Tour of the Sienese

Through the gentle hills of Siena

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Walking routes, horse trekking, urban trekking or itineraries for bikers, Trenonatura… thousands are the opportunities to get to know, discover and experience the immense natural heritage of the Terre di Siena. Hundreds of kilometres of paths and white roads follow their wonderful and ever-changing landscape, from the summit of the Amiata to the plains of Val di Chiana, from Chianti to Val’ Orcia, to the Val di Merse and Alta Val d’ Elsa. A simple walk is enough to feel the consistency of the Terre di Siena, and to understand that travelling slowly means living fully, in the sign of true wellbeing, the harmony of a timeless landscape in continuous movement. In 1996, the Provincial Administration of Siena ( established 14 nature reserves that together occupy an area of eight thousand hectares, in order to preserve the immense value of the flora and fauna of this territory. Parks and reserves are open to visitors who wish to meet animals in their natural habitat.

The Lands of Siena contain a historical, artistic and environmental heritage of great interest that few other places in the world can boast. The landscape is in eternal motion: just stop a few moments to observe the undulating horizon, the cypresses rustling in the wind, the shadows that move from sunrise to sunset, the trajectories of paths seemingly without end, the flocks that draw curious white geometries….. in short, walking in these parts means to fully live the harmony of a timeless place, enjoying the balance of tranquility and the emotion of discovering the silence of ancient and fascinating places. The curiosity of discovering the alleys, squares, courtyards and palaces of Siena inspires the adventure of urban trekking, while the Etruscan mysteries crowd the mind of those who set off towards Murlo, the scent of must and wine draws trajectories between the vineyards, the wine cellars and castles of Chianti, while the water is the trail to follow in a path of thermal wellness that goes from Crete di Rapolano Terme, Val di Chiana, Val d’ Orcia, Monte Amiata. The 34 itineraries that the CAI has chosen are only a small selection of what the Terre di Siena can offer to those who travel on foot.

Via Francigena
For lovers of walks, the Via Francigena is the route par excellence to walk along on foot. The road, which in the past, especially in the second millennium, was travelled every year by thousands of pilgrims on their way to Rome “in search of the lost Heavenly Homeland”, is still today one of the most suggestive routes to travel without any means of transport other than their own legs. The road also crosses the province of Siena on its journey from Canterbury to Rome. Here below we report one of the most beautiful legs in Tuscany.

Leg: From San Gimignano to Monteriggioni
Distance: 29.8 km
Time: 7.30 ore
Climb: 513 m
Descent: 563 m
Max altitude: 320 m
Difficulty: Challenging

Departing from San Gimignano, head towards the Benedictine abbey of Monte Oliveto Minore. After passing the village of Santa Lucia, you go up a valley and reach the castle of Montauto. At this point our itinerary continues towards the Torraccia di Chiusi, tower-castle of the Abbracciabeni, and, after crossing the river Foci, towards Molino d’ Aiano, site of one of the stations mentioned by Sigerico (Sce Martin in Fosse). After reaching the Abbey of Coneo, an abbey of Longobard origin that belonged to the monks of Vallombrosiani, the road crosses the villages of Quartaia, Fabbrica, Onci, the mill of Calcinaia and the ford of Elsa at Gracciano, where the station of Aelsa was located. Just a little further ahead awaiting you are the Bagni delle Caldane, from the Etruscan-Roman period, the fortified village of Strove, built in 994 by the lords of Staggia, the castle of Petraia and the Badia a Isola, an important monastery built in the X century, which Sigerico calls Burgenove station. Our journey ends at the castle of Monteriggioni, a town fortified by the Sienese in 1213.


