A drive management system proposes a trips combination, such as a combination of two regular trips and/or a side trip from an ongoing trip. A trips database stores a plurality of trips including regular trips. A regular trips combination proposing module automatically creates a trips combination of regular trips and proposes the trips combination to a user. The real-time trips combination proposing module finds out a trip combinable with an ongoing trip based on short-term needs which are retrieved from the trips database and proposes the trips combination to a user. The system proposes the trips combination and shows an impact which will be caused by the proposed trips combination. As a result, it is possible to support a user to plan a trips combination advantageous in some aspect.