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

This museum, housed in the ancestral seat of the Calatrava Order of Knights, displays models of the Roman amphitheaters in Mérida (Extremadura) and Sagunto (near Valencia), both still in use, as well as costumes, pictures, and documents relating to the history of Spanish theater. Kids love handling the antique instruments previously used for sound effects during productions.

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.

In what were once the cellars of the Bishop's Palace, this museum's collection includes a jewel-encrusted Byzantine diptych of the 13th century, a Crucifixion by the 15th-century Flemish artist Gerard David, a variety of carpets from the 16th through 18th centuries, and two small El Grecos.

Built in the mid-16th century by Rodrigo Gil de Hontañón and one of the most stunning Renaissance palaces in Spain, this lavish abode was meant for an illegitimate son of Alonso de Fonseca I. The building, which opened to the public in 2018, is flanked by towers and has an open arcaded gallery running the length of the upper level. Such galleries—often seen on the ground floor of palaces in Italy—were intended to provide privacy for the women of the house and to cool the floor below during the summer. Walking the halls on either the day- or nighttime tour, feast your eyes on seldom-before-seen Titians, Coellos, and other masterpieces presided over by the Alba family. 

The Arco de Santa María frames the city's loveliest promenade, the Espolón. Shaded with black poplars, it follows the riverbank.

León's busiest tapas bars are in and around this 12th-century square. The area is called the Barrio Húmedo, or "Wet Neighborhood," allegedly because of the deluge of wine spilled here late at night.

This square was once called Plaza del Grano (Grain Square) because it was the site of the city's corn and bread market. Also here is the church of Santa María del Camino, where pilgrims stop on their way west to Santiago de Compostela. The fountain in the middle of the plaza depicts two cherubim clutching a pillar, symbolizing León's two rivers and the capital.

Toledo's main square was built in the early 17th century as part of an unsuccessful attempt to impose a rigid geometry on the chaotic Moorish streets. Over the centuries, this tiny plaza has hosted bullfights, executions (autos-da-fé) of heretics during the Spanish Inquisition, and countless street fairs. Today it's home to the largest and oldest marzipan store in town, Santo Tomé. You can catch intracity buses here, and the tourist office is on the south side of the plaza.

This is the heart of the old town, and on Wednesday and Saturday mornings the arcaded plaza bustles with farmers selling produce and cheeses.

In front of the cathedral, this historic square comes alive every night and especially on weekends, when visiting Madrileños and locals gather at casual cafés that line the perimeter. There's a gazebo in the middle that occasionally hosts live music. (Otherwise it's occupied by children playing while their parents dine nearby.)

The south side of the cathedral overlooks this harmonious arcaded Renaissance square that hosts a medieval market on weekends.

Roman in origin, this is the city's oldest bridge. Next to it is a heavily restored castle built after the Christian capture of 1085 and, above this, a vast and severe military academy, an eyesore of Francoist architecture. From the other side of the Río Tajo, the bridge offers fine views of Toledo's historic center and the Alcázar.

This pedestrian bridge on the western edge of Toledo dates to 1203 and has splendid horseshoe arches. At 40 meters (131 feet) long, it was one of the longest bridges in the world at the time of construction.

Next to this bridge is an Iberian stone bull, and opposite the bull is a statue commemorating the young hero of the 16th-century picaresque novel The Life of Lazarillo de Tormes and of His Fortunes and Adversities, a masterpiece of Spanish literature. There's also a 300-meter track and a network of paths on the south side of the bridge ideal for jogging.

In an unlikely location—among apartment blocks a good 10-minute walk from the walls—is one of the most important religious institutions in Castile. The monastery was founded by Fernando and Isabel with the backing of Inquisitor-General Tomás de Torquemada, largely responsible for the expulsion of the Jews per the Alhambra Decree, who is buried in the sacristy. Further funds were provided by the confiscated property of converted Jews who were dispossessed during the Inquisition. Three decorated cloisters lead to the church; inside, a masterful high altar (circa 1506) by Pedro Berruguete overlooks a serene marble tomb by the Italian artist Domenico Fancelli. One of the earliest examples of the Italian Renaissance style in Spain, this work was built for Prince Juan, the only son of Fernando and Isabel, who died at 19. After Juan's burial here, his heartbroken parents found themselves unable to return. 

The university's walls, like those of the cathedral and other structures in Salamanca, often bear large ocher lettering recording the names of famous university graduates. The earliest names are said to have been written in the blood of the bulls killed to celebrate the successful completion of a doctorate (call it medieval graffiti!). The elaborate facade of the Escuelas Mayores (Upper Schools) dates to the early 16th century; see if you can spy the eroded "lucky" frog that's become the symbol of the city—legend has it that students who spot it on their first try will pass all their exams. The interior of the Escuelas Mayores, drastically restored in parts, is disappointing after the splendor of the facade and not worth entering unless you're a diehard Spanish literature buff. But if you are, the lecture hall of Fray Luis de León, where Cervantes, Pedro Calderón de la Barca, and numerous other luminaries of Spain's golden age once sat, is of interest, as is the grand library. Don't miss the serene courtyard (free entry) of the Escuelas Menores (Lower Schools) that wraps around the patio in front of the Escuelas Mayores.