Cyclists are welcome in the Lands of Siena. In this that is the land of all cyclists, from children who travel on the seat, to cyclists who cycle to discover the world, from adventurous bikers in search of winding roads to cyclists who love elegant road bikes, in addition to magnificent roads you can find a welcome that takes into account every need. The bicycle is a suitable device for recovering lost rhythms: between curves, descents, ascents, ridges and valleys, hills and roads that play with the force of gravity, wheels and pedals follow tracks that appear and disappear in the dimension of a landscape in eternal movement and changeable at every season, silvery as the winter sky, shining in spring, dazzling in summer when the grain is high. The Lands of Siena offer two permanent routes accessible to tourists, the Heroica and the Trail of Remediation. For a two-wheeled holiday, the cyclist can count on a specialized hospitality dedicated to him, and selected structures able to offer a series of useful services.

The Eroica
The roads of the Heroica wind for about 200 kilometers in the heart of the Tuscan Sienese, crossing unique and spectacular places such as Chianti, Crete and Val d’ Orcia. It’s a climb and descent of dirt roads that must be traveled with the right spirit, with the spirit of those who want to enjoy in peace every single moment and appearance of this magical land. The most trained will be able to organize a route in stages during which you can rest in the various lodgings that rise along the route, while those who are newcomers can integrate the bike route with the Treno Natura.

Distance: 205 Km
Time: 3/5 giorni
Difference in level: 3.500 m
Dirt Roads: 112 Km
Difficulty: challenging

The route, completely indicated with road signs, starts at Gaiole in Chianti. From here, riding on white roads, you enter the world of Crete made of large spaces and wavy horizons. After passing the first inhabited centre, Murlo, land of Etruscan people, and the Ombrone, one of the most challenging sections of this route awaits us, that of Castiglion del Bosco that leads to the spectacular hill of Montalcino near Passo del Lume Spento. At this point, making your way through the Brunello vineyards, you will reach the point where Val d’ Orcia meets Val d’ Asso. Near Torrenieri you take one of the most beautiful white roads in Tuscany, that of Cosona, along which you can reach the small village of Lucignano d’ Asso and San Giovanni d’ Asso, home of the truffle. At this point only 10 kilometres of the white road of Pieve a Salti separate us from Buonconvento.
Returning to the magical landscape of Crete, we will cross two of the most beautiful and exciting white roads of this journey: the Via di Montacuto and the extraordinary Via di Monte Sante Marie. After leaving behind Asciano and Castelnuovo Berardenga, we return to Chianti. Wheat fields and mills leave space for the vineyards again. At this point, the last final stretch awaits us, the road of Vagliagli, which leads us to Radda, Vertine and Gaiole, the departure and arrival of this splendid journey on two wheels.


An alternative means of transport to visit these magnificent lands is the bike. Here you will follow some itineraries that will lead you to discover some of the most beautiful roads in Tuscany and Italy in general.


Eremo di San Salvatore di Lecceto

ITINERARY 1: Via Cassia, the most classic crossing 

Departure: Siena
Arrival: Radicofani
Distance: 72 km
Time: 1 giorno

La Cassia is the historical road par excellence that connects Siena with Rome, an ancient consular road that witnessed the change of time through the centuries overlooking a Tuscany so typical that everyone dreams. It’s a fast road that invites you to relaxed driving, and awakens the pleasure of following with your eyes a landscape always in motion.

From Siena, head south, following signs for the S.S. 2 “Cassia “. The road leads almost immediately into the sunny Val d’ Arbia, crossing places of great historical importance, and for the most part follows the historic Via Francigena, permeated by the ancient spirituality of pilgrims who from Canterbury pointed towards Rome. The intermediate stages of the first section are the villages of Monteroni and Lucignano, which mark the route before reaching Buonconvento. We are crossing one of Italy’s historic granaries, where people and architecture speak of a rural landscape that is still basically intact. The most important traces of history and an ancient peasant civilization of this land are the grance, or rather large grain and food stores that, among other things, were also a support point for poor people, pilgrims and sick people in need. In the Middle Ages, the grance were rural buildings inserted in abbey complexes with a function of conservation of agricultural products, characterized by an imposing defensive structure. Along this route, just before the village of Monteroni d’ Arbia, you will find one of the most important grance, the one of Cuna.

