Italy by Bicycle-2023

Bicycling The Boot is a must-make trip at least once in a lifetime, but we offer tours in two diverse regions of Italy, because we’ve learned that one trip isn’t enough. Experience La Dolce Vita as you cycle past vineyards, through charming towns and along the sea, soaking in centuries of history and culture.

Our week-long tours — in storied Tuscany and Puglia, a favourite vacation spot for Italians and an emerging destination for foreigners — provide cyclists of all abilities with challenges and rewards in the form of stunning views, and yes, incredible food and drink.

Italy is a country bursting with heritage, be it cultural, culinary or architectural, which is why variety is a priority on our cycle tours in this remarkable destination.

Daily rides range from 20 to 70 kilometres as you cycle through olive groves and vineyards, along coastal roads and past walled villages. You’ll stop at cheese factories and hilltop monasteries, indulge in wine tastings and tour seaside caves, all the while meeting locals who are keen to share their stories with us. And we promise there will also be plenty of time for relaxing in the courtyard or poolside at the villas and B&Bs that you’ll call home.

Whether this is your first time to Italy, or one visit of many, we promise you’ll end the week with a new perspective on this beautiful country.