DADAlytics is a semantic toolchain recently developed by the Semantic Lab at Pratt (semlab.io) to help librarians, archivists and humanities scholars generate linked data from textual resources and descriptive records. We will discuss opportunities and challenges of adopting linked open data technologies and discuss the development of DADAlytics. The use of DADAlytics will be contextualized within a real-world scenario provided by the collection of personal diaries of Mary Berenson, part of the Bernard and Mary Berenson Papers (1880-2002) held at the Berenson Library at the Villa I Tatti in Florence.