This essay is a testimony to the globally unique historical Kraków-Lublin-Vilnius route born in the “heart” of the Old Continent in the late fourteenth century. This royal route played an irreplaceable role in the integration of the Kingdom of Poland and the Grand Duchy of Lithuania completed by the creation of the Commonwealth of Two Nations. Until the early seventeenth century, this road, connecting two capital cities, was also a European cultural route enabling a lively exchange between the Western (Latin) and Eastern (Byzantine) civilizations. First, the author briefly outlines the history of the Jagiellonian route and then presents the contemporary institutionalized initiative to revive the route as an international cultural tourist trail. As a leader of this project he describes the challenges to inscribe “Via Jagellonica” Route on the World Heritage List in the category of a heritage trail. Considering the disparities between its undoubted “outstanding universal value” and the burdens arising on account of the methodology adopted by this institution, he recommends following the so-called faster path of inscribing the Lublin Union Route on the World Heritage List.