The Cassia reaches after 27 km Buonconvento, historically a place of meetings, clashes and exchanges. In its rectangular plan, formerly bordered by a boundary wall, there are monumental buildings that bear witness to an important past: in addition to the Palazzo Comunale (with 25 coats of arms of the same number of Podestà who ruled the city until 1270), worthy of a visit is the Museum of Sacred Art of Val d’ Arbia in which, in a splendid Liberty context, are gathered works from churches and pievi scattered throughout the territory of Crete. After passing Buonconvento, the Cassia follows more sinuous trajectories and, shortly after Torrenieri, overlooks the unmistakable landscape of the Val d’ Orcia near San Quirico. It is here that perhaps most famous glimpse that identifies the Tuscan landscape opens up, characterized by the group of cypresses that emerge from the undulating lands. It is here that the most spectacular section of the Cassia begins, passing between Montalcino and Pienza, reaching the village of Bagno Vignone, with its magnificent water square, and it is here that a virtual journey begins which has water as its main theme. From the San Quirico Mulini Park and the thermal waters of Bagno Vignoni you can continue, at the foot of the Amiata, to Bagni San Filippo, another thermal village where water flows from the earth’s veins at about 50 degrees. From here you leave the Cassia track and turn left towards the spectacular fortress of Radicofani, from whose tower you can enjoy an unforgettable views of the Val d’ Orcia. The castle of Radicofani had a remarkable strategic importance on the Via Francigena, and links its fame to the history of Ghino di Tacco, a Sienese Ghibelline rebellious (quoted by Dante in the sixth song of the Purgatory and by Boccaccio in the Decameron) who, expelled from Siena, established here his residence, starting point of departure for his raids.
Important final detour to continue along the path of the thermal waters is that for San Casciano dei Bagni, a place just right to find comfort in the warmth of relaxing vapours at the foot of Mount Cetona, immersed in an environment rich in history and nature.

ITINERARY 2: Between Val d’Orcia and Val di Chiana
Departure: San Quirico d’Orcia
Arrival: Chiusi
Distance: 44 km
Time: 1 day

One of the most popular routes for lovers of two-wheelers is certainly the road that connects Val d’ Orcia to Val di Chiana, crossing the Sienese from west to east. A succession of wide green spaces, endless rows of cypress trees and ancient villages, which will make you enjoy the true sense of peace and freedom. This wonderful journey begins in San Quirico d’ Orcia, a characteristic village where the Collegiate Church of Saints Quirico and Giulitta, the Church of Mercy, Palazzo Pretorio, Palazzo Chigi, but above all the Horti Leonini, sixteenth-century Italian gardens designed by Diomede Leoni, where exhibitions of contemporary sculpture are organized. Leave the village behind you and continue towards Pienza. Known as the “ideal city”, Pienza has one of the most beautiful historical centres in Italy, so much so that it was declared a UNESCO World Heritage Site in 1996. Designed in the mid-fifteenth century by Bernardo Gambarelli known as the Rossellino, architect of the school of Leon Battista Alberti, the centre like the whole city in general is an expression of humanistic and Renaissance ideals. Another intermediate stop of your trip is Montepulciano, here you can take a tour through the cellars of the village, tasting the fine Tuscan wine, the Nobile di Montepulciano. From the wine we pass to the waters of Chianciano Terme, one of the most famous thermal resorts in Italy, where body care and relaxation are at home. This fascinating and exciting journey ends in Chiusi, a mysterious town that has its origins in Etruscan history. A world worth discovering is hidden in the underground, rich in catacombs and tunnels such as the “Labyrinth of Porsenna”.

One of the ways to fully enjoy the size of the Lands of Siena is to travel on horseback. In this way the journey, the movement, the paths, can abandon the obligatory routes travelled by men and engines and follow paths that wind through the heart of a landscape made of loneliness and inner recollection. Discovering the Lands of Siena on horseback means entrusting oneself to the senses to fully live the perception of a moving landscape, and to integrate perfectly in a pure environment far from tourism as a consumer good. Eight are the routes suggested by APT, real journeys immersed in the nature of one of the most beautiful landscapes of Tuscany. The description of the routes is indicative, so we recommend that you contact associations and guides in advance before embarking on the trip. If you have to rely on specific services to do equestrian tourism, the Terre di Siena offer facilities that provide logistical support to those who move along itinerant routes in stages, and to travellers who choose to make daily routes starting from a fixed base. Fundamental services are the possibility of accommodation for horses and riders, horse hire, courses for various disciplines and guided excursions, but also the retrieval of cars and trailers for the transport of horses.

