The Puerta de Bisagra Nueva (New Bisagra Gate) is the grandest of Toledo's surviving city gates, built by Alonso de Covarrubias in 1559 to replace the older Moorish gate nearby. It marks the main entrance into the historic center from the north and sets the tone for what lies beyond: the double-headed Habsburg eagle over the arch, the towers flanking the passage, and the view through to the narrow streets of the old city.
Just a few metres away stands the older Puerta de Alfonso VI — the Moorish gate through which Alfonso VI entered Toledo in 1085 after retaking the city from the Moors. It's a much simpler structure but arguably more historically charged. Standing between the two gates you're standing at a pivot point in Iberian history.
The area around the gates is the most photogenic approach to the old city. Come in the early morning before the tour buses arrive, or at dusk when the stone turns golden. The gardens of the Paseo de Recaredo run alongside the old city walls from here, giving you the clearest view of the medieval fortifications.