Via Lauretana by bike: route and unmissable stages

The Via Lauretana is the perfect route for both cycling enthusiasts and those who want to discover the traditions of Tuscany and admire the beauty of its landscape. In just a few stages, starting from the magnificent medieval city of Siena, passing through Valdichiana and touching briefly on Val d’Orcia, you can observe the marvels of areas such as the Crete Senesi, and the architectural and artistic works created over the centuries by the people who have inhabited this extraordinary region. Let’s find out everything you need to know about Via Lauretana and its unmissable stages. 

Stages of the Via Lauretana

The Tuscan Via Lauretana is one of the oldest routes in Italy. Initially built by the Etruscans to connect the city of Siena with the town of Cortona in the province of Arezzo, today it is one of the most popular and followed routes for cycling enthusiasts and those who want to admire breathtaking landscapes combined with magnificent historical sites of interest. You can tackle the 114.5 km trip in just five days, dividing it into six stages. The Tuscan Via Lauretana is a route for beginners and is also suitable for those who are not very fit and want to train for more demanding routes such as the Via Francigena or the Camino de Santiago de Compostela. Here, in detail, are all the unmissable stages of the Via Lauretana route.


The first stop on the Tuscan Via Lauretana is Siena, one of the most characteristic medieval villages in Italy and recognised by UNESCO as a World Heritage Site. In fact, even before you start the tour, the countless beauties of Siena will leave you awestruck: from the historical centre, with the spectacular Piazza del Campo and the Torre del Mangia, to the Gothic churches, Cathedral  complex and all the narrow streets and alleys where you can breathe in the authentic medieval atmosphere as if time had never gone by.  

Siena is therefore the starting point for this cycling route and, precisely for this reason, many people decide to organise an overnight stay the night before departure to fully enjoy the beauty of the city ahead of the five-day Via Lauretana. 

Crete Senesi and Asciano

Leaving Siena behind, the first section of the Via Lauretana route opens up in the evocative setting of the Crete Senesi, the magnificent natural landscapes that, over time, the rain and wind have moulded into clay hills. Continuing along the road, before arriving in the municipality of Asciano, you can admire medieval structures such as the castles of Leonina and Mucigliani or the historic hamlets of Vescona and Pievina.


On the way to Sinalunga, an unmissable stop is Rapolano Terme, a small municipality located in the heart of the Tuscan hills, where you can relax in the spas and visit the best vineyards in the Val di Chiana. After this short, relaxing stop, you will be ready to get back in the saddle and ride through almost 20 km of cultivated fields and forests, where you can admire ancient religious buildings such as the Church of the Madonna del Soccorso, dating back to the mid-1500s, or the Convent of San Bernardino. After this stage, you finally reach Sinalunga, a small medieval village rich in history and traditions: an absolutely unmissable stop. 

Torrita di Siena

Continuing the route along Via Lauretana, the fabulous Valdichiana Senese unfolds, a valley rich in history and traditions, where you can still touch the heritage left by ancient populations, such as the Etruscans and the Labyrinth of Porsenna, a maze of underground tunnels built by the Etruscan king Porsenna in the 6th century, which today lies beneath the village of Chiusi. Leaving Chiusi behind, you arrive at Torrita di Siena, a very characteristic medieval village, still surrounded by walls dating back to the 12th century. 


Toward the end of the route, you reach the magical medieval village of Montepulciano, a real gem located in the heart of the Tuscan hills, not far from Siena. Known above all for the production of the famous red wine Nobile di Montepulciano, this place also offers a priceless view of both Valdichiana and Val d’Orcia, thanks to its strategic position on top of a hill.


Leaving Montepulciano and travelling the last few kilometres of the Tuscan Via Lauretana, we arrive in Cortona, a welcoming medieval town in the province of Arezzo, near the border with Umbria. In fact, in Cortona, the Via Lauretana of Siena rejoins the original route of the Via Lauretana to Loreto. On this final stage, we can admire wonderful buildings dating back to both the Etruscan period and the medieval period, and be enchanted by the rich historical tradition that envelops the entire city. 

In conclusion, if you’re wanting to organise a different kind of bike tour, the Tuscan Via Lauretana is the route for you. In just a few stages, you can savour the beauty of Siena and its surroundings, and fully appreciate the characteristic natural landscapes and priceless historical heritage that distinguish these places. Finally, don’t overlook the option of riding the Via Lauretana in the reverse direction to that indicated above. In this case, the magnificent city of Siena is the finish line after five days of strenuous cycling and the ideal destination for the final days of your holiday, enjoying the local cuisine and wonders of the city. 

I Comuni di Terre di Siena