Tuscany's Legendary Gravel Routes

Day 1: Pienza - Bagno Vignoni - Pienza
15 mi / 25 km

This cycle adventure begins in Pienza, a UNESCO World Heritage site in Tuscany's Val d'Orcia. Often dubbed the "perfect town," it’s celebrated for its Renaissance architecture and cobblestone streets.

Following a brief welcome meeting and bike fitting, set off on the first ride to Bagna Vignoni, a historic thermal spa town with therapeutic hot springs. The town features a large rectangular pool in Piazza delle Sorgenti dating back to Roman times, surrounded by medieval buildings and the Madonna di Vita Leta chapel.

Elevation gain: +558m
Surface: 8 mi. gravel / 7 mi. asphalt

Day 2: Pienza - Montepulciano - Monticchiello - Pienza
32 mi / 51 km

Embark on a cycling adventure from Pienza today. Pedal through cypress tree-lined paths, recalling scenes from films like Gladiator and The English Patient. Explore off-the-beaten-path gravel tracks and take a moment to enjoy an espresso at La Foce, overlooking the conquered routes. Continue your journey to Montepulciano, celebrated for its Renaissance architecture and renowned as a prominent wine-producing region, especially known for the Vino Nobile red wine. On your way back to Pienza, make a stop in the village of Monticchiello, a quintessential Tuscan hill town.

Elevation gain: +872m
Surface: 21 mi. gravel / 11 mi. asphalt

Day 3: Pienza - Montalcino
25 mi / 41 km

The best route to travel from Pienza to Montalcino includes Eroica sections Lucignano d'asso and Pieve A Salti. Depart from Pienza, covering 3 mi. on a paved road before turning onto a white road towards Cosona and arriving at the hamlet of Lucignano – a stop at the local emporio for an espresso is a must. After a short ride on the paved road, transition to the Eroica gravel section Pieve a Salti, offering a picturesque rural landscape with 6 mi. of undulating terrain. Reach Buonconvento by lunchtime, and prepare for the ascent to Montalcino, part paved and part gravel, passing through vineyards and wineries. Upon reaching Montalcino, a visit to the fortress is highly recommended to enjoy the breathtaking view of the traversed valley.

Spend the evening in Montalcino with its medieval charm, ancient architecture, and world-famous Brunello di Montalcino wine.

Elevation gain: +855m
Surface: 15 mi. gravel / 10 mi. asphalt

Day 4: Montalcino - Siena
37 mi / 59 km

L'Eroica, meaning "The Heroic," is an annual celebration of cycling's golden age. Held every October, thousands of dedicated cyclists transport themselves back in time to tackle gravel roads using vintage bikes of the past. Today, you’ll experience your own journey into cycling's heroic origins by riding one of L'Eroica's stunning gravel sections in the heart of Brunello di Montalcino, Tuscany's renowned wine region. Starting at Castiglion del Bosco, the largest Brunello winery and farm owned by the famous Italian fashion designer Ferragamo, you'll navigate through Passo del Lume Spento, Bibbiano, La Piana, and Murlo, encountering legendary Eroica sections with steep yet brief ups and downs. Ville di Corsano provides a perfect spot for a light lunch before the final 7 mi. along a secondary paved road to Siena.

Explore Siena with its historic UNESCO World Heritage Site center, offering a blend of art, history, and distinctive Tuscan charm.

Elevation: +1015m
Surface: 16 mi. gravel / 21 mi. asphalt

Day 5: Siena - Gaiole
or Gaiole in Chianti (29 mi / 47 km

Today's destination is the town where the Eroica cycling event begins. Following breakfast, venture into the enchanting Chianti region, leaving Siena through an Eroica gravel section at Pieve a Bozzone and Vico d'Arbia. Traverse wheat fields before entering the celebrated vineyards of Chianti Classico. Covering approximately 9 mi., reach Pianella and embark on a scenic journey through Canonica A Cerreto and Vagliagli, exploring the charming Chianti Classico vineyards with castles and hilltop hamlets. Arrive in Radda in Chianti for lunch after a 23 mi. ride, mostly on gravel roads.

Conclude the day in Gaiole. Explore the town center, indulging in authentic Tuscan cuisine, strolling through picturesque streets, and sampling regional wines in a local wine bar.

Elevation: +923m
Surface: 21 mi. gravel / 8 mi. asphalt

Day 6: Gaiole - Castello di Brolio - Gaiole
34 mi / 54 km

Today is dedicated to exploring all the villages and hamlets of Chianti Senese. Begin your journey from "Castle di Spaltenna" in Gaiole and reach Castello di Brolio where a coffee awaits at Agribar in front of the winery, a popular spot for cyclists and locals alike. Proceed through a short gravel section of Eroica before navigating very secondary roads to Castelnuovo Berardenga, providing numerous lunch options. Back on your bike, visit other small villages like San Gusmé and Villa a Sesta before returning to Brolio. To reach Gaiole, opt for the easier downhill road or the challenging uphill route to Castagnoli, followed by a descent to Castello di Meleto.

Elevation: +1013m
Surface: 7 mi. gravel / 27 mi. asphalt

Day 7: Gaiole - Badia a Coltibuono - Gaiole
13 mi / 21 km

The tour ends today. If time allows and you’d like one last adventure, consider cycling the short loop to Badia a Coltibuono, a historic abbey surrounded by vineyards and olive groves.