Walking from Siena to Florence

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Walking from Siena to Florence

Distance: 82 km.

Duration: 10 days / 9 nights

Meals: Breakfasts and 2 dinners

Accomodation: Hotels and cottages

Price: From 1.176€ per person

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

Are you in love with Italian traditions? Do you like rural tourism to explore new places? On this walking trail from Siena to Florence you can visit the best of Tuscany and Umbria.

You will cross vineyards and olive groves, hills and plains where you will fall in love with its beauty and, at the same time, the diverse landscape that these two Italian regions have. You will walk through beautiful Renaissance cities such as Pienza, Montepulciano and Monticchiello. 

Your route will start in Siena, whose historic centre was declared a World Heritage Site by UNESCO in 1995. From there, you’ll continue your route through hills and long cypress trails passing, among many other cities, through Perugia, noted for having the oldest and most prestigious universities in Italy.

Finally, in Florence, your final destination on this route, take the time to visit the impressive Pitti Palace and the Uffizi Gallery. These will give you the ideal share of cultural to complete your trip.

As an interesting fact, we would tell you that Siena and Florence rivalled each other for many years as urban centres. Today, in both cities, you will discover architectural wonders that you will love.

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.

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 Siena

    Today you will arrive at your first stop on this walking route: Siena. In this historic city, declared a World Heritage Site by UNESCO in 1995, we suggest you start enjoying and getting to know its charming streets, as well as touring the Plaza del Campo with its singular fan shape.

    Overnight: Chiusarelli Hotel - Siena


    Free day in Siena and Montepulciano

    During the morning, you will have all the time you need to delight in the architectural beauty and gastronomic delights of Siena, visit its 12th century Gothic cathedral and take a walk around its churches and palaces.

    Once you finish your sightseeing tour, you will have to take a train that will take you to Montepulciano, where you will rest on your second night to start your first walk tomorrow.

    When you arrive at Montepulciano train station, you will have an included transfer that will take you to the hotel.

    Overnight: L'Agnolo B&B - Montepulciano


    Two circular route options

    For today we offer two different hiking options. In the first, you will have a transfer that takes you to Montefollonico, where you can take a spectacular walk around its extensive vineyards.

    In the second, your transfer will be in the direction of Pienza, whose historical and artistic heritage is concentrated mainly in the square that pays homage to Pope Pius II.

    From there, you will have to start your route by walking back to Montepulciano, located between two valleys, Val di Chiana and Val d'Orcia. Along the way, you will pass the spectacular fortifications of Monticchiello and, later, Poggio Tullio.

    As an interesting fact, we tell you that in Montepulciano some scenes of 'New Moon' were filmed, part of the famous “Twilight” saga.

    Option 1

    • Length: 14 km.
    • Duration: 3,5 hours

    Option 2

    • Length: 15 km.
    • Duration: 4,5 hours

    Overnight: L'Agnolo B&B - Montepulciano


    Walk to Acquaviva

    Today you will start your route very early in the morning, because at noon you will have an included transfer that will take you from the final stop on your route to your accommodation.

    You will walk from Montepulciano to the Acquaviva hills, passing through the classic Tuscan countryside and all the villages that decorate the hill until you reach the top.

    Once you are in Acquaviva, they will take you to Cortona so that you have all the afternoon free and enjoy its medieval architecture, walk along its hilly streets because of the hill where the city is located, and get to know first-hand the locations of the film 'Under the Tuscan Sun', engraved in this village of Etruscan origin.

    Length: 10 km.

    Duration: 2,5 hours

    Overnight: San Michele Hotel - Cortona


    Walk from Ossaia to Tuoro sul Trasimeno

    After your breakfast you will have an included transfer that will take you in a short time to Ossaia, where you will have to start your tour. You will enjoy the idyllic Lake Trasimeno that you will see in the distance and delight in the best of the views towards the Valdichiana Valley as you go on.

    You will arrive in the Umbria region, more exactly in Tuoro sul Trasimeno, from where you will have a transfer that will take you to Castel Rigone to spend your fifth night of this walking trip getting to know the best of the Tuscan and Umbrian regions.

    Length: 16 km.

    Duration: 5 hours

    Overnight: Villa Mina B&B Hotel - Castel Rigone


    Walk from Castello di Mongiovino to Panicale

    To start your day, you will be picked up at the hotel in Castel de Rigone to take you to the Castello di Mongiovino, where we suggest you visit the Renaissance-style Mongiovino Abbey.

    From there, start your walk to Panicale, whose main tourist attraction is the Church of San Sebastian. When you arrive, enjoy walking through its squares and enjoy good wine and a typical local lunch.

