Tour Tuscany from Florence to Siena

  • Duration 8 Days / 7 Nights
  • Grade
  • Start / Finish Florence / Siena
  • Distance 78 km / 48 miles
  • Trip Style Self Guided
  • Availability
  • Availability
    April - October
  • Price From $1,467


Don't miss the magical landscapes of Tuscany from Florence, the birthplace of the Renaissance, to Siena, a medieval city and a UNESCO World Heritage Site. During this extraordinary walking holiday, you can discover the Chianti region among peaceful forests, vineyards, valleys, villages and farms. 

An unforgettable trip through the wonderful city of Florence where you can see Michelangelo's David and the stunning Duomo. In addition, at the end of your walks you can try the world famous Chianti wines.  

  • Discover the wonderful cities of Florence and Siena.
  • Walk through the Chianti region of Tuscany and explore among quiet forests and villages. 
  • Taste the world-class wines of the region. 
  • Walk paths amongst vineyards, olive groves and cypress trees. 
  • Walk through medieval Siena, a true open-air museum. 

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    • Accommodation
    • Breakfasts
    • Baggage transfer service
    • Transfers specified in the itinerary
    • Information dossier with maps and routes


    • Travel insurance
    • Cancellation insurance
    • Additional nights before, during or after the tour.


    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 Florence you can take a flight to Pisa, Rome or directly to Florence, although there are fewer flights available. From Florence Airport it takes only 15 minutes to reach the city centre by train or bus. 

    If you come from Pisa Airport, you can take a transfer to Pisa Centrale station and there, take a train that takes 1h 15m to Florence. 

    From Rome Airport you can take a Leonardo Express train to the city centre and then a train to Florence that takes approximately 2 hours. 

    When you finish your trip in Siena you can take a train to Florence or Pisa Centrale station and then take another transfer to the airport. 

    You can also go to Rome, only it is a little more complicated, as you must take a train to Florence and then another train to Rome. Trains depart very often and the journey takes 3 h 30 min, depending on the number of stops. Once you arrive in the centre of Rome you can take the Leonardo Express train to Rome Fiumicino Airport.

    On the TrenItalia website, you can check the current timetables.


    This route is classified as moderate because the terrain has rugged areas. It is recommended to be in good shape to enjoy it fully.

    It is an extremely popular region so we suggest you book as soon as you are sure of your dates. Between July 2nd and August 16th, the Palio de Siena Festival is held in the city, making availability very difficult.

    We recommend wearing comfortable clothing, including hats and gloves. In addition to a backpack for daily tours and shoes or walking boots, ideally waterproof. 

    In our information dossier, you will find a detailed list of everything you should carry. 

    If you prefer to do this trip in a slightly cooler climate, we recommend the months of May, June, September and October, where you can enjoy the vibrant colours of Tuscany. 

    July and August can be very hot, so if you decide to go on these dates, it is best to start walking early.

    The airports of Florence, Pisa and Rome are the most convenient to fly both nationally and internationally. Most destinations have a central train station for arrival and departure.

    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).

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    Trust Orbis Ways!

    karen L.karen L. ★★★★★ 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.John W.John W. ★★★★★ 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.Juliana M.Juliana M. ★★★★★ 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!!!Lauren G.Lauren G. ★★★★★ 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%.sanda S.sanda S. ★★★★★ 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.Karin B.Karin B. ★★★★★ 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!Julie F.Julie F. ★★★★★ 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!!js_loader