In this paper, we explore the design and use of conversational telepresence robots to help homebound older adults interact with the external world. An initial needfinding study (N=8) using video vignettes revealed older adults' experiential needs for robot-mediated remote experiences such as exploration, reminiscence and social participation. We then designed a prototype system to support these goals and conducted a technology probe study (N=11) to garner a deeper understanding of user preferences for remote experiences. The study revealed user interactive patterns in each desired experience, highlighting the need of robot guidance, social engagements with the robot and the remote bystanders. Our work identifies a novel design space where conversational telepresence robots can be used to foster meaningful interactions in the remote physical environment. We offer design insights into the robot's proactive role in providing guidance and using dialogue to create personalized, contextualized and meaningful experiences.