    Around 2 p.m. your transfer included for today will take you in half an hour to La Corte del Poggio, in the Perugia region. Tonight you'll have your evening meal included.

    Length: 12 km.

    Duration: 3 hours

    Overnight: La Corte del Poggio (close to Perugia)


    Wine-tasting in Monte Vibiano and walk to La Corte del Poggio

    The first thing you will do today will be to take a short transfer to Monte Vibiano to tour its vineyards there and enjoy an inclusive wine-tasting.

    When you're finished, you'll start the journey back to La Corte del Poggio along a flat path along the promenade that on some stretches borders the River Nestore.

    Tonight you'll have your evening meal included.

    Length: 13 km.

    Duration: 4 hours

    Overnight: La Corte del Poggio


    Walk from Monte Tezio to Perugia

    At the beginning of your day, you will have an included transfer to Monte Tezio that will last a little less than an hour. From there, you’ll start walking south towards Perugia. You will do so along a path of great historical relevance because it has been a source of drinking water for the city.

    When you arrive in Perugia, the capital of the Umbria region, your first impression will be to cross its immense arched door that gives way to its squares, markets and museums that will make you fall in love even more with the culture of the region. Visit Palazzo dei Priori, get to know the famous Fontana Maggiore and, if you have time, the Umbria National Gallery, located in a spectacular medieval palace.

    Length: 17 km.

    Duration: 5 hours

    Overnight: Fortuna Hotel - Perugia


    Free day in Florence

    Today you will take a train to Florence, where you will have all day to know at your own pace this city of contrasts. You can visit Piazza del Duomo, the Cathedral of Santa Maria del Fiore and its well-known Piazza della Repubblica.

    In addition, if you like art and its history, you must pre-book a ticket to the Uffizi Gallery, where you will fall in love with one of the oldest and most famous art collections in the world.

    Finally, after walking along its streets and through the city, we suggest you take as the traditional souvenir photo of Ponte Vecchio. However, do not take it on the bridge itself, but from one of the terraces that are located parallel to it from where you can also enjoy the views over the River Arno.

    Overnight: La Fortezza Hotel - Florence


    Return from Florence

    After breakfast, finish your rural hiking trip with us.* If you wish and have time before you leave, we suggest that you take an excursion to Pisa. It will take less than an hour to get there, you can visit it in half a day and you will leave with the memory of another of the most charming cities in Italy.

    *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 walking route from Siena to Florence.

    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 Chiusarelli Hotel - Siena

    Accomodation in Chiusarelli Hotel - Siena

    Accomodation in L'Agnolo B&B - Montepulciano

    Accomodation in Montepulciano

    Accomodation in San Michele Hotel - Cortona

    Accomodation in San Michele Hotel – Cortona

    Accomodation in Villa Mina B&B - Castel Rigone

    Accomodation in Villa Mina B&B Castel Rigone

    Accomodation in La Corte del Poggio 

    Accomodation in La Corte del Poggio

    Accomodation in Fortuna Hotel - Perugia

    Accomodation in Fortuna Hotel – Perugia

    Accomodation in Fortezza Hotel - Florence

    Accomodation in La Fortezza Hotel – Florencia

    Included services

    Accommodation in hotels and cottages.

    Rooms with private bathroom in hotels.

    Meal plan of your choice.

    Complete itinerary of your trekking route from Siena to Florence.

    Wine-tasting on the 7th day in Monte Vibiano.

    Transfers according to your itinerary from day 2 to day 8.

    Baggage transfer on days 4, 5, 6 and 8.

    24 hours Telephone assistance on route.


    Additional services

    Additional single room: to consult.

    Extra nights (breakfast included): 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 April and October. In this area of Italy, the best time is spring, so if you want to enjoy the most charming landscapes at their best, we recommend that you explore this walking route between April and June. Also the colour palette in autumn will make you fall in love, so September and October too are a great option. 

    If you decide to do it between July and August, you will have the warmest weather and beautiful sunny days, so we suggest you bring plenty of water and start each day very early to avoid the midday sun.

    How do I get to the starting point?

    To get to Siena, your starting point, the best option is to get to Florence Airport from where you can go to Siena by train (1 hour and 30 minutes) or by private transfer organized by Santiago Ways.

    At the end of your route, from Florence, you can take a taxi or bus on your own that will take you to Florence airport in about 30 minutes, or ask us to book a taxi in advance for you.

    If you fly home from Pisa, you can take a bus from Florence (1 hour and 15 minutes) to Pisa Airport or on a private transfer that you can also book.

    Remember, we can arrange a private transfer both at the beginning and end of your route. Ask us about this option at the time of booking.

    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.

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

    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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