Starting in 2016, the Smithsonian American Art Museum undertook a series of experiments in producing Virtual Reality (VR) applications, in order to gain hands-on experience with the technologies involved, and to increase the museum staff’s firsthand knowledge of the medium. The objective of the projects was to evaluate different types of VR—from relatively lightweight mobile apps to robust, room-scale experiences—in order to understand the strengths and weaknesses of each as a vehicle for delivering educational and aesthetic experiences to a remote audience, in keeping with an art museum’s mission. This paper presents and analyzes two primary case studies from among these experiments. The first case study is SAAM’s in-house production of “Renwick Gallery WONDER 360,” a VR app for mobile devices, created as a compliment to the 2015 WONDER exhibition at its Renwick Gallery. The second case study, “Beyond the Walls,” is a more ambitious, room-scale VR experience for the HTC Vive system, and was developed with support from our commercial partner, Intel. Each of these case studies centers around an application meant to offer a virtual visit to a section of the art museum galleries, and together they give a glimpse into the possibilities for virtual museum visitation in the future. The paper analyzes the costs, benefits, and lessons learned in each project, and suggests an approach and set of criteria for evaluating future developments in the VR space that could be utilized by museums both large and small.