Unconventional geothermal resource development can contribute to increase power generation from renewable energy sources in countries without conventional hydrothermal reservoirs, which are usually associated with magmatic activity and extensional faulting, as well as to expand the generation in those regions where conventional resources are already used. Three recent drilling experiences focused on the characterization of unconventional resources are described and compared: the Campi Flegrei Deep Drilling Project (CFDDP) in Italy, the United Downs Deep Geothermal Power (UDDGP) project in the United Kingdom, and the DEEP Earth Energy Production in Canada. The main aspects of each project are described (geology, drilling, data collection, communication strategies) and compared to discuss challenges encountered at the tree sites considered, including a scientific drilling project (CFDDP) and two industrial ones (UDDGP and DEEP). The first project, at the first stage of pilot hole, although not reaching deep supercritical targets, showed extremely high, very rare thermal gradients even at shallow depths. Although each project has its own history, as well as social and economic context, the lessons learned at each drilling site can be used to further facilitate geothermal energy development.