12 Best Sights in Castile–Leon and Castile–La Mancha, Spain

Segovia's Roman aqueduct is one of the greatest surviving examples of Roman engineering and the city's main sight. Stretching from the walls of the old town to the lower slopes of the Sierra de Guadarrama, it's about 2,952 feet long and rises in two tiers to a height of 115 feet. The raised section of stonework in the center originally carried an inscription, of which only the holes for the bronze letters remain. Neither mortar nor clamps hold the massive granite blocks together, but miraculously, the aqueduct has stood since the end of the 1st century AD.  Climbing onto the aqueduct for photos or otherwise is strictly prohibited.

As if Cuenca's famous Casas Colgadas, suspended impossibly over the cliffs below, were not eye-popping enough, they also house one of Spain's finest museums, the Museo de Arte Abstracto Español (Museum of Spanish Abstract Art)—not to be confused with the adjacent Museo Municipal de Arte Moderno (Municipal Museum of Modern Art). Projecting over the town's eastern precipice, these houses originally formed a 15th-century palace, which later served as a town hall before falling into disrepair in the 19th century. In 1927 the cantilevered balconies were rebuilt, and in 1966 the painter Fernando Zóbel created the world's first museum devoted exclusively to abstract art. The works he gathered—by such renowned names as Carlos Saura, Eduardo Chillida, Lucio Muñoz, and Antoni Tàpies—are primarily by exiled Spanish artists who grew up under Franco's regime. The museum has free smartphone audio guides that can be downloaded from the website.

This 11th-century hermitage is in ruins, but its location—on a peninsula jutting out into a bend 100 meters above the Duratón River—is extraordinary. You'll need a car to get there, about 15 minutes' drive west of Sepúlveda. After parking, walk along the marked path—the surrounding area is a natural park and a protected nesting ground for rare vultures. Try to go at sunset; when the sun sets the monastery and river glow. Inside the monastery, there's a small chapel and plaque describing the life of San Frutos, the patron saint of Segovia. An ancient pilgrimage route stretches 77 km (48 miles) from the monastery to Segovia's cathedral, and pilgrims still walk it each year. As an add-on to the trip, you can rent kayaks from NaturalTur to paddle the river ( www.naturaltur.com;  92/152–1727).

One of northern Spain's most impressive archaeological sites, this mountainous area of former Roman gold mines—located 24 km (15 miles) south of town—is a UNESCO World Heritage Site. The landscape is the result of an ancient mining technique in which myriad water tunnels were burrowed into a mountain, causing it to collapse. Miners would then sift through the rubble for gold. What's left at Las Médulas are half-collapsed mountains of golden clay with exposed tunnels peeking through lush green forest. Take in the best panorama from the Orellán viewpoint. There are hiking paths, a small archaeology exhibit, and a visitor center; the latter organizes 3-km (2-mile) walking tours—check schedules online, and call or email ahead to book ( [email protected]). A parking lot was added in 2021; the price is €3 per vehicle.

This hidden-gem museum uses the archaeological record to show what life was like in Astorga during Roman times, when the city was called Asturica Augusta. The most memorable part of the experience is the Ruta Romana, a walking tour of Roman archaeological remains (combined tickets can be bought at the museum). Descriptions are in Spanish only.

The plain facade of this 15th-century Carthusian monastery, some 3 km (2 miles) outside the historic center, belies a richly decorated interior. There's an altarpiece by Gil de Siloe that is said to be gilded with the first gold plundered in the Americas.

This house, whose facade is covered in scallop shell carvings, was built around 1500 for Dr. Rodrigo Maldonado de Talavera, a chancellor of the Order of St. James, whose symbol is the shell. Among the playful plateresque details are the lions over the main entrance, engaged in a fearful tug-of-war with the Talavera crest. The interior has been converted into a public library. Duck into the charming courtyard, which has an intricately carved upper balustrade that imitates basketwork.

This enchanting castle overlooking wild hilly countryside from above Sigüenza is now a parador; non-guests can visit the dining room and common areas. The structure was founded by the Romans and rebuilt at various later periods. Most of the current building was erected in the 14th century, when it became a residence for the queen of Castile, Doña Blanca de Borbón, who was banished here by her husband, Pedro the Cruel. During the Spanish Civil War the castle was the scene of fierce battles, and much of the structure was destroyed. The lobby has an exhibit on the subsequent restoration with photographs of the bomb damage. If you have a half-hour to spare, there's a lovely walking path around the hilltop castle with a 360-degree view of the city and countryside below.

Founded in 1131, this is Toledo's oldest and largest convent—and it's still in use. The handful of nuns who live here produce sweet wine and marzipan. The impressive complex, a bit outside the city center, includes ruins of a mosque on which a chapel was built in the Middle Ages, those of an Islamic house and courtyard (with an ancient well and Arab baths), and those of a Jewish house from the same period. Tours, offered twice daily (though not dependably—be forewarned), might include a visit to the kitchen where the Mother Superior will let you sample some sweets if she's in a good mood. Skip the touristy marzipan shops and buy the real stuff here (sweets are sold at the entrance around the corner in Plaza Padilla). There's also an adjacent cultural center with rotating history exhibits.

This contemporary art museum, constructed using minimalist wood beams and glass panels inside a 15th-century mansion, pays homage to Zanetti, a 20th-century Castilian artist known for his thought-provoking murals portraying agrarian life. Some may remind you of works by El Greco for their shimmering luminosity. It's worth the stop, and you can view the exhibit in under an hour.

Built in the 12th century and a model example of the Segovian Romanesque style, this church, a five-minute walk outside the town walls, is an architectural marvel. The exterior is notable for its arcaded porch, where church meetings were once held. The virtually untouched interior is dominated by massive columns, whose capitals carry such carved scenes as the Flight into Egypt and the Adoration of the Magi. The vaulting on the crossing shows the Moorish influence on Spanish medieval architecture. It opens for Mass only.

Most of the region's pottery is made in Talavera de la Reina, 76 km (47 miles) west of Toledo. At this museum you can watch artisans throw local clay, then trace the development of Talavera's world-famous ceramics, chronicled through some 1,500 tiles, bowls, vases, and plates back to the 14th century.