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The Best Cycling Routes in Tuscany

22nd October, 2022

Tuscany is an ideal destination for cyclists looking to explore beautiful landscapes, indulge in delicious Italian cuisine, and immerse themselves in historic sites. With its stunning mountain trails and rolling hills of vineyards and olive groves, Tuscany has something to offer cyclists of all levels. Come discover the best cycling routes in the region.

Countryside Route Through Chianti

Cycle through the famed Chianti region, a dreamy countryside dotted with sunflower fields and fairy-tale castles. Start in Castellina in Chianti and head north to Radda in Chianti. Taste some of Italy’s best wines as you go, with stops at local wineries en route! Along the way, enjoy the views of rolling hills, stone villages and some of the area’s most impressive medieval architecture.

Heart Shaped road through an Italian Vineyard

Heart Shaped road through Chianti

Le Strade dei Vini e dell’Olio (Roads of Wine and Oil)

Test your cycling skills on the rolling hills of the “Roads of Wine and Oil”. This route kicks off near Florence, following bicycle paths along roads lined with vineyards and olive groves. Keep an eye out for the iconic colors of the Tuscan countryside: blue skies, green olive trees, and yellow fields of sunflowers! Enjoy breathtaking views as you make your way through historic towns such as San Gimignano and Montalcino. Bon voyage!

Siena to Colle Val d’Elsa

Discover this beautiful route from the historic city of Siena that leads you through the breathtaking Val d’Elsa countryside. The stretch from Siena to Colle Val d’Elsa is around 28 miles with few notable hills and ends in one of Tuscany’s pleasant hamlets, boasting picturesque views for much of the route.

San Gimignano to Greve in Chianti

Another must-do cycling route and one of the most beloved trails in Tuscany, the San Gimignano to Greve in Chianti route offers riders stunning landscapes that meander through wine country. A moderate 27-mile stretch, you will pass beautiful vineyards and olive groves as you make your way for a taste of sumptuous Chianti wines at Giacomo Mori Winery – one of Italy’s oldest wine estates!

The Towers at San Giminano (1)

The Towers at San Giminano

The Strade Bianche Gran Fondo Tuscany

An annual event bringing cyclists from all over the world and traversing some of Tuscany’s most beautiful and off-the-beaten-tracks sceneries, the Gran Fondo Strade Bianche let you experience the region just like a professional cyclist. Starting at Piazza del Campo in Siena, this 128-mile classic route travels through picturesque medieval villages, steeply undulating roads, picturesque vineyards, white gravel trails and a variety of challenging climbs from hill town to hill town.

The Strada Bianche Sportive

The Strada Bianche Sportive