The enticingly modern strain of republicanism that young Prince Cosimo III de’ Medici (1642-1723) encountered during his two sojourns in the Dutch Republic (1667-1669) proved a forceful means to reimagine Tuscany’s own, administrative past and present. Through comparative analysis of the unpublished travel journal of Medici secretary Apollonio Bassetti (1631-1699) and the diary in verse by court physician Giovanni Andrea Moniglia (1624-1700), we argue that Cosimo III’s ambitious agenda abroad was influenced predominantly by his desire to implement environmental reform and portray a contrasting socio-political model at home. Cosimo’s own journeys were followed by ongoing transnational exchange, as testified by the court’s efforts to conceptualize a Medici town atlas and cultivate exotic pineapple plants on the Tuscan soil. By importing artefacts and ideas, then, Cosimo III—just prior to his succession by Gian Gastone (1671-1737), last of the Medici grand dukes—sought to consciously craft the Medici dynasty’s lasting legacy.