Tuscany Cycling Holidays

Tuscany Cycling Routes 2025

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

Chianti Classico

Chianti Classico is one of our best cycling tours thanks to your e-bike. The hilly terrain can be explore without exerting too much effort. Tasting wine in Chianti, visiting the towers of San Gimignano, taking in the views across the Val d’Esla and living the Italian way are all encouraged on this tour. Here are some of the route’s highlights.

Tour

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

Tuscany cycling holidays
Chianti Classico Tuscany cycle route

Val d Elsa

The Val d’Elsa is a highlight of Chianti Classico. Surrounded by ancient towns boasting thousands of years of history, there’s so much to see in this gorgeous area. This is what makes it it one of the best Tuscany cycling routes. Castellina, named for its magical castle, is a fabulous destination and filled with artisan shops waiting to be discovered. The area is actually known for its crystal glass production, so we highly recommend you take some souvenirs home.

Tuscany Cycling Holidays San Quirico to Asciano

Castellina to San Gimignano

This Tuscany cycling route takes in the very best and most famous scenery in the Chianti region. With panoramic views across the rolling vineyards whenever you stop, you begin your ride in an ancient, beautiful town and arrive in another stunning settlement. Fuel your pedalling with a traditional Tuscan lunch of fresh coffee and wood-fired oven pizza.

Tuscany Cycling Holidays Siena

Chianti

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 Monteriggioni. 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. Our favourite route to enjoy this wine region is from Radda to Gaiole, home to Brolio Castle which founded the Chianti Classico brand.

Chianti

Southern Tuscany Single Centre

There are plenty of Tuscan experiences to be had on our single centre tour. Make some bucket list-ticking memories on the shimmering roads and in the unforgettable towns of Montepulciano and Pienza. 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.

Tour

Explore the luxurious sights and flavours of Tuscany on this single centre tour. Through valleys and exciting cities, experience Italy like never before.

Tuscany cycling holidays
Tuscany Cycling Holidays Chianti Vineyards

Montepulciano

Roaming the Tuscan vineyards is a spectacular start to this cycling tour. Your destination is Montepulciano, a famed wine town where you must explore it’s rich wine heritage and taste a local blend while you’re at it. Surrounded by picturesque rolling terrain, Montepulciano 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

Val d’Orcia

The Val d’Orcia is a highlight of the Southern Tuscany. 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 Castello di Tornano to Siena

San Quirico d’Orcia to Bagno Vignone

The cycling tour has one of the bests routes on its first cycling day, with so many Tuscan delights along the way. Enjoy the cycling route from San Quirico d’Orcia to Bagno Vignone. Vast vistas characterise the day’s early riding before the final ride up to quiet Bagno Vignone before returning to your hotel. Be sure to spend a leisurely day exploring the thermal waters the town is known for and delve into the country’s storied past.

The Umbria Experience Tuscany Cycling Holidays

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

We Can Tailor-make
a Holiday to Suit You…

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.