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10 Top-Rated Day Trips from Siena

Siena sits in the midst of Tuscany's hill country, within easy reach of a number of charming towns, many with walls that survive from as far back as Tuscan times. It was a favorite region for abbeys and monasteries, some still active, some closed with only their churches surviving, and one, the Abbey of San Galgano, standing roofless in romantic ruin. Throughout this region are Romanesque churches with splendid medieval stone carving and a few notable art works, but the main reason tourists love to explore here is to discover the hill towns. Set overlooking beautiful undulating landscapes, these medieval villages are its main attractions.

1 Monte Oliveto Maggiore

Monte Oliveto Maggiore
Monte Oliveto Maggiore
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One of the most renowned monasteries of the Olivetans, an independent branch of the Benedictines, the large monastery of Monte Oliveto Maggiore was founded in 1313 by Bernardo Tolomei. The abbey soon developed into a flourishing monastery, was several times enlarged, and became a center of spiritual and cultural life. Even today, it is the home of an active monastic community.

You will enter through a fortress-like gate tower, begun in 1393, with terracotta reliefs by the school of Luca della Robbia. The abbey's brick buildings were erected in stages between 1387 and 1514, with some later restoration. The imposing early 15th-century church is known for its remarkably beautiful choir-stalls, 125 individual works of art created in intricate wood inlay by Giovanni da Verona from 1503 to 1505. In the cloister are outstanding frescoes showing 35 scenes from the life of St. Benedict, founder of the Benedictine Order. Nine are by Luca Signorelli, done from 1479 onwards, and the rest were done after 1505 by Sodoma. You can also tour the library, the pharmacy, and the chapter-house with a monk as a guide.

Location: Monte Oliveto Maggiore, Asciano Siena

2 Abbazía di Sant'Ántimo

Abbazía di Sant'Ántimo
Abbazía di Sant'Ántimo
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The Benedictine Abbey of Sant'Ántimo, about 40 kilometers south of Siena, may have been founded by Charlemagne and first appears in the records in 813. It grew enormously wealthy until the 14th century, when it began to decline, and was dissolved in 1462. Only the church built in the 12th and 13th centuries survives today, and it still shows its uncluttered Romanesque architecture. Unusual for an Italian church of its age, the long nave has aisles but no crossing transept and an ambulatory with chapels radiating from it, more like French churches of that period. As it was founded by monks from France, this is not surprising. A highly decorated doorway enlivens the otherwise plain facade. The capitals in the nave are carved with Romanesque plant and animal motifs alternating with interlace patterns. Look for Daniel in the lions' den on the second column on the right. Beneath is a three-aisled crypt probably dating from the 11th century. In 1992, a community of Norbertine Canons Regular settled here, so this remarkable example of monastic building once again rings with the Gregorian chants of robed monks.

Address: Castelnuovo dell'Abate

Official site: http://www.antimo.it

3 Abbazia di San Galgano

Abbazia di San Galgano
Abbazia di San Galgano
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San Galgano, founded in 1218 in the hilly country at the foot of Montesiepi, is the only Cistercian monastery built in Tuscany. It became wealthy and influential, but began a decline in the 16th century, which led to its abandonment and eventual decay. The roof of the church fell in towards the end of the 18th century, and what you will explore is among Italy's most romantic ruins. The church is a classic example of the austere Cistercian style that originated in France but never became popular in Italy. Built partly in travertine and partly in brick, even in its ruined state, the church is still impressive. Along with the church, the chapter-house, refectory, and part of the cloister survive. On nearby Monte Siepi is the round Church of San Galgano sul Monte Siepi, where you can see frescoes by Ambrogio Lorenzetti.

Address: Località San Galgano 167, Chiusdino Siena

4 Fortezza di Montalcino

Fortezza di Montalcino
Fortezza di Montalcino
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The little town of Montalcino is almost too perfect to be real, clustered tidily inside its battlemented walls on a hilltop above the rivers Ombrone and Asso. There was a settlement here in Etruscan and Roman times, but the current walls surrounding the village were built by the Sienese in 1361. The fortress is beautifully preserved, and you can tour some of the rooms inside. Walk around Montalcino's well-preserved medieval walls, with their six gates and remaining towers. The views of the Tuscan countryside from the castle are outstanding. Inside the walls is the 14th-century Church of Sant'Agostino, a plain Romanesque building with a Gothic doorway and 15th-century frescoes in the choir.

