This paper describes a field study conducted with our system, T-Leap, a telepresence system connecting one person (the Viewer), situated indoors, with multiple destinations (the Nodes), that roam outdoors. Here, each Node is a person wearing a module that includes a 360-degree camera and a microphone-speaker. Through our study, we demonstrate that T-Leap enables the Viewer to perform various interactions with the Nodes including being helped by them, collaborating with them, and guiding them. These interactions were demonstrated through three studies completing different tasks: 1) Nodes purchasing souvenirs for the Viewer, 2) Nodes finding objects in the park, and 3) Viewer guiding Nodes to purchase things. The studies were primarily conducted with Taiwanese locals and Japanese visitors in Taipei. Throughout the studies, we found that T-Leap worked especially well for mediating communication between a Viewer with local knowledge acting as a guide and several Nodes who were being guided. To conclude the paper, we broadly discuss our findings, the lessons we learned from our field study, and present recommendations for the future development of mobile and wearable telepresence systems.