Cycling in Tuscany: Your Guide to the Best Rides in the Region

Tuscany is one of the most beautiful parts of Italy, so it’s no wonder that many people like to ride bikes there. With its gentle hills, old towns, and countryside protected by UNESCO, cycling in Tuscany is a unique experience. The region boasts lots of great bike routes. From the hilly Chianti area and the Val d’Orcia to the awesome views from famous towns like Siena, Montalcino, and San Gimignano—each place has something nice to offer. 

What’s the best time for cycling?

Tuscan summers are usually hot and dry, while spring and autumn are milder but rainier. Winters may offer occasional sunny days but are generally wetter and colder, especially at night. So summer is ideal for those who enjoy the heat, while spring and autumn are typically the best seasons for cycling in Tuscany, offering pleasant weather and breathtaking countryside views.

Top Tuscany cycling routes

San Gimignano to Siena

Distance: 61.5 km with 1137 m elevation gain

Start your breathtaking cycling route to Siena from the north, San Gimignano. While there are two climbs initially, the reward comes with a splendid slow descent, offering unparalleled views of the Tuscan countryside as you make your way towards the charming historical village of Casole D’Elsa, offering captivating countryside views. A gentle descent leads you to the quaint town of Abbadia Isola, a notable stop along the Via Francigena Pilgrim walk. Once an overnight refuge for pilgrims in the 12th century, it now serves as a museum, preserving its rich history. Explore the fortified abbey, once a sanctuary for weary pilgrims en route to Rome.

Shortly after, you’ll encounter the majestic Monteriggioni castle, providing an ideal spot for a refreshing break. The route may become livelier as you approach Siena, but arriving from the north offers a quieter path into the city.

Mat and Angie Cycling along Via Francigena from San Gimignano to Siena – Best adventure in Tuscany
Siena and Chianti

Distance: 59 km with 1162 m elevation gain.

Starting from Siena, this charming cycling route winds through the picturesque landscapes of Tuscany, showcasing vineyards and some of the region’s most enchanting villages, including Castellina in Chianti and Radda in Chianti, nestled in the heart of the Chianti Classico region.

Along the way, you’ll encounter the medieval walled castle of Monteriggioni, adding a touch of history to your journey. As you depart Monteriggioni, the route becomes tranquil, leading you through a scenic climb to Castellina in Chianti’s historical center. Here, you’ll have the opportunity to indulge in a wine-tasting session at Castello di Fonterutoli. From Castellina, enjoy expansive panoramic views as you make your way to the historic village of Radda in Chianti. This quaint village exudes charm, with its narrow high street lined with unique shops, wine-tasting rooms, restaurants, and cafes.

Cigala Cycling Day 3 – Chianti, Tuscany Cycling Holiday
Val d’Orcia and Pienza

Distance: 37.7 km with 816 m elevation gain.

Embark on an easygoing journey with a gentle, gradual ascent to Montepulciano, where panoramic countryside views await. Upon entering Montepulciano, you’ll be transported back to the 15th century, as the town’s narrow streets bustle with local shops offering artisanal goods. Take a stroll to the main piazza for a refreshing coffee break and soak in the atmosphere. Continuing southward after Montepulciano, you’ll encounter a stretch of gravel roads, characteristic of Southern Tuscany, leading to the quaint village of Monticello. 

Monticello is nestled amidst picturesque surroundings and provides an idyllic setting for a delightful lunch break. Reservation is recommended, especially if you wish to dine al fresco on the balcony, offering breathtaking vistas on a sunny day. After a thrilling descent towards Bagno Vignoni, you’ll make your way back to Pienza via a brief climb.

Our Endless World TUSCANY Val D’Orcia | Pienza, Montepulciano, Montalcino
Lucca and Montecatini Terme

Distance: 39.1 km with 400 m elevation gain

Upon leaving Lucca, the countryside immediately unfolds before you. A must-see along the way is Villa Torregiani, one of Lucca’s most famous 16th-century villas at 12 km. It’s a stunning sight and a perfect photo opportunity.

As you cycle along Tuscany’s picturesque minor roads flanked by Cypress trees, you’ll pass numerous olive groves producing Lucca’s renowned olive oil. The route includes a short climb towards Montecarlo, the only one of the day. At 24 km, explore the medieval village of Montecarlo, where you can enjoy coffee or lunch in the main square. This is the only ascent of the day, and the medieval center of Montecarlo offers plenty of lunch options. On one side of this quaint hilltop village lies a landscape dotted with vineyards, while on the other side, you’ll find expansive olive groves. The vantage point from Montecarlo offers stunning countryside views, making it the perfect stop for lunch or a wine-tasting session. Arriving at 38 km, unwind in Montecatini Terme, a charming spa town known for its tranquil ambiance.

Cycling unboxed The Top 5 climbs you must do near Lucca
Island of Elba

Distance: 145.3 km with 3276 m elevation gain. 

The Island of Elba, though small, offers a captivating cycling adventure that can be completed in a single day. Starting from the picturesque Portoferraio after a short ferry ride from Piombino, mainland Tuscany, you’ll quickly realize that flat terrain is a rarity in Tuscany, and Elba is no exception. While Monte Capanne boasts the island’s highest peak, the route focuses on exploring the entire island rather than reaching the summit. Cyclists can cover all bases over three days and two nights, including Perone on the southwest side, ascending Monte Capanne. The journey begins by cycling halfway up Monte Capanne to Poggio before descending to the scenic coastal road along the island’s southwest side—the coastline, mainly through Pomonte.

The Island of Elba is so small you can ride the whole island in a day if you want to. You’ll take an hour ferry from Piombino on mainland Tuscany to Portoferraio with or without a car. If you have more than a day, you’ll discover some of the best beaches in Tuscany with the most transparent waters. Go early or late in the summer to avoid the crowds.

Pop Holidays Spectacular tour of the island of Elba by bike! Incredible landscapes!

Where to stay in Tuscany

Accommodation providers across Tuscany warmly welcome cyclists, as cycling is a popular sport in the region and a growing market. While there are no dedicated bike hotels per se, most hotels offer amenities such as bike storage and early breakfast options for cyclists. However, it’s important to note that mechanical assistance may not be readily available as these establishments are not specifically tailored to cyclists’ needs. Our favorites are:

Poggio All’Agnello: Web | Instagram

Il Ciocco: Web | Instagram

Hotel Minerva Siena: Web | Instagram 

Where to eat

Tuscany is great for discovering new food spots and visiting legendary eating points. While it is unlikely to find a dedicated cycling café, all owners will welcome your bike and you. We’d go for:

Buca di Sant Antonio: Via della Cervia 3, Lucca, Italy Web | Facebook

La Bandita Townhouse, Pienza: Corso Il Rossellino, 111, Pienza, Italy Web | Facebook

Bike rentals

Gippo Bike: Web | Instagram

Cicli Maggi: Web | Facebook

We always encourage your contribution to the guides. Got tips on cool trails, stories to share, or advice to give? Feel free to contact us anytime! We’re excited to enhance our guides with your valuable input. 

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