This paper uses TripAdvisor as its subject matter and analyzes the photos posted there by travelers. In addition, it considers how the application evokes the imagination of the trip, as well as how ...it reconstructs the experience of travel. More specifically, with the TripAdvisor site, along with the smartphone app, we can utilize reviews and price comparisons for hotels, restaurants, and sightseeing information by city, area, and such. For this paper, we focus on the digital photo and analyze two functions related to it: "travel timeline" and "360 degree panoramic photographs". From this, we can achieve not just a "representation of a trip", but a "simulation of a trip", and we can consider expanding it even further by developing a mechanism to make "imagination of travel" possible. In this way, with this study, we aim to use the image data to create a more realistic simulation of the act of traveling, projecting an imagined form of a contemporary trip.