Classic Tuscany Walking Holiday

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Classic Tuscany Walking Holiday

Distance: 69 km.

Duration: 5 days / 4 nights

Meals: Breakfasts

Accomodation: Hotels

Price: From 580€ per person

Our Official License as a Wholesale Agency (Tour-Operator) allows us to work without intermediaries.

Are you one of those people who dream of a hiking trip tasting the best gastronomy of the area? The classic Tuscany hiking trail is the ideal route for you to get to know stunning landscapes and fall in love with the most famous wines, pastas, oils and cheeses in this area of Italy.

You will enjoy a few days of enchanting hikes starting in Volterra, enjoying all the medieval villages that you will cross and discovering the many vineyards that grant fame in wines to Tuscany.

You will come across San Gimignano, a small walled village of medieval architecture located high in the Tuscan hills, whose historic centre was declared a World Heritage Site by UNESCO in 1990. 

Finally, to reach Siena, your destination on this journey, you will have to go the same way as those pilgrims who travel the famous Via Francigena. At the end of your tour you can continue along the Via Francigena or join another of our Italian hiking routes.

You can enjoy our baggage transfer service that will allow you to walk much easier while discovering the beauty of this hiking trail through the towns and villages you’ll be visiting.

Also, if you have any incidents en route, we are at your disposal 24 hours a day via an emergency telephone. With Santiago Ways, you will walk safely and comfortably.

We’re glad you’ve got this far. Now, we just need to know how you want us to help you prepare your trip. We’re waiting for you! Leave us your details and we will send you a quote tailored to your requirements.


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    Arrival in Volterra

    Today you will arrive in Volterra and, for this, we offer you two options. The first is to arrive by plane to Pisa and, from there, take a train to Pontedera. The second is to arrive by plane to Florence and, from there, go by train to Poggibonsi. From either of these two cities, we can book you a private transfer to Volterra.

    In Volterra you will spend your first night before starting your hiking tour through the Tuscan classics. This small village located in the heart of the Tuscany region is considered a sanctuary of architecture and art from the Etruscan, Roman, Medieval and Renaissance periods.

    Overnight: Etruria Hotel - Volterra


    Hiking to San Gimignano

    To start your day you will have an included transfer that will take you to the Montenero Nature Reserve, specifically to the village of Ulignano, from where you must start walking.

    You will cross forest trails to reach the Castelvecchio Reserve and then find San Donato, the medieval village from where you can see San Gimignano, your destination today.

    Once there, at the highest point of the hill, you will delight in its towers and its Romanesque architecture. In the Tuscan walled villages of medieval times such as San Gimignano, wealthy families competed with each other to have the tallest towers as a symbol of power.

    Today, of the 72 towers it had, little more than a dozen of them are preserved in this small and charming walled village. However, they are considerably more than those preserved in other Italian cities that lost their towers in wars, catastrophes or urban renovations.

    As a curious fact, we tell you that given its location at the top of a hill, during the Middle Ages and the Renaissance, it was an indispensable stopping point for pilgrims of the Via Francigena on their way to Rome.

    Length: 22,5 km. | 325 m. in ascent and 430 m. in descent

    Overnight: Le Unidic Lune Hotel - San Gimignano


    Hiking to Colle di Val D’Elsa

    Today, you must join the pilgrims who are travelling along the Via Francigena, an ancient route that is still preserved today and increasingly takes on prominence among hiking enthusiasts, start from Canterbury, in the south-east of England, to Rome.

    You will walk through vineyards and small villages until you reach the small village of Colle di Val D'Elsa, famous for its historical tradition of glassware. We suggest you take a walk through its craft shops.

    If you complete this route in September, you are likely to coincide with the craftsmen's stalls and the concerts of the LiberaCollaArte Art and Music Fair, which takes place every year at this time.

    Length: 25,5 km. | 320 m. in ascent and 500 m. in descent

    Overnight: Arnolfo Hotel - Colle Di Val D'Elsa


    Hiking to Siena

    Starting your route today you will have an included transfer to Monteriggioni, in the Siena hills . You will start walking again following the pilgrims of the Via Francigena, so the route will be perfectly signposted.

