Tuscany bike tour, Florence, Siena, San Gimignano, winery

You Choose the Dates
Start your self-guided bike tour in Tuscany any day you would like, March through October (minimum two people).

Why Self-Guided?
Our self-guided Tuscany bike tours are for groups of two or more who want to explore Tuscany at their own pace. We provide detailed route notes, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates we take care of the details.

Self-Guided Bike Tours

» Self-Guided Florence to Siena Cycling
Price: US$ 550, 3 Days/2 Nights

This cycling adventure shows you the quiet beauty of the wine making region known as Chianti as you slowly pedal from Renaissance Florence to Medieval Siena. You tour a winery in a 15th century villa, explore two medieval fortified villages and dine on classic Tuscan cuisine.

» Self-Guided Florence to San Gimignano Cycling
Price: US$ 550, 3 Days/2 Nights

From the Renaissance splendors of Florence to the Medieval stone towers of San Gimignano, this three-day cycling adventure shows you the wonders of central Tuscany. Visit a winery and a fortified hilltop hamlet. Pedal through sun-drenched vineyards and olive groves on your way to Tuscany's prettiest hill town, San Gimignano.

» Self-Guided Siena Cycling
Price: US$ 900, 5 Days/4 Nights

Cycling from Florence to Siena you pedal through the heart of Chianti. Visit a 400-year old winery, explore a 13th Century castle, and tour the Renaissance gardens of an ancient abbey. This bike tour features beautiful cycling on Tuscany’s prettiest back roads.

» Self-Guided San Gimignano Cycling
Price: US$ 900, 5 Days/4 Nights

On this tour you see some of the most beautiful hill towns in Tuscany, including San Gimignano and Volterra. Tour a 16th Century winery, stay overnight in a Medieval village, marvel at stone towers, and visit a Roman amphitheater. The roads are peaceful and the landscape is quintessential Tuscan.

» Self-Guided Southern Tuscany Cycling
Price: US$ 900, 5 Days/4 Nights

When people think of Tuscany they think of Florence and its surroundings. Less touristy and equally beautiful is southern Tuscany. Stay overnight in the spectacular Tuscan hilltowns of Montalcino and Pienza. Explore a castle, tour a winery, and soak in a thermal hot spring.

» Self-Guided Tuscany Cycling
Price: US$ 1,600, 8 Days/7 Nights

Our longest self-guided bike tour takes you from Renaissance Florence through Medieval Siena on your way to Etruscan Volterra. See the prettiest hill towns of Tuscany at your own pace. Tour includes two winery visits and a non-cycling day in Siena for sightseeing. Nine day option available.