This chapter focuses on elements of design for teachers and curriculum developers for authentic virtual fieldtrips in the humanities. This chapter considers how virtual fieldtrips (VFTs) and inquiry (i.e., fieldwork) can better incorporate the affordances of physical fieldtrips beyond engaging with a specific virtual or digital historic site or museum. Authenticity requires engagement in real-world problems using inquiry models informed by different disciplines for engaging with authentic data, perspectives, or artifacts (e.g., Shaffer, Resnick (1999) “Thick” authenticity: new media and; Stoddard, Contemporary issues in technology and teacher education 9:412–438, 2009). When using VFTs, however, many teachers focus on accessing the virtual museum or historic site as the primary “destination” for a fieldtrip. They do not necessarily consider other elements that can make the VFT authentic for students—elements that make students feel like they are not doing “school” but are transported to a different place. These aspects of a fieldtrip are also important for engaging in an authentic form of inquiry that can transfer to how young people make sense of or engage with cultural sites outside of class activities—and inform their civic understandings and engagement. These elements include pre- and post-VFT background research and discussions, establishing the context and culture of the VFT destination, engaging in authentic inquiry at the destination, examining historic sites and museums through the perspective of public history and museum studies, and strategies for engaging with the complex and sometimes difficult stories and perspectives of the virtual destination and history or cultural perspectives represented.