Background. Drones are increasingly integrated into recreational and economic activities, including for medical uses. In this scenario, drones carrying medical equipment or patients may fly over someone else’s property. This raises the question of how conflicts between drone users and landowners arising from the medical use of drones are resolved. This question predominantly revolves around the vertical extension of property rights. Aim and methodology. This article offers a comparative study of how these conflicts are tackled in Italy and the Netherlands, exploring the different operational solutions offered by their respective legal frameworks. In particular, the aim of the article is two-fold. First, the article intends to assess to which extent the Italian and Dutch operational solutions differ or converge, based on insights from the legislative, judicial, and doctrinal legal formants. Secondly, based on this comparative analysis, the article makes use of socio-economic considerations to assess the potential impact of the reconstructed Italian and Dutch operational solutions on the advancement of drone medical uses. Conclusions. The article argues that the current legal framework fails both to facilitate the use of drones, also for medical emergencies, and to protect landowners’ rights. A clear-cut height above which drones can fly (and under which drones cannot fly) can provide more clarity over the respective spheres of interest of the parties concerned.