ITINERARY 3: The Anello di Siena
Departure: Eremo di Lecceto, Comune di Siena
Arrival: Eremo di Lecceto, Comune di Siena
Distance: 60 km
Time: 9 hours in 2 legs

First Section: Eremo di Lecceto – Monaciano Farm
Distance: 25 km
Time: 4 hours
Our itinerary starts from the Eremo of Lecceto, a convent of Augustinian nuns dedicated to the cloister of which you can visit the kiosk and the church. From here, along a path from the 1100’s stone bottom, you reach Castello del Palazzaccio, dominated by the eighteenth-century villa. Beyond the modest centre and past the Fosso dell’ Arnano, a hydraulic work commissioned by Grand Duke Pietro Leopoldo I to facilitate the reclamation of the Pian del Lago, we arrive at Carpineto and Fogliano, the latter famous for its Roman parish church of 1300. From here the magnificent hilly area of Crete begins, one of the most fascinating and suggestive parts of the itinerary.

Bagno Vignoni


Second section: Monaciano Farm – Eremo di Lecceto
Distance: 35 km
Time: 5 hours
The second section is characterized by a completely new landscape, once you reach the historical farm of Monaciano, the clay leaves space for tuff opening onto the typical Chianti landscape characterized by hills, white roads, woods and vineyards. Once you cross Valiano, near which lies the stables of Luigi Bruschelli, known as “Trecciolino”, one of the best jockeys of the Palio di Siena, you go back to Vignaglia reaching the area of Pian del Lago where the Montagnola Senese begins. From here you reach the fourteenth-century hermitage of San Leonardo al Lago. Now the final stretch of our itinerary begins, which will take us back to the hermitage of Lecceto.

ITINERARY 4: From Montalcino to Chianciano Terme
Departure: Orcia – Asso Junction, Municipality of Montalcino
Arrival: La Foce, Municipality of Chianciano Terme
Distance: 28 km
Time: 5 hours

FIRST SECTION: Orcia e Asso Junction – Bagno Vignoni
Distance: 10,2 km
Time: 2 hours
The first part of our itinerary begins in the Artistic and Natural Park of Val d’ Orcia, where the Orcia and Asso rivers meet. Passing through woods and fields you will reach the farms of Santa Barbara and Caggiolo and the thirteenth-century castle of Ripa d’ Orcia, today used as a tourist company. Here the magnificent view of the valley will leave you breathless. At this point, head towards San Quirico d’ Orcia and then descend towards the course of the Orcia River opposite Podere Le Mulina. Our first stretch ends in the characteristic thermal village of Bagno Vignoni, famous for the large swimming pool of boiling water located in the main square and surrounded by buildings built by Bernardo Rossellino in honor of Pius II, and the loggia where Santa Caterina da Siena stopped. You will be fascinated by the view of the village at sunset, as Lorenzo il Magnifico himself was fascinated, who spent a period here in 1490.

SECOND SECTION: Bagno Vignoni – La Foce  
Distance: 16,5 Km
Time: 3 hours
Returning to our journey from Bagno Vignoni, we continue towards Via Cassia to reach the Corso dell’ Orcia. At this point, following the paths that line the watercourse you will find yourself wandering the Tresa creek, not far from the fortified village Castle of Spedaletto. Ride to the point where the Orcia River flows into the Formone, visiting the beautiful farms of Poggio Meriggi, Torricelle, Casalta and Casanova. Streets framed by cypresses will take you to the provincial road that connects Monte Amiata with Cianciano Terme. Once you reach the Fattoria della Foce, a beautiful Renaissance castle, the journey towards Chianciano Terme and the Val di Chiana is now almost at its end.

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