    Once in Siena, your destination today, we suggest you take a walk through this small town located on three hills. Explore its historic centre, which in 1995 was declared a World Heritage Site as the embodiment of a medieval city. Visit its Cathedral, Campo Square and Salimbeni Square.

    Length: 21 km. | 345 m. in ascent and 265 m. in descent

    Overnight: La Chicca Hotel - Sienna


    Return from Siena

    Today you finish your route and you will have to return by train from Siena to Pisa or Florence, depending on where you must take your flight back home.*

    *Remember that when you book your circuit you can ask us to book additional hotel nights for the days after the end of your circuit to extend your stay in one of the municipalities on the Tuscany Classics hiking route.

    End of our services.

    General information 

    All the rooms you will find on this hiking trail have a private bathroom and all the necessary services to ensure good comfort. 

    Our team checks on site the quality of all the accommodation offered in order for all travellers to have an adventure experience always accompanied by nights of absolute rest.


    When working with quality accommodations with limited capacity, the exact name of the location will be provided 30 days before the start of the trip.

    All our accommodation is subject to availability. In case we can't offer you any of them for reasons of capacity, we'll accommodate you in one of equal or better quality.

    Individual rooms

    Single rooms are available subject to availability. Reservations must be made in advance and come at an additional cost.

    Where am I going to stay?

    All our accommodation has been selected to ensure tranquillity, rest and enjoyment along your hiking trail:

    Accomodation in Volterra - Etruria Hotel

    Accomodation in Volterra

    Accomodation in San Gimignano - Le Undici Lune Hotel

    Accomodation in San Gimignano

    Accomodation in Colle di Val D’Elsa - Arnolfo Hotel

    Accomodation in Colle di Val DElsa

    Accomodation in Siena - La Chicca Hotel

    Accomodation in Siena

    Included services

    Accommodation in hotels.

    Rooms with private bathroom.

    Meal plan of your choice.

    Complete itinerary of your trekking route through classic Tuscany.

    Baggage transfer.

    Transfers according to the itinerary on days 2 and 4.

    24 hours Telephone assistance on route.


    Additional services

    Additional single room: to consult.

    Extra nights (breakfast included): to consult.

    Transfer from Pontedera or Poggibonsi to Volterra: to consult.

    Travel assistance insurance: 3€ per person and day.

    Cancellation insurance: 3€ per person and day.

    In order to resolve our travellers' doubts, we answer, to follow, the most frequently asked questions when we receive inquiries about our hiking trails.

    If you have any other questions, you can contact us and we will be happy to help you resolve all your doubts. 



    What is the best time of year to travel on this route?

    This route is available between May and October. The beginning of autumn is the best time to explore the hiking trail through classic Tuscany.

    How do I get to the starting point?

    The best way to get to Pontedera is from Pisa Airport, where you can take a train that takes around 15 minutes. Check the schedules on Trenitalia.

    The best way to get to Poggibonsi is from Florence Airport, where you can take a train that will take around 1 hour and 15 minutes. Also check the schedules on Trenitalia.

    From either of these two cities we can book you a private transfer to Volterra, the starting point of your hiking route through classic Tuscany.

    Once you finish your route you can return from Siena by taking a train to Pisa or Florence, depending on where you must take the return flight.

    Can I travel alone?

    Yes, you can. On most of our hiking trails we offer accommodation in single rooms if the traveller requires it. Single rooms have a special surcharge and are subject to availability.

    Please note that for security reasons, some of the routes are not suitable for solo use.

    This hiking trail is suitable for solo travellers, so you won't have any problems if you're on your own.

    When can I start my trail?

    You can start your hiking trail any day of the year according to the specifications of your itinerary.

    Does this route have an accompanying guide?

    All our hiking trails are completed in self-guided mode. Thus, each traveller has the opportunity to advance on their own and at their own pace for each of the routes marked during the full route itinerary.

