Walking Holiday from Florence to Siena

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Walking Holiday from Florence to Siena

Distance: 58 km.

Duration: 8 days / 7 nights

Meals: Breakfasts

Accomodation: Hotels

Price: From 925€ per person

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

Do you want to know the essence of the most charming Italian cities, stroll through their vineyards, get to know their history, and discover the medieval villages that connect them? In the Walking Holiday from Florence to Siena, you will fall in love with the place.

You will start your trip in Florence, one of the most romantic cities in Italy, from where you will begin to tour the multiple Tuscan landscapes, discovering immense olive groves, the vineyards of traditional Chianti wine, as well as lots of oak forests that will give you an atmosphere of unparalleled nature and culture.

You will finish your hiking route once you arrive in Siena, a small town in population and very rich in tradition, heritage and history. We suggest you visit the Mangia Tower, with its altitude of 102 metres, and the Cathedral of Santa Maria Assunta.

During your trip you will have the opportunity to enjoy yourself by trying all the Tuscan gastronomy on each of the stages. Visit wine bars and trattorias and take back the photos you have taken of its landscapes and some of its exquisite wines and olive oils.

At the end of this tour you will be able to complete another of our hiking routes in Italy, for example, the one that takes you through another area in Tuscany from Montefalcione hasta Buonconvento; or even the last section of the popular Via Francigena, which will take you to Rome.

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 Florence

    Today you will arrive in the charming city of Florence, where we recommend you take a first walk to delve into the culture of Tuscany. Visit the Cathedral of Santa Maria dei Fiori and remember to stop by the famous Ponte Vecchio and take the respective souvenir photographs there.

    If you have a little more time, head to the Degli Uffizi Gallery, a palace and museum with one of the oldest art collections in the world. It is the ideal visit to know details about the essence and culture of the city.

    Overnight: Park Palace Hotel - Florence


    From Settignano to Fiesole

    To start your route today, you must take a bus on your own that takes you to the beginning of your route: Settignano. Once there, you will begin your journey crossing the 

    traditional Tuscan landscapes full of olive groves and Renaissance villages, while enjoying a stop or two to try the exquisite gastronomy that characterizes the Florentine area.

    Length: 8 km.

    Overnight: Park Palace Hotel - Florence


    Circular route in Greve in Chianti

    Today you will have an included transfer that takes you from Florence to the village where you will discover the essence of the famous Chianti wine: Greve in Chianti. Once there, you will have to leave your belongings at the hotel and then head to Le Cantine di Greve for an exquisite wine tasting.

    Once finished, you will have before you a circular route passing through Montefioralle, which will take you back to Greve in Chianti.

    Length: 9 km.

    Overnight: Albergo del Chianti - Greve in Chianti


    Circular route in Panzano

    Today you will find a landscape of typical Tuscan hills that surround the town of Panzano. You will discover coming across your path forests and vineyards that will take you to small farms in the middle of the road that you will love to know.

    As a curious fact, we tell you that in the 10th century, several aristocratic families from the Chianti area built fortresses and castles in Panzano, in order to protect their lands from possible invasions.

    Length: 11 km.

    Overnight: Albergo del Chianti - Greve in Chianti


    From Badiaccia Montemuro to Radda in Chianti

    Today you will have a transfer included to Monte San Michele, the highest point in the Chianti area. From there, you will descend through a chestnut forest until you reach Volpaia, a small medieval hamlet.

    We suggest you stop at a wine bar in the area to sample the traditional wines and then continue to your destination for today: Radda in Chianti.

    Once you arrive, we suggest you take a walk through Piazza Ferrucci, where you can enjoy photographing everything that stands in your way. The beauty of this village, located on a Tuscan hill, will delight you.

    Length: 12 km.

    Overnight: Palazzo San Niccolò Hotel - Radda in Chianti


    Circular route in Radda in Chianti

    For today we encourage you to discover the architecture and history in the centre of Radda in Chianti, as well as to visit its famous Castello di Brolio or the Church of Santa Maria Novella.

    Remember that your hiking trip in Tuscany is coming to an end, so if you haven't already, it's time to discover some of the typical wines from the area.

    Length: 16 km.

    Overnight: Palazzo San Niccolò Hotel - Radda in Chiant


    Free day in Siena

    Today you will have breakfast and then you will have a transfer included towards Siena, where you will have all day for yourself. Take care to discover each of the points of interest in this city full of history and culture.

    As a curious fact, we tell you that in Piazza del Campo de Siena is made the Palio de Siena, a horse race of medieval origin that takes place twice a year, once in July and once in August.

    Overnight: Chiusarelli Hotel - Siena


    Return from Siena

    Once you have breakfast, you will have the day off in Siena to enjoy its culture, its gastronomy and all the monuments that characterize it.

    From there, you'll need to take a bus or train to the city from where you have your flight back to your home city.* The nearest ones are Pisa and Florence.

    *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 hiking trail from Florence to Siena.

    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 Florence - Park Palace Hotel

    Accomodation in Florence

    Accomodation in Greve in Chianti - Albergo Chianti

    Accomodation in Greve in Chianti

    Accomodation in Radda in Chianti - Palazzo San Niccolò Hotel

    Accomodation in Radda

    Accomodation in Siena - Chiusarelli Hotel

    Accomodation in Siena

    Included services

    Accommodation in hotels.

    Rooms with private bathroom.


    Complete itinerary of your trekking route from Florence to Siena.

    Baggage transfer according to the itinerary.

    Transfers on days 3, 5 and 7.

    24 hours Telephone assistance on route.


    Additional services

    Additional single room: to consult.

    Extra nights (breakfast included): to consult.

    Dinners: to consult.

    Transfers to and from the airport.

    Guided tour in Florence.

    Guided tour in Siena.

    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 April and October. Spring and the beginning of autumn are the best times to explore the hiking trail from Florence to Siena.

    How do I get to the starting point?

    The best way to get to Florence is by plane, although it is a city with very good communications both by train and by road.

    The nearest airport is Florence Airport, from where you can reach the city centre by bus or taxi. It takes 15 to 30 minutes depending on the option chosen. 

    Pisa Airport is also suggested, from where the journey to the centre of Florence is approximately 1 hour.

    When you finish your route in Siena, you can return to Pisa or Florence by train.

    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.

    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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