Walk the best of Tuscany in 8 days

  • Duration 8 Days / 7 Nights
  • Grade
  • Start / Finish Volterra / Siena
  • Distance 101 km / 63 miles
  • Trip Style Self Guided
  • Availability
  • Availability
    April - October
  • Price From $1,531


Explore the best of Tuscany as you tour Volterra, San Gimignano, Colle Val D'Elsa Monteriggioni and Siena. Live a unique and enriching experience in one of the most important Italian regions for its historical, artistic and cultural value.

On this holiday, you will discover landscapes with paths of ascents and gentle descents among amazing villages located in the middle of green meadows and incredible vineyards that will lead you to experience the medieval and Renaissance essence and Gothic architecture.

Delight in the best local organic food accompanied by the best pecorino cheese, artisan pasta, sweet wine, saffron dessert and an innumerable offer of gastronomic delights on offer in this region.

  • Get to know the essence of classic medieval style.
  • Taste a wide range of excellent wines from this region.
  • Get to know and enjoy the best local organic food.
  • Explore the wonders of Volterra, San Gimignano, Colle Val D'Elsa and Siena.

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    • Accommodation in en suite rooms in charming hotels
    • Daily Breakfasts
    • Luggage transfers between accommodations
    • Transfers as specified in the itinerary (Days 1, 2, 3 and 6)
    • Information dossier with maps and routes
    • 24-hour telephone support
    • Sustainable travel, we compensate the CO2 emissions of your trip
    • Taxes


    • Travel insurance
    • Cancellation insurance
    • Additional nights


    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 your holiday, we recommend that you arrive at Florence or Pisa Airport and take a train to Pontedera or Poggibonsi.

    A taxi will be waiting for you and will take you from the train station of the city you have chosen to Volterra.

    When you finish your holiday, you can go by train to Pisa or Florence so you can take the flight back to your home city.


    Absolutely! Each traveller has included 1 piece of luggage that we will transfer between your accommodations. It's important that this piece of luggage meets the following criterias:

    • Maximum weight of 45 lbs (20 kg).
    • Must be only 1 piece of luggage without any attachments or accessories.
    • Should not contain valuables, fragile items, food or medications.
    • Must be correctly identified (booking reference of your trip and the full name of the trip holder).

    The approximate luggage delivery time will be at 4:00 PM.

    We suggest that you make the reservation as soon as possible, as soon as you have decided the dates of your holiday, since Tuscany is a highly sought after and popular destination. 

    If you prefer to hike in cooler seasons, May, September and October are perfect.

    Although in autumn Tuscany is dressed in beautiful and unique colours, in summer you can also travel, but temperatures can be very high on these dates. 

    On this holiday, you will have walks between 17 km and 25.5 km each day, so you must have an active lifestyle with a very good level of physical endurance.

    If you decide not to take any of the walks, remember that with advance notice you can travel in the taxi that transports your luggage between accommodation. 

    The most important thing is that you bring everything you need to make your holiday comfortable. For example, waterproof boots, instead of shoes, as they will give you better support during the walk; light clothing and a backpack to carry during the day with a cap, sunglasses and sunscreen.

    If you cannot do one of the stages, we can transfer you in the same taxi that carries your baggage between accommodation and avoid those walks, provided that you notify us in advance. Also remember that you have days off where you can choose short routes or relax.

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    Trust Orbis Ways!

    Orbis Ways
    Based on 129 reviews
    The administration was good before our trip and our questions were answered quickly. The accommodation was also good. We had no problems with the baggage transfer too.
    Our group of 5 had a really great experience with orbis ways. Our contact person was helpful via email and via phone. Great accommodations and each host was helpful and generous with kindness.
    I travelled last week to Madeira with Orbis Ways and it has been an amazing experience. Accommodations were exceptional, and everything was explained very well, apart from that the Island is amazing, must be seen at least once in a lifetime. Dinners were very good, with local fresh homemade food! Very recomending!!!
    Excellent trip. Excellent communication with Orbis. Lovely accommodations. Luggage transfer was always done well and the overall trip was excellent. I cannot wait to do another walk in 2023 and will use Orbis ways 100%.
    Few days ago I finished Camino Francés. Orbis Ways planned the trip for me, arranged my routes and accommodations as well as luggage transfers. Everything went smoothly from the beginning in St Jean Pied du Port until the end in Santiago. Rooms with private bathrooms that they booked for me were comfortable and clean and luggage transfers underwent without mistakes. My daily routes were well planned. In 34 days I had only two problematic situations with accommodations and their 24 hours assistance team solved them in few minutes. I enjoyed every minute of my Way. I am planning to return and do some other route - Norte and Portugués gor sure. Orbis Ways will be my choice again.
    I did the wonderful walking holiday trip of 8 days Mont Blanc...the experience was incredible, from the beginning everything chosen in the dossier was beyond expectations, providing all the necessary information.I am very grateful for the wonderful and detailed attention of Jhonay. Also the accommodations chosen were very comfortable!I have no doubt that I will repeat as soon as I can, the routes are spectacular!
    Orbisways did an outstanding job of planning our trip along the Camino de Santiago. The provided voucher provided excellent information, the accommodations were awesome, never had any confusion regarding travel details and the staff I worked with prior to our trip were kind and very efficient. I highly recommend OrbisWays and will definitely be traveling with them again!!