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Cycling Routes in Tuscany and Umbria

Posted 01 Sep 2021

Cycling in Tuscany and Umbria 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 things that are most important 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 Tuscany and Umbria's best cycling routes and what you can expect along the way. 

Tuscany Cycle Routes

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.

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Tuscany cycle routes

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.

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Tuscany cycling routes

San Quirico to Asciano

This gentle ride 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.

View our Tuscan Experience tour

Tuscany cycle routes

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. Ride 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 bike ride, see out the remains of the day on a sun-soaked piazza with a glass of the region’s famous full-bodied tipple

View our Tuscan Experience tour

Tuscany cycling routes

The Day I Saw Siena 

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. 

View our The Day I Saw Siena tour

Tuscany cycling routes

Greve

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.

View our The Day I Saw Siena tour

Tuscany cycle routes

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. 

View our The Day I Saw Siena tour

Tuscany cycling routes

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. 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.

View our The Day I Saw Siena tour

Tuscany cycle routes

The Umbrian Experience

The Umbrian Experience takes you on a seven-day odyssey through some of Italy’s most incredible riding. This tour is a true culinary exploration of Umbria and includes some of the best accommodation we have to offer. With your luggage being transported between each destination, you can spend the day on your e-bikes sampling the best riding, food, and wine of the region as we take care of your needs. 

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Tuscany cycling routesCortona to Montone

If castles and coffee are your thing, this cycling route into Umbria is ideal for you. Tours of the traditional and historical Tuscan castles that are found in the Niccone Valley are a highlight of the day’s ride. Stop off for a revitalising coffee en route through the Upper Tiber Valley before coasting on sleepy country roads to the medieval village of Montone. Once there you can travel back through time as you explore the tight streets before feasting on an Umbrian spread in the evening. 

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Gubbio to Assisi

The cycling route from Gubbio to Assisi makes the most of your e-bike power. Instead of struggling through the Apennines, you will reach this Umbrian haven on the Via Flaminia with relative ease. Be sure to stop off on the way and sample the Roman ruins on the route, as well as enjoying some of the energy-boosting pasta dishes that the region is best known for.

Once in the cobbled streets of medieval Assisi, make sure to swap the pasta for the tenderness of a Florentine T-bone steak, washed down with the local red of course. The town is the birthplace of Italy’s patron saint, Saint Francis of Assisi, and the gothic Basilica that takes his name still dominates the skyline. This UNESCO World Heritage Site is home to a series of beautiful frescoes and a crypt where you can visit Francis himself.

Tuscany and Umbria have long been bucket list destinations for holiday-makers the world over. If you’re of the outdoorsy persuasion, keen for the fresh air that everyday life can’t always provide, you can’t do better than an e-bike tour.

View our Umbria Experience tour

Tuscany cycling routes

For more recommendations on the best cycle routes in Tuscany and Umbria, give us a call on 020 7471 7760, or alternatively, view our cycling holidays in Tuscany and Umbria here.

View all our Tuscany cycling holidays here

View our Umbria cycling holidays here

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