Photo ©Shutterstock / Shchipkova Elena
Hiking and the Treno Natura through the Siena territory
Three days of slow tourism
125 KM
17 KM
3 days

A slow journey, marked by the jolts of rusted wheels and the rhythmic, measured stride that becomes a soundtrack to this trip back in time. The scenery is one of the most beautiful in Tuscany: Siena and the territory that surrounds it. Beginning in the Palio city, the train directs itself immediately into the enchanted landscape, passing alongside the Crete Senesi and through small villages frozen in time, Asciano, Trequanda, San Giovanni d’Asso, Torrenieri… Not to mention offering a glimpse of the profile of Monte Amiata. Returning toward the city, the train tracks brush by the elegant walls of Buonconvento and, hidden amongst the hills, the Abbey of Monte Oliveto Maggiore.

These are the most evocative stops of the Treno Natura, a period train that traces the old Asciano – Monte Antico line (now closed to regular traffic). Pulled by a steam locomotive or by a post-war diesel railcar, the train leads guests on a discovery of enchanted places, stopping in small stations where a vintage atmosphere still exists. Crossing through the Crete Senesi and the Val d’Orcia, the train runs all the way to the base of Monte Amiata, offering postcard-perfect views. Forgetting the trouble of car traffic, the Treno Natura isn’t just a method of transportation, but the protagonist in and of itself of a journey out of the ordinary, far from frantic rhythms, marked by pistons, blackened by soot and warm like the wooden benches that slowly traverse the landscape. Guests can get off the train at the old stations to participate in a series of itineraries that are perfect for excursions on foot or by bike, experiencing the territory close-up and tasting its culinary treats. Returning to the train, continue your journey toward historic beauty, faded over time but richer than ever before in vitality and the feeling of magic.

first day
A walk along the roads of art
 - Credit: Enrico Bottino

Siena is a mysterious and legendary city, full of secrets and curiosities – like the famous Palio – which make it a place unlike any of the other cities in the former Grand Duchy. From the Middle Ages to today, there have been an infinite number of historical events that have played out in the city, in its small rioni, its historic palaces, its artisan workshops and the terraces that overlook the lively landscape below.

The historical centre, almost completely located inside a Limited Traffic Zone, and its continuous ups and downs – thanks to being built on series of hills – make the city ideal for urban hiking: a different way to stumble across hidden beauties, an itinerary that opens you up to new discoveries and to getting lost in the most evocative little streets. We depart from piazza del Duomo, where the city’s splendid cathedral sits, home to works by Bernini and Nicola Pisano: you can’t miss the chance to visit the sacred building and the nearby Opera del Duomo Museum, from where you can climb to the top of the “Facciatone” and admire the city from above.

From the cathedral, continue through piazzetta della Selva and via del Fosso di Sant’Ansano, a place known for its legends, including the one about The Saint, the patron saint of the city, who was able to miraculously escape a martyrdom. Continue on via Ettore Bastianini, from where you can glimpse in all their beauty the medieval defense walls that connected Porta Laterina to Porta San Marco, and beyond these, the cypress trees that characterize the wavy, rural landscape around the city. Next, head down via della Diana, the street dedicated to the mysterious underground river that seemed to run under the medieval city, before arriving at Porta San Marco and its gardens, another place with panoramic views of the city. Moving toward the Fonte delle Monache, you’ll cross a stretch of via delle Sperandie, offering a stunning view of the countryside, and come to the historic fountain, a small and evocative cave preceded by an opening in the hillside that was once used by Sienese monks as a wash house.

After the fountain, turn toward Prato di Sant’Agostino and its church, another treasure chest full of frescoes and high-value works of art, then make a quick jump over to the Orti dei Tolomei, a designated park from where you can see the Valle di Valdimontone. On the left, a white and orange tower rises toward the sky. This is the Torre del Mangia, one of the highest in Italy, a symbol of the territory and an expression of the city’s power. In Siena’s elegant skyline, it’s said that the town hall’s tower was built to be the same height as the cathedral’s bell tower so as to support neither winners nor losers in the power of the Municipality and the church. And it’s at Torre del Mangia that our walk through the city ends, which you can get to via the Arch of San Giuseppe and the descent down via Dupré.

