Building upon the positive outcomes and evidence of dissemination across the community of the first Special Issue “Remote Sensing and Geosciences for Archaeology”, the second edition of this Special Series of Geosciences dedicated to “Earth Observation, Remote Sensing and Geoscientific Ground Investigations for Archaeological and Heritage Research” collects a varied body of original scientific research contributions showcasing the technological, methodological, and interpretational advances that have been achieved in this field of archaeological and cultural heritage sciences over the last years. The fourteen papers, published after rigorous peer review, allowed the guest editor to make considerations on the capabilities, limitations, challenges, and perspectives of Earth observation (EO), remote sensing (RS), and geoscientific ground investigations with regard to: (1) archaeological prospection with high resolution satellite SAR and optical imagery; (2) high resolution documentation of archaeological features with drones; (3) archaeological mapping with LiDAR towards automation; (4) digital fieldwork using old and modern data; (5) field and archaeometric investigations to corroborate archaeological hypotheses; (6) new frontiers in archaeological research from space in contemporary Africa; and (7) education and capacity building in EO and RS for cultural heritage.