• Discover
  • Route planner
  • Features

Cycling between Siena and Cortona – la Via Lauretana in Tuscany

Giacomo Tuscany_Bike_Guide

Cycling between Siena and Cortona – la Via Lauretana in Tuscany

Bike Touring Collection by Francesco | Cyclo Ergo Sum



4-4 h

/ day

77.1 mi

6,675 ft

6,025 ft

The Via Lauretana is an ancient road whose history begins in Etruscan-Roman times. It was an important military and commercial route, thanks to which Siena was supplied with food and goods. Its name is more recent and is linked to the pilgrimage that many began to undertake from Siena to Loreto, to the Holy House, which, according to tradition, had been brought from Nazareth to the town in the Marches.

This Collection recounts the journey on the Via Lauretana as it passes through Tuscany, from Siena to Cortona. This section covers around 125 kilometres (80 mi) through the fantastic Crete Senesi through a sea of clay and hills of changing colours, characteristic ancient villages and unforgettable views.

Along the way, you’ll pass through villages such as Siena, Asciano, Rapolano Terme, Sinalunga, Torrita di Siena, Montepulciano and Cortona. It’s a breathtaking journey that’s suitable for all abilities.

You'll start in Siena, a UNESCO heritage site, which you can reach easily by train, passing through its unmissable historic centre with Piazza del Campo and the Duomo. You'll then cross the area between Asciano and Rapolano Terme, the well-known Crete Senesi, with its clay hills shaped by time and weather, yellow or green depending on the season.

Next, you’ll ride through the Sienese Val di Chiana, between the villages of Sinalunga, Torrita di Siena and the imposing Montepulciano, a valley that recalls the passage of the Etruscans and then the Renaissance. Finally, you'll reach Cortona, a cosy medieval town in the province of Arezzo, whose gates you can enter to admire its marvellous buildings dating back to both the Etruscan and medieval periods. Or, you can look out from the panoramic balcony of its Piazza Garibaldi to catch a glimpse of Lake Trasimeno and Mount Amiata on the horizon.

As well as the breathtaking nature and unforgettable views, don't forget to immerse yourself in the Tuscan food and wine culture: from the novello (new) olive oil to the tasty soups, home-made first courses to main courses such as Fiorentina or Cinta Senese cold cuts, all washed down with good Montepulciano wine or craft beer from Trequanda.

The start and finish points are well-connected by public transport, so you'll have a convenient train to reach Siena on departure and return from Camucia, just below Cortona.

What are you waiting for? Embark on an adventure along the Tuscan Via Lauretana. You won't regret it.

On The Map


Do it yourself

Ready to get going? Create and customize your own version of this adventure using the full Tour below as a template.

La Via Lauretana in Tuscany – full route

77.3 mi

6,700 ft

6,050 ft

Last updated: July 20, 2023

Plan your own version of this adventure in the multi-day planner based on the stages suggested in this Collection.

Learn more
komoot premium logo


  1. Map data © OpenStreetMap contributors

    Day 1: Siena to Sinalunga – la Via Lauretana in Tuscany

    37.4 mi
    9.0 mph
    3,175 ft
    2,950 ft
    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

    Forget the sea made of water: on the Via Lauretana from Siena to Cortona you pedal among the earthy waves of the Crete Senesi. The first of the two stages on this Tuscan route starts from Siena station. Pass by the two symbols of the city, the Cathedral of Siena and Piazza del Campo, and then leave the

    translated byView Original


  2. 04:33
    39.7 mi
    8.7 mph
    3,525 ft
    3,075 ft
    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

    Second day on the Tuscan Via Lauretana. From the village of Sinalunga today you can reach Cortona. But the journey is all that lies between a departure and an arrival, a mix of emotions, encounters, looks and thoughts, which in these lands are not long in coming. The difference in altitude of the day

    translated byView Original



Like this Collection?

Questions and Comments


Collection Stats

  • Tours
  • Distance
    77.1 mi
  • Duration
    08:41 h
  • Elevation
    6,675 ft6,025 ft

You Might Also Like

L'Eroica di Gaiole in Chianti – permanent route

Bike Touring Collection by Nicola Amadini

Seven dreamy day trips in Lech Zürs

Hiking Collection by Lech Zürs

Vecht Valley Route – a cross-border river landscape

Bike Touring Collection by Klaske Schep