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Tuscany Cycling Holidays

Tuscany Cycling Routes

Explore our favourite Tuscany cycling routes, linking medieval villages, picturesque vistas and beautiful cuisine.

Cycling in Tuscany is quite unlike any other experience on two wheels. With picturesque cycling routes, beautiful cuisine and movie-worthy medieval hamlets, it’s one of the most beautiful regions in the world and is home to some of its best cycling.

The famous cypress tree-lined white roads are a haven for any rider, but we think they’re perhaps best travelled via e-bike. This way you can explore the most important things without having to blow a gasket to do it. Cruise with electric ease and soak in the stunning views, delicious culinary delights, and luxurious accommodation of our tours at your own pace. Here are some of the best cycling routes in Tuscany and what you can expect along the way.

Tuscany E-Bike Cycling Holidays

The Tuscan Experience

The Tuscan Experience is one of our most popular cycling tours and thanks to your e-bike. The hilly terrain can be explore without exerting too much effort. Tasting wine in Chianti, visiting the Abbey of Sant’Antimo, taking in the views across Lake Trasimeno and living the Italian way are all encouraged on this tour. Here are some of the route’s highlights.


Take in the stunning countryside of Tuscany on this tailor-made e-bike tour through spectacular Tuscan valleys.

Tuscany cycling holidays
Tuscany Cycling Holidays Val d'Orcia

Val d’Orcia

The Val d’Orcia is a highlight of the Tuscan Experience. Cinema-goers may recognise the green and gold rolling fields from scenes in films such as Gladiator and Hannibal. Your e-bike will make light work of the climbs, leaving you with ample energy in reserve to enjoy the Brunello wines and local-made pecorino cheeses that characterise the area’s cuisine.

Tuscany Cycling Holidays San Quirico to Asciano

San Quirico to Asciano

This cycling route takes in the very best and most famous views in Tuscany. With panoramic views across the rolling vineyards whenever you stop, you will follow the famous pilgrimage route along the Via Francigena. Then fuel your day’s ride in Asciano with a proper Tuscan lunch of fresh coffee and wood-fired oven pizza.

Tuscany Cycling Holidays Siena


What better way is there to toast a day in Tuscany than with a glass of Chianti? Especially after exploring the region that gives these famous wines their name. Cycle through the wooded valleys and rolling countryside before doing what the Italians do and enjoy a mid-morning coffee in medieval Radda. Once you’ve finished your cycle ride, see out the remains of the day on a sun-soaked piazza with a glass of the region’s famous full-bodied tipple.

Tuscany Cycling Holidays Chianti

The Grand Tour of Tuscany

There are plenty of Tuscan experiences to be had on our Siena guided tour. Make some bucket list-ticking memories on the shimmering roads and in the unforgettable Chianti towns of Greve and Lecchi. Marvel at the scenery from your e-bike and jump off to explore the area’s rich history while soaking up the quintessential Tuscan atmosphere.


Explore the luxurious sights and flavours of Tuscany on this self-guided cycling tour. Through valleys and exciting cities, experience Italy like never before.

Tuscany cycling holidays
Tuscany Cycling Holidays Chianti Vineyards


Roaming the Chianti vineyards is a spectacular start to this cycling tour. Satisfy your art fix in Vignamaggio, the rumoured setting of Leonardo Da Vinci’s Mona Lisa, and taste a local blend while you’re at it. Surrounded by picturesque rolling terrain, Greve and its unique piazza will be far easier to visit with the climb-levelling power of your e-bike. While you’re there, don’t miss the cavernous cellars filled floor to ceiling with local meats and cheeses.

Tuscany Cycling Holidays Castello di Torano Greve

Castello di Tornano to Siena

The jewel of the region is also one of the capitals of Italian cycling. Home to the finish of Strade Bianche in its magnificent central Piazza del Campo, Siena is a haven for touring cyclists. Unlike in the race, you will make light work of the town’s steep climb and surrounding hills thanks to the assistance of your e-bike. This means there is plenty of time to explore Siena and stop for a bite to eat at lunch – Norcia black truffles with some cured meats perhaps. 

Tuscany Cycling Holidays Castello di Tornano to Siena

San Gimignano to Volterra

The cycling tour arguably saves the best experience for its final day, which may be hard to believe with so many Tuscan delights along the way. Enjoy the cycling route from San Gimignano to Volterra. Vast vistas and a long descent characterise the day’s early riding before the final ride up to quiet Volterra. Be sure to spend a leisurely day within these eighth-century walls and delve into the country’s storied past with a visit to the spectacular Roman ruins.

The Umbria Experience Tuscany Cycling Holidays

For more recommendations on the best cycle routes in Tuscany, give us a call on 020 7471 7760.

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We have a team of experts on hand to help you choose the perfect holiday. From a luxury cycling holiday weekend in Tuscany to a big adventure in through the Loire Valley, we’re whatever you want your holiday to be.