Tuscany Walking Holiday

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Tuscany Walking Holiday

Distance: 62 km

Duration: 6 days / 5 nights

Meals: Breakfasts

Accomodation: Hotels and farmhouses

Price: From 791€ per person

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

If you love discovering medieval cities while enjoying landscapes of green hills and extensive olive groves, the Tuscany hiking trail is the trip you’re looking for. You will discover extensive wine-growing areas and fascinating monasteries. Encourage yourself to live the experience!

You will start your trip in Montefalcione, a small town with easy access to which you can reach from Rome, Pisa or Florence. You will get to know all the charm of southern Tuscany, such as its thermal baths in Bagno Vignoni or its UNESCO heritage cities, such as Pienza. You will reach the end of your route in Buonconvento.

Remember that if you are passionate about walking, once you finish your trip in Tuscany, you can join another of our proposals for hiking routes in Italy: Hiking in Cinque Terre, or on the Amalfi Coast on the Vía Francigena.

Throughout Tuscany you will find unparalleled food and wines, so remember to take all your walks calmly so that you can enjoy some of these delicacies: Pecorino cheese, wines with denomination of origin or truffles.

You will visit the Abbey of Sant’Antimo, one of the most important architectural jewels of the Tuscan Romanesque; Also, the famous area of ‘Crete Senesi’, an immense series of hills and forests south of Siena.

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 Montepulciano

    Today you will arrive in Montepulciano, for which we suggest you access from Rome, Pisa or Florence. You can do it first by train and then arrive by taxi, while you start to enjoy the beauty of the Tuscany landscapes.

    As a curious fact, we would tell you that this village, located on a hill with impressive panoramic views, with a typically medieval appearance, is known for its extraordinary red wines, with the Nobile Wine of Montepulciano as the best known.

    Overnight: Montepulciano


    From Montepulciano to Pienza

    For your first day of walking, you should start walking from the Church of San Biagio until you reach Monticchiello, where we suggest you stop for a good coffee and taste the typical food of the region.

    Once you arrive in Pienza, you will find yourself in one of the most elegant cities in Tuscany and where you will have the opportunity to try the authentic and famous Pecorino cheese. During the afternoon, walk along the Corso Rossellino, the main road.

    Length: 15 km

    Overnight: Pienza


    From Pienza to the Bagno Vignoni Springs

    On this day you will walk surrounded by hills, forests and picturesque villages that will take you to the thermal springs of Bagno Vignoni, where we advise you to enjoy a good hot water bath that arises naturally from the subsoil.

    The town of Bagno Vignoni was always a thermal centre where all social classes could attend to enjoy its hot springs and take advantage of its benefits. In addition to the baths, we recommend visiting the old natural pool in the village and getting close to the famous Osteria (hostel) behind the pool.

    Length: 16 km

    Overnight: Bagno Vignoni


    From Bagno Vignoni to Montalcino passing through Sant'Antimo

    During your fourth day on the road, a quite difficult hike through the dry riverbeds of the area awaits you until you reach the beautiful Abbey of Sant'Antimo, a monastic complex founded in 750, which bears the title of a major architectural jewel of the Tuscan Romanesque period.

    After you visit the Abbey and discover its history and legends, you will have an included transfer that will take you to Montalcino, where you will stay tonight.

    Length: 14 km

    Overnight: Montalcino


    From Montalcino to Buonconvento across Crete Senesi

    For this day, we advise you to leave with a lot of energy, because you will have a long but charming journey, before you reach the final destination of your hiking trip in Tuscany. You will pass through the Brunello region, where the vineyards and olive groves will be in your wake.

    Then you will advance through the hills and forests of Crete Senesi and enjoy its particular geological formations, as well as the urban oasis that you will encounter as you walk. When you finish the day, in Buonconvento, we advise you to take a walk through its ancient walls and the Podestá Palace.

    Length: 17 km

    Overnight: Buonconvento


    Return from Buonconvento

    Today you have a transfer included from your hotel in Buonconvento to Buonconvento train station. From there, you can head back to Rome, Pisa or Florence, wherever it will be most comfortable for you to take your flight back to your home city.*

    If you are passionate about walking, once you finish your trip in Tuscany, you can join another of our proposals for hiking trails in Italy: Hiking in the Cinque Terre, Hiking along the Amalfi Coast or the Via Francigena.

    *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 of the hiking routes through Tuscany.

    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 B&B L'Agnolo - Montepulciano

    Accomodation in Montepulciano

    Accomodation in San Gregorio Residence - Pienza

    Accomodation in Pienza

    Accomodation in Le Terme Hotel - Bagno Vignoni

    Accomodation in Bagno Vignoni

    Accomodation in Dei Capitani Hotel - Montalcino

    Accomodation in Montalcino

    Accomodation in Fattoria Pieve a Salti - Buonconvento

    Accomodation in Buonconvento

    Included services

    Accommodation in hotels and farmhouses.

    Rooms with private bathroom.


    Complete itinerary of your trekking route in the Tuscany.

    Baggage transfer.

    Transfers during days 4 and 6.

    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.

    This route can be done between the months of March and October. Please note that July and August can be very warm months to complete the route.

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