Puerta de Bisagra

Toledo still bears the lasting marks of its defensive past. A city so fiercely coveted had no choice but to defend itself—and the medieval walls still standing today are proof of that, especially with gates as monumental as this one. The most famous of all is, without a doubt, the one right in front of you: the Puerta Nueva de Bisagra. It’s called the “new” Bisagra Gate because there’s also an older one nearby, known as the Puerta de Alfonso VI. That gate dates back to the 9th century and served as the main entrance to the city during Muslim rule. And while this “new” gate may look impressively well-preserved after its 16th-century reconstruction, its Muslim foundations are actually older than those of the so-called “old” gate! Take a closer look: the structure is made up of two distinct arches, separated by a small courtyard where you’ll spot a statue of Emperor Charles I of Spain—better known as Charles V, Holy Roman Emperor. The gate was rebuilt in his honor, even though Toledo was the last city to surrender during the Revolt of the Comuneros, a major uprising against his reign. At the time, many Castilian cities resisted this foreign emperor who didn’t even speak their language and was channeling their tax revenues abroad. And yet, here he is, proudly commemorated on the gate. As you pass through the inner side, look up—you’ll see the massive coat of arms of the Kingdom of Castile and León, flanked by a double-headed eagle, the emblem of the Spanish Habsburgs, the Austrian dynasty to which Charles V belonged.