The medieval Palazzo degli Anziani was originally a tower that can be seen on the south on via Consoli del Mare. It was adapted and rebuilt by Giorgio Vasari at the command of Duke Cosimo I de’ Medici who had decided to found the seafaring military order of Knights of St. Stephen in 1558 and provide them with headquarters. The name Palazzo della Carovana derives from the training (‘carovana’) the knights had to submit to. Vasari visited Pisa only in 1561 to study the square and the position of the buildings, but before two years were over, the palazzo was ready and the knights were living in it (1562-1564).

Vasari designed a symmetrical building, achieving an effect of evenness and harmony by use of pictorial decoration and stonework that gave rhythm to the facade and masked the differences among the old buildings. Tommaso Battista del Verrocchio and Alessandro Forzori from Arezzo carried out the graffitto decoration on the facade (today vastly restored) based on sketches by Vasari. At the centre is the Medici-Stephanian coat of arms, set between allegorical figures of Religion and Justice, the work of Stoldo Lorenzi (1563). The coats of arms on the corners are by Giovanni Fancelli (1564).

The double marble staircase that replaced an earlier one was built by Giuseppe Marchelli in 1821.
On the upper part of the façade, inserted in niches, are half-busts of the Medici Dukes: Cosimo I, Francis I e Ferdinand I were carved between 1590 and 1596 by Ridolfo Sirigatti; Cosimo II was carved in about 1633 by the sculptor Pietro Tacca while Ferdinand II and Cosimo III were carved in 1681 and 1718, by Giovan Battista Foggini.

Inside the palazzo, now the headquarters of the Scuola Normale Superiore, are several rooms with 16th century decorations.