages
    • Breakfasts
    • Transfers on days 1, 2 and 4
    • Baggage transfer service between stages
    • 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
    • Extra nights
    • Improved hotel room upgrades (if available)
    • Transport from Pisa/Florence/Rome


    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 get to the starting point of this walking holiday in Tuscany, the best option is to take a flight to Florence or Pisa Airport.

    From there, you can go by train to Pontedera Station (approximately 45 minutes from Florence and 15 minutes from Pisa) or Poggibonsi (1h 15m from Pisa or Florence).

    From Pontedera or Poggibonsi Station, you will have a transfer included to your first accommodation in Volterra.

    When you finish your trip, from Siena you can head by train to Pisa (1h 45m), Florence (1h 30m) or Rome (3hrs). You can visit the Trenitalia website for options.


    If you prefer to walk in a less hot season, May, September and October will be ideal. In addition, in autumn, the colours in Tuscany are spectacular.

    Temperatures in June, July and August can be very high.

    We suggest you book once you have decided your plans, as the Tuscany region is very popular and room reservations should be made as soon as possible.

    We will do our best to live up to your expectations.

    We recommend you to be in good physical condition to make the most of this holiday.

    This route has a medium-high level of difficulty, as the terrain is mountainous. The vast majority of the paths are rural and on gravel.

    Daily walks range from 17 km to 25.5 km (10.5 to 15.8 miles) and walks are optional on two days of the itinerary.

    You also have the possibility to skip a walk between cities. You only have to notify us in time so that you can make the trip by taxi.

    With advance notice, you can take the taxi that transfers your luggage and thus avoid walking between hotels.

    You can also use public transport or local taxis to continue on to the next property.

    There are three days when the walks are from one hotel to another, but on the other days the walks are optional, so you can choose between exploring on foot or just relaxing.

    Yes, this is a requirement to book with us. It's important that this insurance covers your activities, emergency evacuation, and hospital care.

    You will need good walking shoes or boots, comfortable clothes, waterproof jacket and pants, a backpack, gloves/hats, etc.

    The full list will be given to you once you book your trip.

    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).