A computer-implemented method for generating a content based, custom labeled map, the method comprising: receiving a request for a map, including a geographic area to be displayed in the map and a type of content item to be displayed in the map; determining, based on a ranking of locations in the geographical area, a plurality of orientation points for display on the map; determining, for each of the plurality of orientation points, a plurality of pieces of content to be associated with each orientation point, wherein each of the one or more pieces of content has a weighting; for each orientation point: generating from the plurality of pieces of content a composite piece of content to associate with the orientation point, the composite piece of content having a weighting that is based on the weights of the individual pieces of content; ranking each of the plurality of orientation points based at least in part on the weight of the respective composite piece of content associated with each orientation point; and generating a map to display at the locations of the plurality of orientation points the composite piece of content respectively associated with each orientation point, wherein the size of the composite piece of content displayed at each orientation point is based on the ranking of the respective orientation point; wherein when generating the map, orientation points are selected that correspond to locations in the geographic area that are at least a minimum distance away from the locations of higher ranked orientation points in the geographic area that have previously been selected for display on the map. receiving a request for a map, including a geographic area to be displayed in the map and a type of content item to be displayed in the map; determining, based on a ranking of locations in the geographical area, a plurality of orientation points for display on the map; determining, for each of the plurality of orientation points, a plurality of pieces of content to be associated with each orientation point, wherein each of the one or more pieces of content has a weighting; for each orientation point: generating from the plurality of pieces of content a composite piece of content to associate with the orientation point, the composite piece of content having a weighting that is based on the weights of the individual pieces of content; generating from the plurality of pieces of content a composite piece of content to associate with the orientation point, the composite piece of content having a weighting that is based on the weights of the individual pieces of content; ranking each of the plurality of orientation points based at least in part on the weight of the respective composite piece of content associated with each orientation point; and generating a map to display at the locations of the plurality of orientation points the composite piece of content respectively associated with each orientation point, wherein the size of the composite piece of content displayed at each orientation point is based on the ranking of the respective orientation point; wherein when generating the map, orientation points are selected that correspond to locations in the geographic area that are at least a minimum distance away from the locations of higher ranked orientation points in the geographic area that have previously been selected for display on the map.