Cycling the Best Scenic Trails in Tuscany – History, Nature, and Coastal Adventures

Tuscany is a land of ancient history, rolling landscapes, and endless charm. Beyond its famous cities like Florence and Siena, the region’s countryside is a paradise for cycling enthusiasts. Here, hidden trails wind through medieval villages, vineyards, coastal paths, and unspoiled nature reserves. Cycling offers a unique way to explore these lesser-known treasures at your own pace while connecting with Tuscany’s rich cultural heritage.

What to expect when biking in Tuscany: rural trails and amazing scenery all around

This guide introduces some of the most captivating bike trails in Tuscany, offering a mix of history, nature, and adventure. Each trail highlights key stops, must-see points of interest, and essential details to help you plan your ride.

The northernmost corner of Tuscany, Lunigiana, is often referred to as the "Land of a Hundred Castles." This region, rich in medieval history, once served as a critical borderland between Tuscany, Liguria, and Emilia-Romagna. It’s a place where ancient castles and stone bridges dot the landscape, guarding stories of battles, pilgrimages, and trade routes.

Cycling through Lunigiana offers a deep dive into history, passing by rivers, lush valleys, and fortified towns. The route is perfect for those who love combining nature with cultural exploration.

Starting in Pontremoli, a medieval town rich in history, the route takes you past Castello del Piagnaro and the Museum of the Stele Statues before following a gentle ascent through rolling hills and oak forests. Arriving in Filattiera, you’ll find the Castello di Filattiera and the Church of San Giorgio, both reminders of the region’s medieval and religious heritage. The ride continues to Bagnone, a postcard-perfect village with a charming town square, castle ruins, and the soothing sound of the river below—an ideal spot to pause for a plate of testaroli. From here, the trail climbs toward Licciana Nardi, where the Castello di Licciana Nardi stands as a testament to Lunigiana’s noble past. Passing through the quiet hamlet of Tavernelle, once a key merchant settlement, the journey ends in Villafranca in Lunigiana, home to the Castello di Malnido, a fortress that once guarded ancient trade routes along the Magra River.

Points of Interest and Highlights

• Pontremoli: Explore the historic center, visit Castello del Piagnaro, and discover ancient stone sculptures at the Museum of the Stele Statues.

• Bagnone: Take a break in this tranquil village and visit the castle ruins perched on a hill overlooking the valley.

• Aulla: The Abbey of San Caprasio is a must-see, offering a glimpse into the region’s early medieval history.

• Villafranca in Lunigiana: Stroll along the river and enjoy a plate of testaroli, a local specialty served with fresh pesto.

Monte Argentario is a spectacular promontory in southern Tuscany, connected to the mainland by two sandy strips of land flanking the Orbetello Lagoon. This region, known as the Costa d’Argento (Silver Coast), offers some of the most breathtaking coastal landscapes in Italy. Once a key military outpost, Monte Argentario was fortified by the Spanish in the 16th century, leaving behind a network of watchtowers and fortresses that now serve as scenic viewpoints over the Tyrrhenian Sea.

Orbetello lagoon at sunset

This route takes cyclists on a stunning loop around Monte Argentario, offering dramatic coastal scenery, historical landmarks, and challenging climbs, making it ideal for those seeking both adventure and culture.

Beginning in Porto Santo Stefano, a vibrant coastal town with a bustling marina, the route ascends toward the Fortezza Spagnola, a fortress built in the 16th century to defend against pirates. From here, cyclists follow a panoramic road along the coastline, offering stunning views of the Tuscan Archipelago. The ride continues toward Porto Ercole, a charming fishing village once favored by the Medici family. Here, the Spanish-built Forte Stella, Forte Filippo, and Forte Santa Caterina stand as testaments to the area’s strategic past, each providing breathtaking viewpoints over the sea. The final stretch follows the Via Panoramica, a scenic road circling Monte Argentario, before returning to Porto Santo Stefano, where cyclists can unwind by the harbor and enjoy fresh seafood while watching the sunset over the water.

Points of Interest and Highlights

• Fortezza Spagnola (Porto Santo Stefano): A well-preserved 16th-century fortress offering panoramic views over the coastline.

• Porto Ercole: A picturesque harbor town where Caravaggio is believed to have spent his final days.

• Forte Stella: A star-shaped fortress positioned high above the sea, offering one of the best viewpoints on the coast.

• Forte Filippo & Forte Santa Caterina: Defensive fortifications with historic significance and stunning coastal scenery.

• Via Panoramica: A breathtaking road with sweeping views of the sea, the islands of Giglio and Giannutri, and the rugged cliffs of Monte Argentario.

The heart of Tuscany is known for its gentle hills, vineyards, and olive groves, and the towns of Peccioli and Montaione offer some of the best cycling experiences in this idyllic setting. Peccioli is a hidden gem, blending medieval charm with contemporary art installations, while Montaione is known for its proximity to the ancient pilgrimage site of San Vivaldo Monastery.

This cycling route takes riders through some of the most picturesque and culturally rich areas of central Tuscany, passing through medieval hamlets, historic churches, and panoramic ridge roads.

The journey begins in Montaione, a historic town with Etruscan origins, where cyclists head toward the Sacro Monte di San Vivaldo, a remarkable religious complex featuring chapels replicating the sacred sites of Jerusalem. From here, the route descends toward Iano, a village once known for onyx extraction, offering a spectacular vantage point over the surrounding countryside.

