In this section, you can mix and match different routes to create a custom itinerary that fits your vision of Tuscany on two wheels. Though the rolling hills can be challenging, they are always rewarding—offering a unique sense of achievement and unforgettable emotions at every turn.
1. CHIANTI SKYLINES: FROM FLORENCE TO CASTELLINA
Crossing the heart of Tuscany, this route avoids major traffic hubs for a smooth departure from Florence toward the region’s most famous landmarks. The journey takes you through evocative settings: the terracotta workshops of Impruneta, the vineyards of Greve in Chianti, and the charming hilltop towns of Panzano and Castellina.
2. FOLLOWING THE EROICA FROM CASTELLINA TO SIENA
Steering away from the main tourist flows, this route explores the authentic soul of Chianti. The inland road connecting Radda and Vagliagli guarantees a seamless, low-traffic experience, unfolding across panoramic asphalt stretches where cycling history was made.
3. THE SIENA RIDGEWAY: DIRECT ROUTE FROM CASTELLINA
This segment provides a fast connection between Castellina and Siena via Quercegrossa, offering the most direct route to the city. Riding along the scenic ridge, you’ll enjoy a smooth flow and excellent visibility, with your gaze sweeping from the Chianti Classico vineyards to the unmistakable silhouettes of the Sienese lands appearing on the horizon.
4. A JOURNEY THROUGH HISTORY: CASTELLINA, RADDA, AND GAIOLE
This itinerary connects the three historic capitals of Chianti Classico — Castellina, Radda, and Gaiole — along a scenic hilltop road overlooking the entire region. By staying at elevation through dense woodlands and premium vineyards, the route avoids valley traffic, offering a total immersion in a timeless rural landscape.
5. SCENIC ROUTE FROM GAIOLE TO SIENA
This stage is a sequence of pure emotion: the ride is dynamic and fun, featuring fast, winding descents balanced by short, scenic climbs with spectacular views.
You’ll pedal along quiet backroads immersed in a landscape that alternates between the geometric patterns of vineyards and patches of Mediterranean woodland.
6. LE ONDE DELLA VAL D’ARBIA: DA SIENA A MONTALCINO
This stage is a sequence of pure emotion: the ride is dynamic and fun, featuring fast, winding descents balanced by short, scenic climbs with spectacular views.
You’ll pedal along quiet backroads immersed in a landscape that alternates between the geometric patterns of vineyards and patches of Mediterranean woodland.
7. ACROSS THE CRETE: FROM SIENA TO MONTEPULCIANO
Experience the transition from Chianti to the surreal, moon-like hills of the Crete Senesi. This route connects Siena to the Renaissance gem of Montepulciano, sticking to scenic secondary roads. You’ll cycle through the historic hamlet of Sinalunga before the final ascent into the heart of the Nobile wine country.
8. THE FORTRESS ROUTE FROM SIENA TO SAN GIMIGNANO
Set off with a fast, flowing section toward the medieval crown of Monteriggioni. After enjoying the steady flats, you’ll head down to Colle Val d’Elsa, famous for its crystal glass and ideal for a mid-ride pit stop. The final highlight is the scenic climb to San Gimignano: a consistent, rewarding ascent surrounded by white wine vineyards, leading you straight into the heart of this UNESCO world heritage skyline.
9. THROUGH THE VAL D’ORCIA FROM MONTALCINO TO MONTEPULCIANO
Ride through the heart of Tuscany’s most iconic landscape. After a technical descent from Montalcino to the medieval village of San Quirico d’Orcia, the path follows the rolling curves of the valley toward Pienza. This scenic stretch on secondary roads leads to the day’s final challenge: the climb to Montepulciano. It’s a demanding push among cypress trees and world-class vines, but the panoramic payoff at the top is truly unparalleled.
10. ABBEYS, CASTLES, AND SPA VILLAGES FROM MONTALCINO TO MONTEPULCIANO
This itinerary travels through the heart of the UNESCO heritage site, linking the two great wine capitals via historic hamlets and ancient abbeys. Descend from Montalcino into the sacred silence of Sant’Antimo, then climb toward the fortified skyline of Castiglione d’Orcia. The route touches the unique thermal pool of Bagno Vignoni and continues through the Renaissance lines of Pienza, concluding with the spectacular panoramic ascent to Montepulciano
11. . LANDSCAPE MIRRORS: FROM MONTEPULCIANO TO CORTONA
This itinerary glides down from the high vineyards of Montepulciano, crossing the wide Val di Chiana to reach the shimmering shores of Lake Trasimeno.
The route visits the charming lakeside village of Castiglione del Lago, featuring a fast, flat section along the water before heading toward the ‘natural balcony’ of Cortona. The final climb through silver olive groves concludes the journey with a panoramic view stretching from the lake’s surface to the majestic peaks of the Umbrian-Tuscan mountains.
12. . FROM TOWERS TO THE DOME, FROM SAN GIMIGNANO TO FLORENCE
Connect two of Tuscany’s most iconic skylines on this closing itinerary. After leaving San Gimignano for the historic streets of Certaldo, you’ll head back into the hills toward Montespertoli. Riding along scenic hilltop ridges, you’ll reach San Casciano for one last breathtaking view of the countryside before the final descent into the heart of Florence.
13. . FROM THE TOWERS TO THE SEA: FROM SAN GIMIGNANO TO MARINA DI CECINA
This itinerary descends from the Sienese hills toward the coast, traversing clay landscapes and dense Mediterranean scrub. The route first heads toward Volterra, the austere Etruscan city that dominates the region from its massive plateau.
From there, the road opens into a long, pleasant descent along the Cecina River valley, losing elevation toward the coastal plains. The journey concludes by passing through the town to reach the pine forests and beaches of Marina di Cecina, finishing directly on the shores of the Tyrrhenian Sea.
14. . GEOTHERMAL ENERGY AND METAL: FROM SAN GIMIGNANO TO FOLLONICA
This itinerary crosses the wild heart of Tuscany, linking the towers of San Gimignano to the Gulf of Follonica.
The route initially winds toward the rugged massif of Volterra, then immerses itself in the lunar landscape of Larderello, among boraciferous steam vents and geothermal vapors. It continues along the ridgelines of the Colline Metallifere until reaching Massa Marittima, a perched Romanesque jewel, before the final descent toward the pine forests and the sea of Follonica.
A route designed for experienced cyclists, marked by significant elevation gains and unique scenery ranging from underground steam to the deep blue of the Tyrrhenian Sea.
15. .FROM THE COAST TO LUCCA: PISA AND BEYOND
Travel from the shores of Marina di Cecina to the heart of Lucca. After a scenic ride along the Tyrrhenian coast, you’ll arrive at the leaning Tower in Pisa’s legendary Piazza dei Miracoli. From there, the journey shifts to the peaceful Serchio Greenway, a flat and scenic trail through the countryside that brings you straight to the historic ramparts of Lucca.