Best attractions and places to see around Asciano include a rich tapestry of historical landmarks and natural landscapes. This charming medieval village is nestled in the heart of the Sienese hills, offering a unique "moonscape" of clay hills known as the Crete Senesi. Its ancient origins are evident in Etruscan and Roman remains, while its medieval character is preserved in its narrow streets and historic buildings. The region provides diverse opportunities for exploration, from cultural sites to scenic viewpoints.
Last updated: April 24, 2026
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Porta Romana is one of the ancient gates in the walls of Siena, located on the route of the ancient Via Cassia. It was built in 1327 - 1328 by Agnolo di Ventura and Agostino di Giovanni, equipped with battlements and a defensive wall. In 1417, Taddeo di Bartolo was commissioned to paint the fresco that was to adorn it with a depiction of the Virgin, like the other city gates, to implore divine protection for the city. In 1978, the frescoes, due to advanced deterioration, were detached and transferred to the Basilica of San Francesco. However, there is a Roman inscription at the Porta Romana!The inscription was written on a travertine tablet and, based on its graphic characters and content, can be dated to the Augustan period (27 BC – 0) saying "Silvanus sacr(um) / C. Victricius / Memor VIvir / [a] ugustalis posuit" = Caio Victricio Memore Seviro augustale dedicated a small temple to Silvanus.
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In Siena, as we know, your eye always falls there, on the shell-shaped Campo or the striped marble of the Duomo. And rightly so. But then there are those places that speak to you in a different voice, more raspy and sincere. Porta Romana is one of them. Let's be clear: this isn't a small archway placed there for show. This is a beast of brick and stone, a fortress planted to the south to tell those arriving from Rome: "Be careful, you're entering Siena." It's massive, imposing, it makes you feel small and immediately reminds you that this city was once a serious thing, a power that had to be defended. It has none of the frills of other monuments; it gets straight to the point, and for me, its charm begins right there.
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The Porta Romana, also known as Porta Nuova, is one of the gates in the medieval walls of Siena. The gate was built in 1327-1328. It has a complex structure with two separate portals separated by a small courtyard, and the inner gate is higher than the outer one. The large arches are covered with travertine marble. In 1417, Taddeo di Bartolo was commissioned to paint the Madonna icon on the inner portal, dedicated to the protection of the city. The painting was further updated by Sassetta and later Sano di Pietro who completed it in 1466.
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Excellent starting point for immersing yourself in the Tuscan dirt roads and in the landscapes of the collective imagination. A cyclist's paradise, provided that in the warm months it is well equipped with water resources (refueling fountains are scarce on the "Eroic" circuits).
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at the entrance of Siena, very beautiful and characteristic
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Beautiful village, less famous than others, but also worth a visit.
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A stop in Buonconvento is absolutely recommended because it is a delightful small town. Stop for half an hour, tour the small village, have a coffee in the bars frequented by many cyclists and then set off again.
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Asciano boasts a rich history. You can explore the Romanesque Basilica of Sant'Agata, the 13th-century Church of San Francesco with its impressive frescoes, and the medieval Palazzo Corboli Museum, which houses Etruscan and medieval art. Don't miss the partially preserved 14th-century Medieval Walls and the ancient Etruscan Necropolis.
The region is famous for the Crete Senesi, an extraordinary 'moonscape' of clay hills formed by erosion. This unique landscape changes colors with the seasons and is perfect for nature lovers and photographers. You can also visit the Parco delle Crete for panoramic views and numerous trails, or the Bosco della Ragnaia for a blend of art and nature.
Yes, several attractions are suitable for families. The charming walled village of Buonconvento is a delightful stop. In Siena, families can enjoy exploring the historic Palazzo Pubblico and Piazza del Campo, and the impressive Siena Cathedral. The public gardens, Giardini Pubblici di Asciano, also offer a peaceful spot for relaxation.
The rolling hills and unique landscapes around Asciano are ideal for outdoor activities. You can find numerous routes for mountain biking, cycling, and road cycling. Explore the 'Crete Senesi' on two wheels or discover scenic viewpoints. For detailed routes, check out the MTB Trails around Asciano, Cycling around Asciano, and Road Cycling Routes around Asciano guides.
Asciano offers several cultural experiences. The region is renowned for its wine production, so visiting local wine cellars for tastings is a popular activity. You can also experience local markets and festivals, such as the Asciano White Truffle Market Exhibition in autumn, or the traditional 'Palio dei Ciuchi' donkey race.
Absolutely. The Basilica of Sant'Agata is Asciano's most important church, featuring a Lombard bell-tower and 16th-century frescoes. The Church of San Francesco, built on the ruins of a Lombard castle, showcases Franciscan style architecture and 12th-century frescoes. A few kilometers away, the imposing Abbey of Monte Oliveto Maggiore, founded in the 14th century, is famous for its cloister adorned with frescoes by Luca Signorelli and Sodoma.
For a unique experience, visit Site Transitoire, a spectacular land art installation by Jean-Paul Philippe. The Bosco della Ragnaia offers a whimsical blend of art and nature with sculptures amidst ancient oaks. The historic Via Lauretana, an ancient Etruscan-Roman road, also provides a fascinating panoramic route through the landscape.
The Crete Senesi landscape changes beautifully with the seasons. Spring and autumn are generally ideal for outdoor activities like hiking and cycling, offering pleasant temperatures and stunning scenery. Autumn also brings local festivals like the White Truffle Market. Summer can be warm, but still enjoyable for sightseeing, especially in the mornings and evenings.
Yes, Asciano has several art museums. The Palazzo Corboli Museum (Civic Archaeological and Sacred Art Museum) houses Etruscan and medieval art. The Museo Cassioli is entirely dedicated to 19th-century Sienese painting, showcasing works by Amos Cassioli and his son. Additionally, the Museo d'Arte Sacra, next to the Basilica of Sant'Agata, exhibits works by Sienese school painters from the 14th and 15th centuries.
The entire Crete Senesi region offers incredible photographic opportunities, especially at sunrise and sunset, due to its unique 'moonscape' and changing colors. The Parco delle Crete provides rolling hills and panoramic views. Many visitors also enjoy dedicated sunset photography tours to capture the evocative Sienese hills.
The Piazza del Grano is a historic square in Asciano. It features a 15th-century fountain created by Antonio Ghini, which depicts allegories of medieval culture. It's a charming spot to experience the village's historical atmosphere.
Yes, the delightful village of Buonconvento is a must-see. It is surrounded by well-preserved historic walls dating back to the late 1300s and is considered one of the most peculiar 'Borghi' of Central Italy. It's a great place to stop, explore the small village, and enjoy a coffee.


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