The route is quite easy, with ups and downs typical of the Tuscany’s rolling hills. The whole itinerary is mostly on paths and gravel roads (strade bianche), even if you will find some sections on asphalted road. Some walks can be shortened if requested in advance.
Start: Montepulciano Finish: Siena
Your Tuscan walking begin in the medieval and Renaissance hill town of Montepulciano. Montepulciano is easily accessible via Rome, Florence or Pisa; catch the train to Chiusi then take a local bus or a short taxi ride to Montepulciano. Admire the impressive views over the rolling Tuscan landscape that you’ll be exploring over the next week.
Set off from San Biagio church on a quiet rural track and suddenly you’re lost in peaceful beauty. Soon you come upon the peaceful village of Montichiello, where you can pause for a relaxed lunch or perhaps just a quick cappuccino on the way to Pienza.
Picture-perfect Pienza is a UNESCO World Heritage Site brimming with unique Renaissance architecture. AND it is home to delicious pecorino cheese and tasty truffles. The ideal spot to indulge in Tuscan treats!
Challenge: 4 hours, 13/15 km, 385 m ascent, 505 m descent
Wander through impossibly perfect landscapes of rolling hills, majestic oaks, cypress trees and photogenic villages. Stop to rejuvenate at the hot springs in Bagno Vignoni and trade the warm Tuscan sun for steaming medicinal waters.
Challenge: 4 hours, 12 km, 195 m ascent, 420 m descent
Test your legs on a more challenging -but very rewarding- route as you follow dramatic arid ravines through wild surroundings to the remote Sant’Antimo Abbey, perfectly situated in a pastoral landscape. Take time to explore this mysterious 750 A.D. monastic site then jump in the taxi for the transfer to Montalcino.
Challenge: 5 hours, 14 km, 225 m ascent, 185 m descent
A hearty breakfast will set you up for a long but enjoy day of walking in the famous Brunello wine region, passing vineyards and olive groves, then again entering the beautiful Tuscan landscape of the Crete Sensi and Buonconvento.
Challenge: 5 hours, 15/18 km, 316 m ascent, 619 m descent
A short day which is full of ups and downs, beginning with a transfer to the monastery at Monte Oliveto Maggiore, an impressive abbey built of red brick and set in the rugged Tuscan landscape. After an early visit to avoid the crowd, walk back to Buonconvento.
Challenge: 5 hours, 14 km, 382 m ascent, 460m descent
A short transfer takes you to Monteroni d’Arbia then you head toward Siena on foot, hiking hills and hamlets till the city's unmistakable silhouette begins to materialize in the distance. At Arbia you catch the train into Siena, then spend the evening wrapped in its magnificent beauty: the grand Piazza del Campo, delightful Duomo and medieval palaces recalling the city’s ‘contrade’ who ride in the risky ‘il Palio di Siena’.
Challenge: 4 hours, 10 km, 225 m ascent, 185 m descent
Your self-guided walking holiday comes to an end today after breakfast. Departure from Siena.
We use selected 3* and 4* hotels and agriturismo. Some of the accommodations chosen have a swimming pool and internal restaurant. They have been carefully selected for their location, atmosphere and/or unique services. All rooms are en-suite. Some of the hotels we work with appear here. If a certain hotel is unable to confirm due to lack of availability, we will request a similar one and inform you about the alternative booked.
Extra nights: Extra nights can be booked at any of the accommodations along the way.
The Duomo hotel, in Montepulciano’s old town centre near the Piazza Grande, is a small, welcoming family-run hotel situated in an old Renaissance Palazzo. What sets the Duomo apart is the attention we pay to our guests, creating a relaxing and intimate atmosphere for the duration of your stay.
Il Giglio is located in the Historic Center of Pienza, in Val d'Orcia, in a Renaissance Palace dating back to 1468. Completely renovated in 2000, already owned by the grandparents of the host Roberta who continues, every year, to renew and improve the location to welcome you in a unique environment.
This isn’t an ordinary bed & breakfast in Val d’Orcia, it isn’t just a ‘place to sleep’, it’s a refuge where charm and romanticism blend with simplicity. The Locanda del Loggiato dates back to 1300, it will take you back in time and allow you to discover the delights of one of the most magical spa villages in Tuscany, Bagno Vignoni.
This B&B is located in front of the ancient tower of the Palazzo Comunale. The windows overlook the Piazza del Popolo that has always marked the life of the Montalcinese and the many visitors who cross it, looking up you get lost in the beautiful hills of the Val d'Orcia, among the woods, vineyards, large olive groves, up to Pienza and San Quirico d'Orcia.
The Borgo of Pieve a Salti is nestled in the rolling hills of Siena, in a beautiful natural setting, rich in history, art and sacred traditions. Its houses, inside the old village overlooking the surrounding hills, offer you hospitality in comfortable rooms with bathroom or typical apartments of various sizes .
Hotel Chiusarelli is located right in the historical centre of Siena, city of art that still nowadays remains rooted in its traditions, among which is the famous Palio. The hotel is set in a neoclassical villa built in 1870. The renovation has added a modern touch keeping, however, the original style of the palace that, with its magnificent frescoed rooms, makes our guests feel like stepping back in time.
Departure an day of the week, subject to availability, from April 1st until october 31st
Arrival at Montepulciano
From the airports you can take a train and then busses to reach Montepulciano.
BY TRAIN FROM THE AIRPORTS TO MONTPULCIANO
From the two major Rome airports take the bus or train to Rome Termini train station. From Roma Termini train station take the direct train to Chiusi-Chianciano Terme (train ride takes approx. 1 hour and 40 minutes, ticket costs 9,95 Euros) From Chiusi-Chianciano Terme take the bus to Montepulciano (line FT4 bus ride takes 25 minutes) www.sienamobilita.it
From Florence airport take the bus Florence Santa Maria Novella train station. From Florence train station take the direct train to Chiusi-Chianciano Terme (train ride takes approx. 2 hours and 15 minutes, ticket costs 13,50 Euros) From Chiusi-Chianciano Terme take the bus to Montepulciano (line FT4 bus ride takes 25 minutes) www.sienamobilita.it
Departure from Siena
BY TRAIN FROM SIENA TO THE AIRPORTS
Check the updated timetables on the website www.trenitalia.com
To Pisa Airport: From Siena take the train to Pisa Centrale. Train journey to Pisa takes approx. 1 hour and 45 minutes, ticket costs 10,70 Euros. From Pisa Centrale you can take a bus, train or taxi to reach Pisa Airport.
To Florence Airport: From Siena take the train to Florence Santa Maria Novella Train journey to Florence takes approx. 1 hour and 30 minutes, ticket costs 9,10 Euros. From Florence Santa Maria Novella you can take a bus or taxi to reach Florence Airport
GPS tracks are available on request