Starting with Pompeo Batoniߣs bravura portrait of The Honourable Colonel William Gordon, 1766 (Fyvie Castle), this chapter considers painted portraiture as a vehicle through which educated, socially privileged young Scotsmen like Colonel Gordon, the 8th Duke of Hamilton and James Boswell fashioned their identity while on the grand tour in Europe. Drawing on the published and unpublished accounts of travelling Scots, including Dr John Moore, the Duke of Hamiltonߣs tutor, grand tour portraits by artists including Pompeo Batoni and Nathaniel Dance are considered as potent means for representing, disseminating and reproducing familial and homosocial relations. In much the same way that the grand tour was seen as a means for transcending geographical barriers and cultural stereotypes, so we will see how Scots in Italy are imaged first and foremost as inclusively British, rather than exclusively Scottish, while engaged in this social and geographical rite of passage across cosmopolitan Europe.