Custom tour along the epic roads of L’Eroica The Eroica is the iconic ride on vintage bikes across the whole Chianti, 200 km of pure beauty passing through many of the most beautiful tuscan cities: Siena, Montalcino, Buonconvento, plus many medieval villages surrounded by pristine San Giovese vineyards. The itinerary is along asphalted road and the “strade bianche”, typical tuscan gravel roads. The total climb is about 3500 meters, with a total length on gravel road of 110 km. During our tour we’ll visit wineries, olive oil mills, local producers and craftsman, discovering the Tuscan way of life and pleasure for healthy foods.
The Chianti countryside
The medieval center of Siena
The gravel roads of Eroica
The val d’Orcia UNESCO heritage
|1||Benvenuti nel Chianti!||Warm up ride||D|
|2||From Gaiole to Siena||Cycling 35Km/500m||B|
|3||From Siena to Buonconvento||Cycling 40Km/550m||B|
|4||Buonconvento loop||Cycling 60Km/1180m||B|
|5||From Buonconvento to Castelnuovo||Cycling 50Km/850m||B|
|6||From Castelnuovo to Gaiole||Cycling 50Km/850m||B D|
We suggest to arrive at Florence airport, according to your needs we’ll shuttle you or we’ll meet directly at our first hotel in Siena.
Conquered by the Medicis in 1585, Siena became a backwater, frozen in time, making it one of Europe’s finest examples of a preserved Gothic city. The high concentration of buildings from the 12th-14th centuries makes Siena unique, and the main square, “Il Campo,” is considered by many to be Italy’s most beautiful piazza. The famous bareback “Palio” horse race is held in the square twice a year. Our local guide will explain the mayhem and passion of the race, then take us to visit the cathedral and its medieval treasures.
Cycling: 10-20 km, depending on arrival time.
We’ll help you out in assembling your bikes, then we’ll be ready for our warm up ride along the peaceful countryside, a perfect start for the upcoming adventure.
Walking: 2 hours, hilly, urban hike.
While we’ll go for a ride, the Walkers will take a leisurely stroll through gorgeous Siena, one of Italy’s most enchanting cities.
Then we’ll set an aperitif to properly introduce the whole tour all together.Overnight: Gaiole in Chianti
We start with a blast, soon after leaving Gaiole, we’ll conquer the Brolio Castle climbing among cypress trees, This stunning real estate is probably the most important symbol of the Chianti area. It belongs to the Ricasoli family, whom Bettino di Ricasoli was the creator of the Chianti wine back in the 1872. We’ll pedal coasting the fortified walls of the Castle, then we’ll immerse ourselves in the vineyards on the valley. The views become more and more fascinating when we approach Siena, majestic medieval town where we’ll stop for a visit. The old medieval center with the Duomo and its medieval buildings tells about a rich heritage, then the arrival Piazza del Campo square, made famous thanks to the Palio joust, it’s a breathtaking experience itself.Overnight: Siena
Today it’s a quite easy stage, so you can leave Siena late on the day.
The scenery it’s absolutely peaceful, with many small ancient villages, solitary farmsteads and countryside chapels. We’ll start with a rolling stretch of gravel road among the fields, riding for some km along the Via Francigena, the ancient pilgrimage route connecting Canterbury to Rome. Almost at the end of our ride we’ll arrive to the village of Murlo, with a quite strong agricultural heritage and inhabited since Etruscan times. Our final stage is the capital of Val D’Arbia region, on the neat village of Buonconvento, surrounded by fortified walls dating back to XIV century.Overnight: Buonconvento
Today’s ride is the longest of the whole week, but we’ll pass through the vineyards of Montalcino, a perfect spot to chill with a glass of its well known Brunello. We are riding on the val d’Orcia, a quintessential tuscan landscape, made out of rolling hills dotted with cypress trees, site of the UNESCO heritage.
The scenery changes from dry and brown in fall and winter, to emerald green and blossoming in spring, to the amazing golden fields in summer. The longest climb of the whole week we’ll take us right in Montalcino, natural balcony over the countryside. After the mandatory aperitif, we’ll keep riding, stopping for lunch in Lucignano d’Asso. From here the road it’s quite relaxing taking us back to our hotel.Overnight: Buonconvento
Today we’ll start with a relaxing pace following the valley of Ombrone river, immersed in the rough and terse scenery of Crete Senesi, dotted with classy termal baths like the ones of Rapolano. Our first goal is the village of Asciano, right at the heart of the Crete area. From here we’ll climb the steep Monte Sante Marie, on of the most famous climbs on gravel of the Eroica. When on the ridge of the hill you’ll forget the challenge, thanks to the views over this unique place of Italy. Our arrival is at the luxury retreat of Villa Curina, perfectly set on a top of a hill overlooking the valley.Overnight: Castelnuovo Berardenga
Our final stage we’ll bring us back to Chianti Senese, again along tranquil countryside roads among vineyards, stopping along the way to taste some local products directly at the farm. We’ll stop for lunch in Vagliagli, a village with a perfect view and very popular among locals, great stop to have a local dish. Then we’ll pass through Radda, part of the original “Lega del Chianti” with Gaiole and Castellina. The Lega, was a military organization created by Florence in 1384 to protect the whole area. From the original Lega del Chianti was born the Chianti wine protected area, still using the black rooster as a symbol. Few more km and we’ll be back at the starting point of our week in Gaiole.Overnight: Gaiole in Chianti
Well, it’s time to say goodbye, but we are sure this part of Italy will touch your hearts and you’ll come again to visit more!Overnight: Gaiole in Chianti
You can bring your own bike or rent one from us, we offer great bikes from selected Italian and international brands: road bikes, leisure cycling, mountain bikes, e-bikes, all in perfect working conditions. We'll find the best solution for you during the tour customization.
These itineraries are original tours created for real guests, so you may want something different specifically designed to suit your own wishes.
The price of every tour is available upon requests, and varies by time of year, number of guests and level of guiding.
Start dreaming looking through it, then contact us and let's talk. We'll listen to your needs, we'll suggest ideas and propose experiences, and together we'll create your perfect voyage.
Check our GUIDED or SELF-GUIDED sections with active and cycle tours in our Mediterranean destinations.