We are constantly interacting with our surrounding environment, either to find our way through the city, to find something we are looking for or just out of curiosity, trying to learn what is around us. Location based services provide us with information and many types of services based on our location. These services, when delivered in an optimal way, i.e., relevance and right amount of information, can be very beneficial for our tasks. In our work, we are focusing on retrieving the right moment to deliver the information/service based on user and environment characteristics as well as on the optimal interaction with the device and environment. For instance, we are focusing on novel interaction dialogues (mostly gaze-based and AR-based) between the user and the surrounding environment. Furthermore, we are aiming at optimizing the amount of information to be delivered based on several user characteristics, such as familiarity with the environment.