Enter the city through the New Bisagra Gate, the most emblematic entrance to the town. Despite its Arabic origin, it was rebuilt in Renaissance style in 1550. The construction consists of two sides: The outer side features an arch bearing the city's coat of arms which is surrounded by two circular towers, whereas the one facing the city opens up with a semicircular arch flanked by two square towers and decorated with the coat of arms of Charles I.

Next, visit the former Mosque of Cristo de la Luz. It was one of the ten in the city during the Moorish period but later was converted into a church by the Christians. The small temple is in a good state of preservation.

Walk up to the Alcazar Fortress, a stone fortification located in the highest part of Toledo, Spain. The imposing Roman quadrangular building dominates Toledo’s skyline. It was the historic witness of the Spanish Civil War as it was held against Spanish Republican forces in the Siege of the Alcazar.

Stop by the Toledo Cathedral. The landmark holds high historical and artistic value since it was situated over the foundations of a Mosque that used to be a Visigoth Cathedral. In terms of architecture, it was a melting pot of styles, including Visigothic, Mudéjar, and Renaissance. It houses fine works of art from Spain’s greatest artists, including Velázquez, Goya, and El Greco (Toledo’s most famous painter).

Step across the Hall Square to the 16th-century Toledo City Hall. Its outstanding feature is a Spanish Baroque, Herrerian-style facade. From here, you can take advantage of excellent photo opportunities of the opposite church.

Walk through the atmospheric Jewish Quarter, home to enchanting historic buildings, including synagogues and museums, along winding cobbled alleyways. This haven for the Jewish community in the 12th and 13th centuries offers a glimpse into the city’s rich past.

Next, visit the 15th-century Monastery of San Juan de los Reyes. The stunning Gothic architecture and the silence and tranquility make this place feel like heaven. The façade features the chains of captive Christians freed from the Moors, which makes the temple an iconic symbol of the city’s turbulent history.

For the rest of the tour, stroll along the medieval San Martin's Bridge on the west side of Toledo. The five-arch bridge with two defensive towers was one of the most significant in the world back in its time. From there, the views of the Tagus River and the city in the distance are breathtaking. This official National Monument stands as a testament to medieval engineering and architecture.