You’ll finally arrive in Piazza del Campo, a place that needs no introduction, the true heart of the city and home every year to the Palio. To best enjoy this splendid medieval scenery, you’ll want to climb the nearly 400 steps to the top of Torre del Mangia, where you can admire from above the spectacle around you, in the reds of the towers and houses and in the greens and yellows of the hills that paint the countryside beyond.

second day
Train rails through the Crete

A soothing atmosphere imbued with fresh air opens the second day of our trip. At the Siena train station, the modern regional trains arrive and depart alongside an old locomotive puffing steam, ready to adventure into the Crete Senesi, which are considered a UNESCO World Heritage Site for the value of their culture and landscape. The name of the train, Treno Natura, offers a clue to the scenery that will slide by us throughout this journey amongst small villages and fairy-tale landscapes. Each historic train leaves Siena in the morning and returns in the late afternoon, running along the Asciano – Monte Antico line for the whole trip, and stopping, according to the journey, in one or more stations along the line. At the stops, round-trip buses are guaranteed for those who would like to go to the most beautiful villages in the area, which are selected by the organizers based on their festivities, events and town sagre. For information: 

Final goodbyes, two mighty blows of the whistle and we’re off, the train leaves the city behind and is immediately immersed in the Tuscan hills: small farmhouses in the middle of nowhere, surrounded in the summer by fields of wheat and sunflowers, and a bare, lunar landscape in the winter, when the vegetation loses its leaves. The first stop: Asciano, a historic village, a crossroads of allusive roads, like the Lauretana leading to Siena and the spectacular white road of Monte Sante Marie. Asciano is home to the Basilica di Sant’Agata, with its museum of sacred art, as well as the Gothic and Late-Gothic churches of San Bernardino and Sant’Agostino.

The train continues through corners of the territory that can only be seen by train, before arriving in San Giovanni d’Asso, a sheltered, hillside village protected by defense walls. With a majestic puff, the train heads on to Torrenieri, a hamlet in the municipality of Montalcino and home of the Brunello DOCG wine from which it takes its name, before moving toward the valley of the river Orcia. The line continues along landscapes that occasionally become lunar-like as you approach Monte Amiata.

The train follows the river’s course as it goes west: the high plains slowly transform into a softer landscape and in just a few kilometres you’re at the Sant’Angelo – Cinigiano station, from where you can reach the medieval village of Sant’Angelo in Colle, at the top of the hill. We’re almost at our destination now, as the train plods along for a few more metres, when suddenly, in the distance, the large station of Monte Antico appears, a testimony to the past, when the station was an important junction for the rail lines.

Let’s step off the train to stretch our legs and marvel at the houses in the town, dating to before the year 1000 and in a position that dominated over the Ombrone Valley. The current residential centre developed in the late-1800s in the shadow of the medieval castle, which can still be seen today, thanks to the inauguration of the train line. Back on the train, we can once again admire the beauty of this territory through the window, before arriving in Siena at the end of this journey back in time.

third day
Buonconvento and the Abbey of Monte Oliveto Maggiore
 - Credit: Shutterstock / Lapas77

The third day has begun and we’re back on the train, this time in the direction of the Val d’Arbia, passing by the villages of Monteroni and Lucignano d’Arbia before reaching the end of our route: Buonconvento. This medieval village sits in the heart of the Crete Senesi, enclosed behind defense walls dating to the 1300s, when the municipality belonged to the governors of Siena. Its historic centre is made up of palaces and houses in red brick and is home to the Sienese Sharecropping Museum, officially known as the Museo della Mezzadria Senese, and the Museum of Sacred Art in the Val d’Arbia, located in the elegant Palazzo Ricci. After exploring the oldest part of the town along via Soccini and admiring the Palazzo Podestarile, with its civic tower and coats of arms of the podestà, come back to present day with a hike through nature, reaching the Abbey of Monte Oliveto Maggiore, one of the most evocative and hidden places in the Siena territory.

Taking the road toward Monte Oliveto, follow the Sentiero delle Crete n. 515: from the white road, the landscape is majestic and the views go on as far as the eyes can see between the hills of the Val d’Arbia, Montalcino and toward Monte Amiata. Continue your walk amidst olive trees and small farms until you arrive at Chiusure, a hamlet of Asciano that appears as if painted with warm, brick-coloured tones. From here, the Abbey is only a kilometre away. Commissioned by the Senese aristocrat Giovanni Tolomei so he could retreat into monastic life, it is home to a large church and an elegant cloister. The complex, decorated with fresco cycles and statues, is enriched by a large library where the Benedictine monks follow the practice of “pray and work,” leading a life of prayer and studies. Participating in an Olivetan mass with Gregorian chants is a truly mystical experience, even for non-believers.

Once at the Abbey, more experienced hikers can return to Buonconvento by going back the way they came, completing the tough day of hiking. It’s also possible to call a taxi to get back to Buonconvento or Asciano, and from there, you can catch a train to Siena.