Meet and greet in Pienza, the purest Renaissance town in the world, for a welcome and bike fitting. Known as the "perfect town," Pienza is a remarkable example of Renaissance-era town planning. For those with even a slight appreciation for beautiful architecture, strolling around its cobblestone streets is a delight. The first short bike ride will take you to Bagno Vignoni, a thermal spa town dating back to Roman times, and the Madonna di Vitaleta Chapel.

• Daily distance: 25 km / 15 miles
• Elevation gain: +558 m / -565 m
• Ground: 12 km asphalt and 13 km gravel
• Accommodation: Relais Il Chiostro di Pienza

To get from Pienza to Montalcino, you'll ride on sections of the Eroica route called Lucignano d'Asso and Pieve a Salti. Leaving Pienza on 6 km of paved road, you will take an un-paved road toward Cosona and reach the quaint hamlet of Lucignano—an espresso at the little emporio is highly recommended. Once you reach the paved road, it's just one km before you start the next Eroica gravel section, Pieve a Salti, which offers stunning landscapes. It's a 9 km journey up and down through the rural countryside, arriving in Buonconvento around lunchtime. Then, you face the climb to the famed wine town of Montalcino, a total of 10 km: 5km on paved and 5km on gravel roads, all through vineyards and wineries. Once in town, we strongly suggest visiting the fortress to admire the breathtaking view of the valley you've just biked through.

Tonight, at the included dinner, reward yourself with at least a glass of Brunello—we'll share a list of our favorites.

• Daily distance: 41 km / 25 miles
• Elevation gain: +855 m / -807 m
• Ground: 17 km asphalt and 24 km gravel
• Accommodation: Hotel il giglio or Vecchia Oliveira in Montalcino
• Meals: Breakfast, Dinner

Today, we propose the original loop of the Eroica Montalcino route, known as "del Brunello." This epic loop around Montalcino takes you on the side facing the sea. Ride on gravel roads through grape fields, passing through Tavernelle, Sant’ Angelo in Colle, and Castelnuovo dell’Abate. Very close to the latter, you can find the Sant'Antimo Abbey, a unique site with more than 1000 years of history, significant to Montalcino and the entire Val d’Orcia area. The final climb to return to Montalcino town is, once again, through vineyards. A wine tour and tasting are included.

• Daily distance: 45 km
• Elevation gain: +908 mt / -908 mt
• Ground: 24 km asphalt and 21 km gravel
• Accommodation: Hotel il giglio or Vecchia Oliveira in Montalcino
• Meals: Breakfast

L'Eroica—meaning "The Heroic"—celebrates the golden age of cycling. This event occurs every October, drawing thousands of dedicated cyclists who travel back in time to ride these gravel roads on vintage bikes. Equipped with heavy lugged-steel frames, down-tube shifters, and challenging gear ratios, these bikes are a testament to the participants' hardman mentality, often complemented by red wine in their water bottles.

Today, we'll experience a slice of cycling's heroic past as we embark on one of the most picturesque gravel sections of L'Eroica from the heart of Brunello di Montalcino, Tuscany's most renowned wine region. We start our ride at the top of Passo del Lume Spento and proceed to the Castiglion del Bosco gravel section. Castiglion del Bosco, the largest Brunello winery and farm, is owned by Ferragamo, the famed Italian fashion designer. After reaching Bibbiano, we continue to another beautiful section called La Piana, and then to Murlo, where we’ll stop for a café and visit. Soon, you'll tackle another legendary Eroica section to Radi, featuring some steep, short ascents and descents. At Ville di Corsano, a light lunch awaits. From here, it's the last 12 km on a secondary paved road to Siena.

• Daily distance: 58,5 km / 36 miles
• Elevation gain: +1015 m / -1229 m
• Ground: 32 km asphalt and 24 km gravel
• Accommodation: Hotel Villa str in Siena
• Meals: Breakfast

Today, our destination is the town where L'Eroica begins. After enjoying a gourmet breakfast, set out into the magical Chianti region. You will exit Siena via the Eroica gravel section, Pieve a Bozzone, and Vico d'Arbia, making your way through wheat fields before reaching the vineyards of this celebrated wine region. After 15 km, you will arrive in Pianella. From here, embark on a long and glorious section to Canonica A Cerreto and Vagliagli—all roads through Chianti Classico vineyards—counting castles and old hilltop hamlets along the way. Arrive in Radda in Chianti in time for lunch after a 38 km ride, mostly on gravel.
Relax... you have only 8 km to Gaiole, following the Eroica itinerary.

• Daily distance: 46,5 km /28,5 miles
• Elevation gain: +923 m / -874 m
• Ground: 12 km asphalt and 34 km gravel
• Accommodation: Hotel Castello Spaltenna
• Meals: Breakfast

Today is dedicated to exploring all the villages and hamlets of Chianti Senese. Start from your base at "Castello di Spaltenna" in Gaiole and head to Castello di Brolio, a journey of about 10 km. Here, a coffee at the agribar in front of the winery is essential; it’s a popular meeting spot for cyclists, locals, and visitors alike. Afterward, you can venture onto the short gravel section of L'Eroica, then continue on very scenic, secondary roads until you reach Castelnuovo Berardenga. This town is worth a visit, and if you arrive around lunchtime, there are many dining options.

Back in the saddle, you will encounter other small boroughs: San Gusmé and Villa a Sesta. After returning to Brolio, you have two options to return to Gaiole: one route is downhill and relatively flat, making it somewhat easy, while the other is a challenging uphill to Castagnoli, followed by a downhill to Castello di Meleto.

• Daily distance: 55 km / 34 miles
• Elevation gain: +1013 m / -1012 m
• Ground: 44 km asphalt and 10 km gravel
• Accommodation: Hotel Castello Spaltenna
• Meals: Breakfast

If you still have energy and feel your legs stronger you can have a short ride to Badia a Coltibuono, a loop of 20 km. Back to Gaiole where you will leave bikes.

For departure you can take a bus or we can arrange a transfer (additional costs apply) to Siena for connections by rail to other parts of the region.

• Daily distance: 21 km / 13 miles
• Elevation gain: +395 m / -420 m
• Ground: All paved road
• Meals: Breakfast