Address: Piazzale della Fortezza, Montalcino

5 Monte Amiata

Monte Amiata
Monte Amiata
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Tuscany's highest peak rises out of lower hills between the valleys of the Orcia, Fiora, and Paglia in the south of Tuscany. Known to the Romans as Mons Tuniae, Monte Amiata is an extinct volcano, whose many springs supply water to Siena and Grosseto. The mountain's workable minerals, mercury, and antimony, were exploited in Etruscan and Roman times. On the upper slopes, forests of chestnut, oak, and beech are networked with walking paths. More recently, an extensive winter sports area has sprung up, and roads are kept open in winter. A 13-kilometer road encircles the summit, and although some sections are quite steep, it's a beautiful drive.

6 Abbadia San Salvatore

Abbadia San Salvatore
Abbadia San Salvatore
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On the eastern slopes of Monte Amiata, the Abbey of San Salvatore is one of Tuscany's oldest religious houses, and in its heyday was one of the wealthiest and most celebrated in Italy. Founded in 743 by a Lombard chieftain, it was home successively to Benedictine, Camaldolese, and Cistercian orders, but today all that survives is the 11th-century church. Most impressive is the crypt, which took its present form in 1036 but was probably the original pre-Romanesque church. The groined vaulting rises on columns of various shapes and styles, many of them with exceptional carved stone capitals. The town itself, which takes its name from the abbey, still has its distinctly medieval character, with a borgo -- a walled village -- that once belonged to the Médici family.

Address: Abbadia San Salvatore

7 Pienza

Pienza
Pienza
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Near the border of Umbria, about 55 kilometers southeast of Siena, Pienza owes its orderly town layout to architect Bernardo Rossellino, and his patron Enea Silvio Piccolómini, who became Pope Pius II in 1458. Pienza was Piccolómini's birthplace, and he envisioned it as a model town laid out on clear planning principles. Work began in 1459 and advanced so quickly that three years later, Pius II was able to elevate his birthplace into a town and episcopal see named Pienza (after his Papal name). After Pius's death, however, development came to an abrupt halt.

Pienza centers on the trapezoidal Piazza Pio II, bounded by the Cathedral of Santa Maria Assunta and the Palazzo Piccolómini, one of Rossellino's finest works. He was also architect of the cathedral and designed the font in the crypt. Be sure to see the Gothic choir-stalls created in 1462 and the 15th-century painting of the Assumption by Vecchietta in the chapel to the left of the choir.

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8 Chiesa dell'Osservanza

Chiesa dell'Osservanza
Chiesa dell'Osservanza Il Tesoro di Siena
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In beautiful rolling country, not far outside Siena, the Chiesa dell'Osservanza was built in 1476 by architect Giácomo Cozzarelli. After severe damage in 1944 air raids, it was rebuilt in its original form. The aisleless nave has eight side chapels, and in the third chapel on the right is the 15th-century Reliquary of San Bernardino by Francesco d'Antonio. In the fourth, a beautiful 15th-century triptych, Madonna with SS Ambrose and Jerome, is by an artist known only as the Maestro dell'Osservanza. On the pillars of the triumphal arch (between the nave and the choir) is an Annunciation in painted terracotta by Andrea della Robbia. The sacristy has a 15th-century Pietà by Giácomo Cozzarelli. Nearby, the Museo Aurelio Castelli contains sculpture, pictures, prints, and illuminated manuscripts.

Address: Via dell'Osservanza 7, Siena

9 Colle di Val d'Elsa

Colle di Val d'Elsa
Colle di Val d'Elsa
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In almost the exact center of Tuscany, Colle di Val d'Elsa has two parts: a modern lower town in the plain and the old upper town or Colle Alto. The upper town of atmospheric old streets still has some of its 13th-century walls. The cathedral at its center, built in 1619, has a 16th-century Crucifix attributed to the sculptor Giambologna. Adjoining the cathedral, the 13th-century Palazzo Pretorio houses the Museo Archeológico, with artifacts from a nearby Etruscan cemetery.

10 Monteriggioni

Monteriggioni
Monteriggioni
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The little town of Monteriggioni can be seen from some distance, clustered inside its ring of walls that crown a hilltop above the Elsa Valley. The circuit of 13th-century walls is complete and perfectly preserved, with 14 square towers. It is so perfect, in fact, and the town so tidily arranged, that it almost seems as though it had been built as a film set.

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