Bicycle holidays in Tuscany: routes, tips, and must-see destinations
Tuscany has always been a land of cyclists, rich in landscapes that constantly change: from the Apuan Alps to Versilia, from the Tuscan-Emilian Apennines down to the south in Maremma, passing through the Island of Elba, a paradise for bikers with breathtaking views.
Discover the best routes
1. Via Francigena with fifteen stages all to discover, crossing 38 municipalities and stretching 380 km, Via Francigena is undoubtedly one of the most fascinating and important routes in Tuscany. In the past, the route was not only used for religious purposes but people used to make the "slow" journey to interact with the communities along the Via Francigena. Among the most beautiful sections to ride is San Miniato - Gambassi Terme (24km), considered particularly scenic as it winds through the hills of Val d'Elsa offering breathtaking views. Don't miss the Gambassi Thermal Baths, famous for their thermal waters where you can relax before getting back on the saddle.
2. Via degli Dei is a hiking route connecting Bologna and Florence through the Apennines, retracing the medieval paths used for communication between Bologna and Florence. The route, between 110 and 120 km depending on the path taken, crosses numerous places of natural and scenic interest. We recommend using an MTB because some sections cross mountain trails mixed with dirt roads featuring challenging elevation changes.
The journey usually takes two days. We recommend tackling the route well-trained and with suitable equipment.
3. Percorso Permanente Eroica stretches for 209 km in the heart of the Terre di Siena, passing through Chianti, the Crete Senesi, and Val d'Orcia, showcasing some of the most beautiful landscapes the world envies us for.
The route is characterized by continuous transitions from paved to dirt roads with a total elevation gain of 3800 meters.
The journey can start from any point along the route.
Every affiliated business is recognized as a start and finish point of the circuit and is authorized to issue stamps.
The stamps are used to complete the Road Book that certifies passage through the 5 control zones of the circuit: Chianti - Siena and Val d'Arbia - Montalcino - Val d'Asso - Crete Senesi.
The route can be done year-round and with any bike.
4. Island of Elba by bike features steep climbs, drops overlooking the sea, and a succession of breathtaking panoramas in contact with nature and surrounded by the sea.
Everyone can discover the Island by bike: mountain biking on forest trails, road biking following mule tracks.
The various itineraries allow you to encounter always different trails, making each excursion unique.
5. Arno Cycle Path runs entirely in Tuscany through the provinces of Arezzo, Florence, and Pisa, featuring multiple sections of naturalistic, historical, artistic, and cultural interest.
The first section with places like Stia and San Giovanni Valdarno, Figline, Incisa, and Pontassieve stands out for great natural and landscape attractions. Florence and Pisa bring cyclists directly into the heart of the world’s most famous art cities.
The total length is about 270 km and it is one of the most beautiful cycle paths in Italy.
6. Val d'Orcia if you decide to visit Tuscany by bike, you must not forget to visit this part of the region that has inspired writers, poets, and artists due to its vast, sparsely populated territory, cycling through its famous villages including Montalcino and Pienza, up to the vineyards of Brunello di Montalcino.
7. Maremma offers numerous routes to discover this fantastic part of Tuscany with multiple itineraries suitable for all types of bicycles. This part of Tuscany is rich in breathtaking landscapes, long trails, dense woods crossing the Mediterranean scrub with many ups and downs, leading to splendid medieval villages and cliffs overlooking the sea where you find famous coves and stunning cliffs.
In Maremma, you can ride on over 30 routes to explore one of Italy’s most beautiful territories between sea and unspoiled beaches.
Food and culture along the routes
A cycling holiday in Tuscany is not just about sport, but also a journey through flavors and traditions. You can stop to taste a glass of Chianti Classico, sample the extra virgin olive oil from the Tuscan hills, or enjoy typical dishes like ribollita and pappa al pomodoro.
Cultural stops are equally unmissable: visit Siena with Piazza del Campo, admire the Leaning Tower of Pisa, walk through the alleys of San Gimignano, or discover the Cathedral of Florence.
When to go on a bike holiday in Tuscany
The best periods are spring (April-June) and autumn (September-October), when the climate is mild and the colors of nature are at their peak. Summer is perfect for Maremma and the coast, but you need to start early in the morning to avoid the heat.
Why a cycling holiday in Tuscany is unique
Cycling in Tuscany means experiencing the region authentically: not just crossing it, but savoring it slowly, stopping when a view moves you or when a small village invites you in. It’s a way to travel sustainably, stay fit, and collect unforgettable memories.
If you love cycling and want to combine sport, culture, and good food, Tuscany is the perfect destination for your next holiday. Whether you choose a weekend or a multi-day tour, you will find routes suitable for every level and a hospitality that will make the trip special.
From Florence to the Chianti hills, from Maremma to Via Francigena, Tuscany awaits you to be discovered pedal by pedal.
Setting off on a bike trip requires proper athletic preparation and a basic mechanical knowledge to be ready to solve any bike problems that may occur during the journey. With the tips from our mechanics, you can start with peace of mind.
Tuscany: Beautiful Everywhere