Self Guided Walking Holidays & Cycling Holidays


Classic Tuscan landscape with Cyprus trees and winding road

Tuscany Cycling

Cycling Holidays in Tuscany

Cycling in Tuscany will allow you to immerse yourself in (arguably) the most dramatic and passionate region of Italy. Bike on quiet roads over rolling hills through the heart of Tuscany. Gorgeous golden hillsides, rich artistic heritage, gentle biking paths and great food and wine at the end of a day’s cycling make this tour a perfect mix of what makes Tuscany great.

Choose the best cycling in Tuscany tour for you; from cycling Tuscany: Chianti & Siena, Florence to Montepulciano or Pisa to Florence, our tours are sure to offer an authentic Italian experience on two wheels. With our wide range of cycling tours in Italy, we are sure you will be returning again soon. 

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Tour of Tuscany: Florence to Montepulciano

Take on our Tour of Tuscany cycling from Florence, through the world-class winelands of Chianti and Montepulciano.

Duration: 8 days 7 Nights
Available: May - October
From £945.00

Tuscany: Pisa to Florence Cycling

Discover quintessential Tuscany on two wheels. From the world-famous city of Pisa and its iconic tower, you pedal through the Tuscan landscape, past scented vineyards and verdant olive groves towards Florence: birthplace of the Renaissance and city of timeless beauty.

Duration: 7 Days & 6 Nights
Available: March - December
From £525.00

Cycling Tuscany: Chianti & Siena

Experience the very best of classic Tuscany on a self guided cycle tour. Take to two wheels and cycle bella Italia, discovering picture-postcard Medieval and Renaissance hill-top villages as well as must-see Siena, accompanied by sumptuous cuisine and the famed Chianti, Brunello and Nobile wines.

Duration: 8 Days & 7 Nights
Available: March - Early November
From £1045.00

Road Cycling: Florence to Siena

Ride from Florence to Siena through the heart of Tuscany’s Chianti postcard perfect wine region.

Duration: 5 days 4 Nights
Available: May - October
From £495.00
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Book self-guided walking holidays and cycling holidays with Macs Adventure. Explore Europe, the UK and the rest of the world on our walking holidays and cycling holidays, and find out why thousands of people trust us to arrange their perfect self-guided adventure.


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