Architecture that comprises features that enable smart searches along a route based on time to entities along the route and off the route, a user experience (UX) that showcases rich entities along the route, saving, sharing and editing capabilities across devices and users, smart ranking and filtering of entities, and user preferences and digital personal assistant interaction. After an itinerary is built, the itinerary can be saved for future use and/or shared with friends and/or other devices. Users can change the itinerary on-the-go by searching and adding entities, at a later time, for example. A digital personal audio assistant can be utilized to provide guidance based on the itinerary, and ask users if they want to take a particular exit to visit some desired location (e.g., place of interest).