Continuing on, the trail leads to Castelfalfi, an ancient fortified village that has been beautifully restored, now featuring a wine estate and luxury retreat. Riding along cypress-lined roads, cyclists reach Villamagna, where the landscape becomes more rugged, transitioning into the wild, rolling hills typical of the Volterra region.

A scenic descent takes riders into Peccioli, a lively hilltop town marked by its striking bell tower and contemporary art installations scattered throughout the historic center. From Peccioli, the route climbs toward Montelopio and Fabbrica, two quiet medieval hamlets where time seems to have stood still. The final stretch passes through Legoli, home to an important 15th-century tabernacle frescoed by Benozzo Gozzoli, before looping back to Montaione.

Points of Interest and Highlights

• San Vivaldo Monastery: A sacred site known as the "Jerusalem of Tuscany", built in the 16th century.

• Iano: A former mining village offering spectacular views of the Tuscan landscape.

• Castelfalfi: A perfectly preserved medieval hamlet with a wine estate and castle ruins.

• Villamagna: A picturesque village on a panoramic ridge, marking the transition into Volterra’s rugged terrain.

• Peccioli: A charming town that blends medieval heritage with modern art installations and lively piazzas.

• Montelopio & Fabbrica: Two small villages offering a glimpse into rural Tuscan life and a quiet retreat from the main tourist paths.

• Legoli: A hidden gem featuring an important Renaissance fresco by Benozzo Gozzoli.

The Island of Elba, the largest in the Tuscan Archipelago, is a paradise for cyclists, offering a mix of coastal roads, rugged trails, and historical landmarks. This route crosses the central part of Elba from west to east, connecting the beach town of Procchio with the charming harbor of Porto Azzurro.

Riding through Mediterranean forests, panoramic ridges, and historic sites, cyclists will experience Napoleon Bonaparte’s country retreat, ancient windmill ruins, and the island’s renowned vineyards. The trail follows sections of the Grande Traversata Elbana (GTE), Elba’s famous long-distance hiking and biking route.

This MTB-friendly adventure offers a mix of paved roads and dirt trails, with some challenging climbs rewarded by breathtaking views of Portoferraio, Lacona, and the Gulf of Mola.

The ride starts in Procchio, a lively coastal village known for its sandy beaches and crystal-clear waters. After a short stretch along Provincial Road 25, the trail shifts onto the GTE route, leading into the Mediterranean scrub forestscovering the slopes of Mount San Martino. Here, a steady climb through pine and holm oak trees takes cyclists past Napoleon’s country residence, offering glimpses into his brief exile on Elba.

Reaching Buca di Bomba, the highest point of the trail, riders enjoy a panoramic view over Portoferraio before descending toward Mulino a Vento, where the ruins of an ancient windmill overlook both the northern and southern coasts of the island. The route then reaches Colle Reciso, a historic granite quarry, before following a winding dirt road down to Acquabona, an area known for its vineyards and Elba’s only golf course.

Passing through Buraccio, the trail enters Elba’s agricultural heart, where rows of vines and olive groves define the landscape. A final climb leads to Pontecchio, before a thrilling descent through rolling countryside brings riders to Porto Azzurro, a vibrant seaside town with a Spanish-built fortress and a lively harbor perfect for a post-ride aperitivo.

Points of Interest and Highlights

• Procchio: A coastal village with a wide sandy beach and turquoise waters.

• Mount San Martino: Home to Napoleon’s country residence, set amidst pine forests.

• Buca di Bomba: The highest point of the route, offering sweeping views of Portoferraio and Lacona Bay.

• Mulino a Vento: Ruins of an ancient windmill, providing a spectacular dual-coastline panorama.

• Colle Reciso: A historic granite quarry, once crucial to Elba’s economy.

• Buraccio & Pontecchio: An area of vineyards, olive groves, and family-run wineries producing Elba DOC wines.

• Porto Azzurro: A charming port town with a historic Spanish fortress (Forte San Giacomo), colorful waterfront, and excellent seafood restaurants.

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Tuscany is a true paradise for cyclists, offering a wide variety of landscapes and experiences. From ancient castles and medieval towns to coastal vistas and island adventures, the region’s trails provide something for every type of rider. Cycling allows you to experience Tuscany’s beauty up close—taking in its sights, sounds, and flavors at a relaxed, unhurried pace.

Whether you prefer rolling hills, historical routes, or coastal escapes, the trails in this guide are your gateway to discovering Tuscany’s hidden gems. So pack your bike, plan your route, and embark on an unforgettable adventure through one of Italy’s most beautiful regions.

What’s the best time of year to cycle in Tuscany?

The best time for cycling in Tuscany is from April to June and September to October, when the weather is mild, and the countryside is at its most vibrant.

Is it possible to combine cycling with sightseeing?

Absolutely! Many of the routes pass through towns and historical sites, allowing you to combine cycling with cultural exploration.

What type of bike is best for these trails?

For most trails, gravel or MTB is recommended due to varied terrain, although road bikes are suitable for coastal routes like the Costa d'Argento.

Are the trails suitable for intermediate riders?

Yes, most of the trails are designed for moderate-level cyclists. However, challenging sections like Monte Capanne on Elba may require a bit more experience.

Can I bring my bike to Elba Island?

Yes, you can easily bring your bike to Elba by ferry from Piombino. There are also rental options on the island for those who prefer not to transport their own bike.