Walking the Hill Towns of Tuscany in 8 days

  • Duration 8 Days / 7 Nights
  • Grade
  • Start / Finish Montepulciano / Siena
  • Distance 90 km / 56 miles
  • Trip Style Self Guided
  • Availability
  • Availability
    March - October
  • Price From $1,881


Take a holiday among the hills, olive trees and vineyards of southern Tuscany, one of the most beautiful regions in Italy.

Discover towns full of history, culture and architectural value, among which are: Montepulciano, Pienza, Bagno Vignoni, Montalcino and Siena.

In addition, you will get to know the wine regions of southern Siena along the paths during this holiday through Tuscany. Enjoy your walks while, through beautiful landscapes and delicious flavours, you have a completely Italian experience.

  • Get to know the ancient Abbey of Sant'Antimo, an Italian architectural
  • Bath in the famous hot springs in Bagno Vignoni.
  • Tour charming medieval and Renaissance-era towns.
  • Taste and accompany your trip with excellent wines.

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    • Accommodation in en suite rooms in charming hotels
    • Daily Breakfasts
    • Luggage transfers between accommodations
    • Transfers as specified in the itinerary
    • 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

    From Siena you can take the train to one of the three nearest airports, located in Pisa, Florence or Rome.

    The length of the journey, depending on the city you are going to, will last from one to two hours.



    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 you make the reservation as soon as possible, as soon as you have decided your travel dates, as Tuscany is an extremely popular destination, especially in the months of July and August.

    The spring season and the months of April, May and June are absolutely lovely.

    Autumn is a perfect time of year, as the landscape is formed by a palette of gold and red colours, so September and October are unmissable.

    July and August can become very hot, so we recommend that you start your walks early to avoid the heat of the day. The towns and cities you will visit are always busy, so you can take your holiday at the time you prefer best.

    We recommend the airports in Pisa, Florence or Rome. You will be able to start and end your holiday with a train journey of one or two hours.

    This tour has a moderate degree of difficulty, with daily walks of between 3 and 7 hours, so you must have an active lifestyle with a good level of physical activity.

    If you choose not to take any of the walks, you can use taxis or public transport to move to your accommodation in the next stage.

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    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!!