Only one of Europe’s micro-states is a republic: the Republic of San Marino. This non-EU Member State is an enclave of Italy and sits in a mountainous region of the Apennine Mountains. Given its proximity to the EU, being fully surrounded by it, and the extent to which integration through law has occurred within the EU, the law and policy of EU external relations demands that EU-San Marino relations must exist in some way. Yet the EU’s legal relations with third states in Europe have evolved along different trajectories, accounting for the individuality and uniqueness of each. As uncovered in this article, the EU-Sammarinese relationship stretches across a limited array of international agreements, with their own specific width and depth. Taken together, this mishmash of accords, and the way in which regulatory alignment is designed by them, portrays an outdated model of relations that need an update. With an envisaged association agreement between the EU and San Marino on the horizon, this article analyses the legal relations of the parties as they presently stand, accounting for their history, the substance of the international agreements, and the promise of what future legal relations ought to achieve between them.