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Design-led wineries along the L’Eroica bike trail

Here’s a tour inspired by the famous cycling event in the province of Siena

Bike lovers will doubtless have heard about the L’Eroica, one of the most traditional and striking cycling events in Italy. Every year, on the first Sunday in October, hundreds of cyclists come to Tuscany ready to get involved in the vintage biking event. L’Eroica uses vintage bikes off the beaten track along trails in the province of Siena.

As well as being a competitive route, the trails of L’Eroica can be used all year round. The route winds its way along approximately 200 km among the old vineyards of Chianti, the striking lunar landscape of the Crete Senesi and picture postcard views of the Val d’Orcia. In short, it’s the perfect opportunity to see some of the best views in Tuscany.

Here’s a route inspired by the permanent and springtime L’Eroica routes to discover some of the most beautiful design-led wineries in Tuscany, which belong to the "Wine Architecture" circuit.

GAIOLE IN CHIANTI. Let’s begin in Gaiole, the little town in the heart of the Chianti Classico, nestled between age-old castles and Romanesque churches. Then we head in the direction of Florence, stopping at one of the masterpieces of contemporary architecture: Cantina Antinori, in Chianti Classico.

CANTINA ANTINORI IN CHIANTI CLASSICO. The building is based on a profound relationship with the land, with low environmental impact and high energy saving. Upon first glance, it resembles a big hill with two cracks cut into the vine-growing ground. Brick red in colour, like the soil, the cellar was built using natural materials, in total harmony with the surrounding area into which it blends. Visitors can discover how wine is made, from the vineyard to the bottle, through vinification and the ageing process.


CASTELLO DI FONTERUTOLI. Now we head south to visit the winery Castello di Fonterutoli, whose distinctive style is contemporary classicism in its functions, design and spaces. The winery designed by architect Agnese Mazzei appears out of nowhere, without impacting on the delicate balance between nature, the land and the centuries-old village – it makes an impression on visitors inspiring growing awe and wonder.


SIENA. Now we leave these two architectural gems behind and start our journey towards Siena, the city of the Palio and one of the loveliest places in Tuscany, high on tradition and places to see. From the impressive Torre del Mangia in Piazza del Campo to the magnificent Duomo, the museum complex of Santa Maria della Scala and the magnificent sewer system, there’s no shortage of things to see.

BUONCONVENTO. Let’s carry on south reaching Buonconvento, which is where the springtime L’Eroica cycle route begins. This small, striking town is still surrounded by medieval walls built in the 1300s.

MONTALCINO. Montalcino is our next stop, the home of Brunello, the preferred destination of millions of wine lovers from all over the world. It’s a medieval gem of a town nestled in the hills of Siena that is well worth exploring. Visit the 14th-century fortress, home to a fantastic wine bar (“enoteca”) where you can taste some really amazing wines.

CANTINA DI MONTALCINO. Just in front of the hill leading to this small town near Siena stands Cantina di Montalcino, surrounded by the meadows, olive groves and vineyards of Val di Cava. Land, nature, technology and tradition blend togeter in this only winemaking cooperative in the area, with about 100 small agricultural firms as members. The winery has been restored recently thanks to an extensive modern architectural project that’s in harmony with the surrounding hills to make environmentally respectful wines.

BAGNO VIGNONI. A short distance away, we come to Bagno Vignoni, a small medieval village with a thermal pool in the middle of the settlement, where leading figures have enjoyed the water over history such as Emperor Frederick II, Lorenzo de' Medici and Saint Catherine.

SAN QUIRICO D’ORCIA. About 10 minutes by car from here, you find San Quirico d’Orcia, a must-see for visitors to the Val d’Orcia. The town is particularly pretty with its paved streets and stone fountains. The village stood along the Via Francigena, testifying to the presence of the Ospedale della Scala, which once provided shelter to pilgrims. Also remember to visit the remains of the bridge house and the Horti Leonini, typical 16th-century gardens which are entered from between the walls and the square.

PIENZA. We continue our trip to Val d’Orcia in Pienza, the ideal Renaissance town. Acknowledged by UNESCO as a World Heritage Site, the small and beautiful town is popular due to its culinary specialities, especially pecorino toscano DOP.

MONTEPULCIANO. About 14 km separate Pienza from Montepulciano, our next stop and home to Vino Nobile wine. The scenery you spot just before arriving here is exactly the scene that we all conjure up in our mind when we think of Tuscany: long expanses of verdant hills and fields.

Take the time to walk along the street that passes through the elegant town centre to reach the central piazza. Piazza Grande, situated at the highest point in the town, is dominated by the large tower and Gothic-style facade of the town hall (Palazzo Comunale). Opposite the town hall you can admire the Cathedral dating to the late 16th century.

CANTINA SALCHETO. Not far from the town, we get to Cantina Salcheto, a model company in terms of integrated environmental management that powers itself independently, boasting world records for its carbon and Water footprints. The estate covers 65 hectares, 50 of which are organic vineyards.


SAN GIOVANNI D’ASSO. Continuing along the road north, we come to San Giovanni d’Asso, famous for its truffles from the Crete Senesi and the Val d’Orcia. Don’t miss the Mostra Mercato del Tartufo Marzuolo truffle event in March and the Mostra Mercato del Tartufo Bianco delle Crete Senesi white truffle fair in October and November. If you’re a true truffle lover, visit the Truffle Museum.
ASCIANO. Just 15 minutes away by car, we reach Asciano, in the heart of the Crete Senesi. Don’t miss the beautiful churches in the town centre, full of works of art, the Casa Corboli, the Archeological and Sacred Art Museum and the beautiful Piazza del Grano.

CASTELNUOVO BERARDENGA. Returning to the hills of Chianti, home to Castelnuovo Berardenga. An ancient settlement, Berardenga is named after Berardo di Ardengo, a noble of Frankish lineage who lived in the late tenth century. The most striking aspect of the immense medieval legacy of Castelnuovo Berardenga is the large number of castles. The one that most deserves our attention is Montalto, which has belonged to the Berardenghi since the ninth century. Our itinerary ends in Castellina in Chianti, right where we began, following the route of the L’Eroica.