11 gran fondo and ciclismo (cycling) events in Siena, Toscana

From big races to Saturday morning group runs—find gran fondo and ciclismo (cycling) events and connect with the local endurance sports community.

• Tuscany Crossing [finishers.com] - Facebook - Instagram
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  Fri, Apr 10, 2026

  Run Trail

  Siena, Toscana, Italy
  OpenStreetMap Google Maps
• Nova Eroica Buonconvento [finishers.com]
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  Sun, Apr 12, 2026

  Description

  Ready to embark on an epic adventure in the heart of Italian nature? 🌿 The "Nova Eroica Buonconvento" invites you to explore the magnificent Tuscan landscapes while challenging yourself with its road cycling routes. With distances ranging from 67 km to 290 km, there is something for every endurance level! 🏆

  Cycling

  Siena, Toscana, Italy
  OpenStreetMap Google Maps
• Tuscany Crossing [tuscanycrossing.com]
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  Fri, Apr 17, 2026

  14k 53k 103k 161k Run

  Via Del Cassero, Siena, Toscana, 53023, Italy
  OpenStreetMap Google Maps
• Crete Senesi Ultramarathon - Tuscany [creteultramarathon.it]
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  Sat, May 02, 2026

  5k 7k 15k 30k 50k Marathon Run Ultra

  35 Via Provinciale Sud, Siena, Toscana, 53040, Italy
  OpenStreetMap Google Maps
• Ultra Marathon des Crètes Senesi [finishers.com] [Register at creteultramarathon.it] - Facebook - Instagram
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  Sat, May 02, 2026

  Marathon Run Trail Ultra

  Siena, Toscana, Italy
  OpenStreetMap Google Maps
• Tuscany Moonlight [finishers.com]
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  Wed, Jul 22, 2026

  Run Trail Walk

  Siena, Toscana, Italy
  OpenStreetMap Google Maps
• Gran Fondo Strade Bianche [finishers.com] - Facebook - Instagram
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  Sun, Mar 07, 2027

  Description

  Ready to tread the paths of Tuscany 🌄 for a unique challenge? The Gran Fondo Strade Bianche awaits you with its legendary gravel routes that will give you an unforgettable experience! Choose between 93.3 km and 144.3 km to test your endurance on the famous Italian "white roads," amidst breathtaking landscapes 🏞️.

  Cycling Gran Fondo Gravel

  Siena, Toscana, Italy
  OpenStreetMap Google Maps