Although drone thermography is increasingly applied as an archaeological remote sensing tool in the last few years, the technique and methods are still relatively under investigated. No doubt there are successes in positive identification of buried archaeology, and the prospection technique has clear complementary value. Nevertheless, there are also instances where thermograms did not reveal present shallow buried architectural features which had been clearly identified by, for example, ground-penetrating radar. The other way around, there are cases where the technique was able to pick up a signals of buried archaeology at a time of day that is supposed to be very unfavorable for thermographic recording. The main issue here is that the exact factors determining the potential for tracing thermal signatures of anthropomorphic interventions in the soil are many, and their effect, context, and interaction under investigated. This paper deals with a systematic application of drone thermography on two archaeological sites in different soils and climates, one in The Netherlands, and one in Italy, to investigate important variables that can make the prospection technique effective.