A method may include analyzing, using at least one processor, a corpus of data to identify a plurality of travel-related user inputs from a user; learning, using the at least one processor, a plurality of travel-related preferences for the user based on the plurality of travel-related user inputs; determining, using the at least one processor, a duration and location for a trip based in part on a query received from the user; accessing a plurality of points of interests (POIs) associated with the location, wherein respective point of interests are associated with a plurality of respective characteristics; based on the plurality of characteristics and the plurality of travel-related preferences, identifying a subset of the plurality of POIs to include in a trip itinerary; and presenting the trip itinerary to the user.