    What does the full route itinerary contain?

    The route's complete itinerary is a guide we prepare for you with information on the maps, routes and sights of each hiking route.

    You will receive it by email one month before starting the trip along with all the documentation of the trip: accommodation reservations, luggage transfers, among others.

    The kilometres of travel and the journey times indicated for our hiking trips are reference values.

    It will depend on each walker the fulfilment of these times and distances, according to the speed at which they advance.



    What should I consider to prepare physically?

    Both sedentary people and those who regularly exercise should physically prepare for any of our hiking trails. 

    Sedentary people can start with moderate activity and continue progressively. They should start by taking small 20-minute walks, two or three times a week. It is suggested to increase the time until you reach walk about 4 or 5 kilometres every hour.

    People with regular physical activity can start by walking from 45 to 60 minutes a day and increase the amount of time and kilometres they travel in the same span of time.

    Generally, it is recommended to start training about three months before starting the route. 

    How far in advance should I make the reservation?

    There is no minimum number of days in advance to book, although on certain dates the occupancy of the accommodation is higher, especially in high season. 

    Therefore, in order to guarantee availability in the best accommodation, we suggest you book as much in advance as possible, so that we can meet all your needs. 

    What clothes and hiking equipment are indispensable?

    For any of our routes we suggest you to bring the following items: light and fast drying clothing, waterproof jacket and trousers, sun hat, sunglasses, sunscreen, a pair of shoes suitable for hiking, trekking poles, a pair of shoes to rest in, a jacket that doesn't take up much space and a bottle to carry water.

    Depending on the time of year in which you make the route, these items may vary. 

    Remember that with Santiago Ways, you have included a baggage transfer service between stages, so we will take your backpack from one accommodation to another so that you only worry about walking (maximum 1 piece of 20 kg per person).

    For this reason, we suggest you prepare a second backpack, much smaller, that you can carry with you every day with water, sunscreen, cap, sunglasses, documents, some food and cash. 

    How does the baggage transfer work between stages?

    Every day, at 8:00 am, you must bring your luggage, properly labelled, to the reception. One of our carriers will pick it up and take it to the place where you are going to stay on your next stage.

    Delivery time varies according to the distance between stages and the carrier's delivery route. Usually, delivery is made before 4 p.m.

    Please note that on many routes you sleep more than one night in the same accommodation, so the baggage transfer will not be necessary in these cases.

    Should I take out travel insurance?

    To make any of our hiking trails it is advisable to have travel insurance with all the necessary coverage, especially emergency evacuation and medical care.

    To do this, we suggest you take out the Travel Assistance Insurance and Cancellation Insurance that we offer you in Santiago Ways. If you want more information about it, we will be happy to answer your questions.



    Do all rooms have a private bathroom?

    Yes, all rooms you book for hiking trails with Santiago Ways have a private bathroom.

    Can I sleep alone in a room?

    Yes. We offer accommodation in single rooms and double rooms, according to the requirements of each traveller. 

    Single rooms have a special surcharge and are subject to availability.

    When do you tell me which hotels I'm going to sleep in?

    We work with multiple accommodations in all locations which allows us to guarantee the best quality rooms for our travellers, provided that they are booked well in advance. 

    The name and exact location of each hotel is sent about one month before the start of the trip.

    Am I going to share a room with strangers?

    No. All the accommodations we book for our travellers have private rooms with private bathrooms in order to guarantee all the comfort and comfort they need to rest properly.

    Is the accommodation close to the route I need to follow?

    All the accommodation we book is located in the centre of the villages. In any case, depending on availability, if any accommodation is quite far from the centre, they are all accessible on foot. 

    When necessary, Santiago Ways will offer a transfer to the traveller so that they can reach their accommodation in the most comfortable way possible.

    What kind of accommodation do you book?

    All the accommodation we book in Santiago Ways offer the necessary comfort to rest after long days of walking. We have partnerships with hotels, country houses, mountain retreats and charming farm stays, always with a room and a private bathroom.

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