A system and method for scheduling at least one appointment to view at least one piece of property is disclosed that includes receiving from a buyer at least one appointment request to view at least one piece of property, retrieving from a server computer a set of geographic coordinates corresponding to each of the at least one pieces of property, and generating a tentative appointment schedule connecting the at least one pieces of property in a manner which minimizes travel time between the at least one pieces of property. A device for scheduling at least one appointment to view at least one piece of property is also disclosed that includes at least one processor, at least one display device, and at least one computer readable medium containing program instructions that, when executed by the at least one processor, generate an itinerary based on at least one appointment request.