Featured here are sun paintings and sun sculptures, as Oliver Wendell Holmes, the inventor of the portable stereoscope, called stereoscopic photographs back in 1859. His invention was later developed into a complete travel system with maps and a detailed guidebook. The Underwood Stereoscope Travel System is a forerunner of Google Earth, meant to entertain, educate, and ignite the user’s geographic imagination. Indeed, it exclaims the experience that it provides is that of being in the place itself rather than being in our home seeing a picture of the place. In our simulation, the stereoscopic kit turns into a time-traveling machine. We have chosen to see Italy through the stereoscope, the same way a homebound innocent abroad or a virtual traveler might have experienced it at the turn of the twentieth century. Yet at the end of our journey, we must ask ourselves, what is the experience that the stereoscope offers us today in the age of virtual reality as we look back through its dual lenses?