The Bridge of Sighs (Ponte dei Sospiri). The enclosed bridge is made of white limestone and has windows with stone bars. It passes over the Rio di Palazzo and connects the New Prison (Prigioni Nuove) to the interrogation rooms in the Doge's Palace. It was designed by Antonio Contino (whose uncle Antonio da Ponte had designed the Rialto Bridge) and was built in 1600.

The view from the Bridge of Sighs was the last view of Venice that convicts saw before their imprisonment. The bridge name, given by Lord Byron as a translation from the Italian "Ponte dei sospiri" in the 19th century, comes from the suggestion that prisoners would sigh at their final view of beautiful Venice through the window before being taken down to their cells. In reality, the days of inquisitions and summary executions were over by the time the bridge was built and the cells under the palace roof were occupied mostly by small-time criminals. In addition, little could be seen from inside the Bridge due to the stone grills covering the windows.

A local legend says that lovers will be granted eternal love and bliss if they kiss on a gondola at sunset under the Bridge of Sighs as the bells of St Mark's Campanile toll.