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Pedaling under the Tuscan sun

Holiday packages

A 6 days experience to discover Cortona, Montepulciano, Pienza, Montalcino and the Val d'Orcia by bike

by  Cicloposse

The mystique of this land lies not only in its landscape but also in its nature, vineyards, and history. Oak woods, olive groves and vineyards adorn enchanting hillsides alongside medieval villages and historical monuments. The journey culminates gloriously in Siena.

Itinerary highlights:

  • Learn about the rich history of Cortona, the land of the Tuscan sun.
  • Explore the medieval hilltop villages of Tuscany, each uniquely beautiful.
  • Enjoy scenic cycling through the stunning landscape of the Val d’Orcia.
  • Experience the stark and alluring lunar terrain of the Crete Senesi region.

Prices include

  • Six nights in excellent four & three-star superior hotels
  • Six breakfasts
  • All luggage transfers
  • RideWithGPS App: tracks, route notes, off-line navigation
  • Trip notes: sightseeing & meals suggestions
  • Maps with elevation gain
  • Delivery bike at Cortona hotel & bike fitting
  • Pick-up of bikes and gear in Siena
  • Keepsake cicloposse water bottle
  • Sales taxes

Supplemental charges

  • Bike rental for the entire tour: Hybrid bike (euro 180) or Race bike, Gravel, e-Bike (euro 240)

Meeting point



  • Day 1: Meeting in Cortona & bike fitting
  • Day 2  - Lago Trasimeno

Ride to Valle di Pierle and his Rocca - Total distance: 50 kilometres / 31 miles

  • Day 3 Montepulciano & Pienza

Ride from Cortona to Pienza via Montepulciano and through vineyards.
This splendid little town is called "the Pearl of the Cinquecento". Pienza is also famous for the delicious sheep milk cheese pecorino.
Distance: 63,5 kilometres / 39,5 miles 

  • Day 4 - Val d’Orcia and Radicofani

Circular bike ride into Val d'Orcia - Total distance 63,8 kilometres / 39,8 miles 

  • Day 5 - Montalcino & Brunello wine

Pause in the fairy-tale village of Bagno Vignoni. The wine town of Montalcino is the highlight. Visit the fortress to enjoy a breathtaking view of the entire valley you've just biked through
Distance 44,4 kilometres / 27,7 miles  

  • Day 6 -  Monte Oliveto & Siena

Cycle from Montalcino to Siena via Monte Oliveto Maggiore and Asciano. Visit Piazza del Campo, Torre del Mangia and the famous Duomo
Distance 56,7 kilometres / 35,5 miles


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