Shakespeare’s late romances engage with the dynastic politics of Jacobean England, particularly through the theme of achieving redemption through royal children and their politically advantageous marriages. In the narrative trajectory of The Winter’s Tale, the interruption and restoration of Leontes’s and Polixenes’ relations over the arc of the dramatic plot are entangled with the international order as defined by the bilateral relations of Bohemia and Sicilia. By the play’s end, the cross-border marriage of Perdita and Florizel forges the integration of the two kingdoms.1 In this article, I suggest that The Winter’s Tale represents the anxieties and potentialities of Anglo-Spanish peace through the Spanish match. I ground this reading upon the racialized associations of Sicilia, which have hitherto not sufficiently been considered in analyses of Leontes and his family. At the time the play was written and first performed, Sicilia was a part of Habsburg Spanish territory, having been incorporated in the sovereignty of the kingdom of Aragon following Frederick III’s 1296 coronation in Palermo.2 James I’s pursuit of peace with Continental Europe was initially welcomed by a war-weary England whose economy had been devastated by prolonged naval war with Spain. The Treaty of London was signed in 1604 and ratified in 1605 through the embassy to Valladolid headed by Lord Admiral Charles Howard, the Earl of Nottingham.