Cycling in Tuscany – Tuscany Explorer

Cycling in Tuscany – cycle through stunning Tuscan countryside, UNESCO World Heritage sites and ancient hilltop towns whilst tasting the finest local produce along the way. This extended tour includes five days cycling along some of the finest roads in Europe, through stunning vistas of cypress trees and Italian landscapes that haven’t changed in decades.

You’ll visit the iconic cities of Florence, Siena and Pisa, in addition to several spectacular hilltop towns including Volterra, Montepulciano, Sa Quirico D’Orcia and Montelcino.

Please scroll to the bottom of this page to view our open trips, or alternatively get in touch if you have a small group of people who may be interested.

Adventure Facts

  • Duration:

    8 days
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Experience the finest of Tuscan scenery and culture by bicycle! Ride through the stunning landscapes of Tuscany, through impressive ancient hilltop towns and vineyards, along some of the most romantic and evocative roads in Europe. This trip combines the perfect balance of fantastic cycling with a dazzling array of cultural and culinary delights unique to this incredible region of Italy.



  • The UNESCO world heritage sites of Florence, San Gimignano, Siena and Pienza
  • Cycling through the unique Val D’Orcia region
  • Visiting the legendary architectural and cultural sites of Florence and Siena
  • Learning about and tasting the numerous wines and other produce of the region
  • Soaking in the sights, sounds and smells of the Tuscan countryside
  • Visiting the iconic Leaning Tower of Pisa

Pricing, Dates & Availability

  • Cycling in Tuscany – Tuscany Explorer
    5th October 2024 - 12th October 2024
    12 places left


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