Alarcón
This fortified village on the edge of the great plains of La Mancha stands on a high spur of land encircled almost entirely by a bend of the Júcar River....
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Alcalá de Henares
A Roman town (Complutum) in the 1st century AD, and an Arab one (al-Qala ibn Salam, hence its current name) in the 8th century, Alcalá was the site of the first meeting between Christopher Columbus...
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Almagro
The center of this noble town contains the only preserved medieval theater in Europe, which stands beside the ancient Plaza Mayor, where 85 Roman columns form two facing colonnades supporting green-frame...
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Aranjuez
Founded where the Tagus and Jarama rivers meet, Aranjuez was for centuries the spring quarters of the Hapsburg and Bourbon kings. Felipe V, the first of the Bourbon line, decided to transform the impressive...
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Astorga
Astorga, where the pilgrimage roads from France and Portugal merge, once had 22 hospitals to lodge and care for ailing travelers. The only one left today is next to the cathedral. The cathedral itself...
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Ávila
In the middle of a windy plateau littered with giant boulders, Ávila can look wild and sinister, especially with the Sierra de Gredos in the background. Modern development on its outskirts partially...
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Burgos
On the banks of the Arlanzón River is this small city with some of Spain's most outstanding medieval architecture. The first signs of Burgos, if you approach on the A1 from Madrid, are the spiky...
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Carrión de los Condes
Drive through this busy town, heading west, and cross the River Carrión to reach the Real Monasterio San Zoilo on the left. Begun in the 10th century, this former Benedictine monastery has magnificent...
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Cuenca
Though somewhat isolated, Cuenca makes a good overnight stop if you're traveling between Madrid and Valencia. The delightful old town is one of the strangest in Spain: it's built on a sloping, curling...
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Frómista
Take the small road south from Castrojeriz to Itero de la Vega and Boadillo del Camino to reach Frómista. Just before you arrive, the road crosses the Canal de Castilla, begun in 1753 with the dubious...
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Guadalajara
This quiet, affluent provincial capital is popular with Madrid commuters, who own many of the villas that sprawl down its slopes....
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León
The ancient capital of Castile-León sits on the banks of the Bernesga River in the high plains of Old Castile. Historians say that the name of the city, which was founded as a permanent camp for...
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Medinaceli
The preserved village of Medinaceli—literally "city in the sky"—commands exhilarating views from the top of a long, steep ridge. Dominating the skyline is a Roman triumphal arch from the 2nd...
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Pastrana
This pretty village was once the capital of a small duchy....
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Pedraza de la Sierra
Though it's grown somewhat commercialized, Pedraza is still a striking 16th-century village. Crowning a rocky outcrop and completely encircled by its walls, it's perfectly preserved, with wonderful views...
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Ponferrada
In a hilly region with fertile valleys, Ponferrada is a mining and industrial center that gets its name from an iron toll bridge built by a local bishop in the 1100s....
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Salamanca
Salamanca's radiant sandstone buildings, immense Plaza Mayor, and hilltop riverside perch make it one of the most attractive and beloved cities in Spain. Today, as it did centuries ago, the university...
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San Martín de Valdeiglesias
Just 6 km (4 mi) before San Martín, on the right side of the road, is a stone inscription in front of a hedge; this marks the site where, in 1468, Isabella the Catholic was acknowledged by the assembled...
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Segovia
Breathtaking Segovia—on a ridge in the middle of a gorgeously stark, undulating plain—is defined by its Roman and medieval monuments, its excellent cuisine, its embroideries and textiles, and...
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Sigüenza
Sigüenza has splendid architecture and one of the most beautifully preserved cathedrals in Castile....
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Soria
Prosperous as a sheep farming center during the 15th-century European wool monopoly that laid the groundwork for Spain's Golden Age, this provincial capital has been marred to some degree by modern development...
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Toledo
Long the spiritual capital of Spain, Toledo perches atop a rocky mount with steep ocher hills rising on either side, bound on three sides by the Río Tajo (Tagus River). When the Romans came in 192...
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Valladolid
Modern Valladolid, capital of Castile-León, is a sprawling industrial center in the middle of a flat stretch of Castilian terrain. The surrounding countryside has a desolate, wintry sort of beauty...
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Villafranca del Bierzo
After crossing León's grape-growing region, where the complex and full-bodied Bierzo wines are produced, you'll arrive in this medieval village, dominated by a massive and still-inhabited feudal...
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Zamora
Zamora, on a bluff above the Duero, is not conventionally beautiful, as its many attractive monuments are isolated from one another by ramshackle 19th- and 20th-century development. The town does have...
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