Pedaling from Tuscany
to Umbria

A 6 day tour that crosses the province of Siena and Perugia offering typical Tuscan landscapes

starting from:

USD 3990

6 days

100 miles

200 km

3125 mt




Castiglion del Lago

Day 1

Arrival point at Chiusi train station. Transfer to the first hotel, in Sinalunga area, for check in and departure for the first bike ride with destination the village of Montepulciano, including a light lunch. Return to hotel via different itinerary. Overnight stay and dinner at the hotel.

  • 23 miles / 37 km
  • 650 mt
  • easy

Day 2

Departure for a second ride to the beautiful abbey of Monte Oliveto Maggiore, crossing the Tuscan countryside and climbing the hills between the villages of Trequanda, Chiusure and Asciano.Picnic lunch at Chiusure. Return to hotel via a different itinerary. Dinner in local restaurant.

  • 33 miles / 54 km
  • 1050 mt
  • sparkling

Day 3

Check out and departure by bike from Sinalunga to reach the village of Cortona. The ride crosses the Val di Chiana, a beautiful valley, famous for its beautiful Chianina cows that are specifically raised in the region. Easy to cycle, without too many difficulties and riding on quiet roads, crossing an area dedicated to agriculture including the picturesque village of Castiglion Fiorentino. Lunch in a local restaurant and dinner at the hotel's Michelin-starred restaurant.

  • 21 miles / 35 km
  • 320 mt
  • easy

Day 4

Departure from Cortona for a ride across the village first and then through the beautiful Tuscan countryside around, that will lead us to Lake Trasimeno in Umbria for just a few kilometres and then return back to Cortona, Tuscany by bicycle and / or support van. Lunch will take place at Villa Loggio winery, to taste local wines accompanied by a light typical Tuscan lunch of products such as cold cuts, cheeses, croutons etc. Dinner in a local restaurant in Cortona.

  • 34 miles / 55 km
  • 548 mt
  • sparkling

Day 5

Check out from Cortona and departure by bike for a ride all along the perimeter of Lake Trasimeno, passing first through the village of Tuoro, a historic place, where in 217A.C the famous battle of Lake Trasimeno took place between the Romans and the Carthaginians. Next visits include the villages of Passignano, San Feliciano and Sant'Arcangelo.

  • 37 miles / 60 km
  • 557 mt
  • easy

Day 6

Check out from hotel in Castiglion del Lago area and departure back home. A short morning ride is possible if you wish to depart in the afternoon instead. Pick up transfer to Chiusi train station, if needed, is available.

Select your tour


  • March 21 - 26

  • March 28 - April 2

  • April 4 - 9

  • April 11 - 16

  • April 18 - 23

  • April 25 - 30

  • May 2 - 7

  • May 9 - 14

  • May 16 - 21

  • May 23 - 28

  • May 30 - June 4

  • June 6 - 11

  • June 13 - 18

  • June 20 - 25

  • June 27 - July 2

  • July 4 - 9

This tour takes you to discover the Val di Chiana and Lake Trasimeno. A six day tour that crosses the provinces of Siena and Perugia, through typical Tuscan landscapes and medieval villages.
The stages of the tour develop on roads with less traffic and immersed into beautiful landscapes of the area.
The hotels are all 4 and 5 star relais hotels and the restaurants have been chosen amongst the most representative ones.

Keep in touch

Subscribe to our Newsletter

Copyright 2019 | Alterroads - Cycling & Leisure

made with by Web To Emotions