Walk the best of Tuscany in 5 days

  • Duration 5 Days / 4 Nights
  • Grade
  • Start / Finish Volterra / Siena
  • Distance66 km/ 41 miles
  • Trip Style Self Guided
  • Availability
  • Availability
    April - October
  • Price From 954 €

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.




  • Accommodation in en suite rooms in charming hotels
  • Daily Breakfasts
  • Luggage transfers between accommodations
  • Transfers as specified in the itinerary (Days 1, 2 and 4)
  • 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 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 Trenitaliawebsite for options.


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.

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.

Thousands of satisfied customers.
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!!