In 2014, as part of the Kortlagning klaustur á Íslandi (Mapping Monasticism in Iceland) archaeological project, bulk samples retrieved from various archaeological sites associated with Icelandic monasticism were subsampled for pollen analysis. The objective was to discern something about the character of the past vegetation that surrounded the sites under archaeological investigation as well as to detect the presence of exotic pollen derived from plant species with medicinal, culinary, and other utilities. Two methods were applied: a standard pollen count (up to 300 pollen grains) and rapid scanning (where all pollen were examined but only exotics were recorded). The pollen surveys showed mixed results in achieving the intended insights, mostly due to taphonomic processes (wind and depositional environments), exacerbated by poor chronological resolution. However, there was sufficient data to suggest that careful selection and analysis of subsamples from archaeological contexts can allow some reconstruction of past vegetation communities and land use practices. The presence of cereal type pollen might suggest cultivation and/or storage of grain in association with medieval archaeological contexts. Furthermore, palynology was able to discern some evidence of the importation of plants for medicinal purposes to Iceland.