A system and method for creating a dynamic trip plan for a driver between a first site and a second site in addition to providing parking suggestions to the driver. The system and method includes computing an estimated time of arrival and an estimated time of departure for a plurality of stops of travel of a vehicle between a first site and a second site, generating a dynamic trip plan based on the estimated time of arrival and the estimated time of departure, receiving a driver input indicating at least one of an adjusted time of departure from a stop, an adjusted time of arrival at a stop, or an adjusted break time, and updating the dynamic trip plan based on the driver input.