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The monastery of San Juan de los Reyes began to be built in 1477 by order of Queen Isabel the Catholic to commemorate her victory at the battle of Toro in 1476. Its monumental presence right in the heart of the Jewish quarter as a royal symbol for the Catholic Monarchs. The Catholic Monarchs were initially the only source of refuge for the Jewish communities before the persecutions which occurred in the late 15th century, yet they were the ones who signed the Decree of expulsion of 1492, thereby putting a permanent end to a long period of cohabitation between Jews, Moslems and Christians. The convent’s austerity contrasts with the grandiosity of the church, adorned by spacious large windows, arches and Gothic pinnacles, on whose walls the chains of the Christian convicts which had hung there since 1494 when the Catholic Monarchs recovered them after the conquest of Granada. The church was built to house the dynastic pantheon of Queen Isabel the Catholic dedicated to St.John the Evangelist. Finally, the monarchs changed their mind after the conquest of Granada, and they are buried in the Royal Chapel of the cathedral of this city. The convent was practically destroyed in the war of Independence and was only partly rebuilt, with the second cloister disappearing according to historicist criteria of the 19th century, leaving no distinction between the old and the restored one, the best example of which is the gargoyles of the cloister.

The Cambrón Gate or Bab al-Yahud (Gate of the Jews) is the main entrance and exit of the Jewish quarter and of the city via the west. It is a highly modified gate of Muslem origin and its location coincides with the south-eastern limit of the former Jewish quarter of Toledo. The current version dates from 1576 and it was structured by repeating the Bisagra structure, in square form based on a small interior courtyard surrounded by four towers covered by slate chapters. The Cambrón Gate has fragments with Roman reliefs similar to those of the Sol gate. On both sides, there are Renaissance gateways with coats-of-arms, that of the city on the exterior and that of Felipe II on the interior. Under the latter a beautiful image of St.Leocadia can be seen, the patron saint of Toledo. The gate also bears the inscription reminding that the residents of Montes de Toledo, part of the city, are except from passage rights. Its name is associated with brambles, thorny plants which are abundant in the area.

The Arquillo del Judio (Small Arch of the Jew) is located near the confluence of Reyes Católicos and Ángel streets where the Sofer synagogue was situated. This small arch is was passage which joined the districts of Assuica and Alacava with the main Jewish quarter via the Travesía del Arquillo, which is said to have borne witness to the sale of the jewels of Queen Isabel the Catholic to finance Colombus´ American venture. The present arch is not the original one, but was reconstructed to look like the original.

The San Martín Bridge, located in the old Jewish quarter of El Degolladero, leads to the Puerta del Cambrón, an ideal place to start the journey to the Jewish quarter of Toldeo. The bridge is alongside the waters of the Tagus, with a view of the city, providing a better understanding of the complex, difficult but fascinating history of a Jewish quarter like that of Toledo. A Jewish quarter where the keys of the houses of those who had gone into exile in 1492 had become the greatest symbol of the Sephardi nostalgia. The Jewish quarter of Degolladero largely coincided with the current Reyes Católicos street and the San Martín bridge and river. It took this name because this was the site of the Jewish butcher´s, where the poultry and cattle were slaughtered. A statue of Isabel the Catholic (1451-1504), the Queen of Castile, was located at Reyes Católicos street, very near the monastery of San Juan de los Reyes. Under the edict of expulsion of 1492 the Catholic Monarchs sent between 170,000 and 180,000 Sephardis into exile.