Vehicle classification is a hot computer vision topic, with studies ranging from ground-view up to top-view imagery. In remote sensing, the usage of top-view images allows for understanding city patterns, vehicle concentration, traffic management, and others. However, there are some difficulties when aiming for pixel-wise classification: (a) most vehicle classification studies use object detection methods, and most publicly available datasets are designed for this task, (b) creating instance segmentation datasets is laborious, and (c) traditional instance segmentation methods underperform on this task since the objects are small. Thus, the present research objectives are: (1) propose a novel semi-supervised iterative learning approach using GIS software, (2) propose a box-free instance segmentation approach, and (3) provide a city-scale vehicle dataset. The iterative learning procedure considered: (1) label a small number of vehicles, (2) train on those samples, (3) use the model to classify the entire image, (4) convert the image prediction into a polygon shapefile, (5) correct some areas with errors and include them in the training data, and (6) repeat until results are satisfactory. To separate instances, we considered vehicle interior and vehicle borders, and the DL model was the U-net with the Efficient-net-B7 backbone. When removing the borders, the vehicle interior becomes isolated, allowing for unique object identification. To recover the deleted 1-pixel borders, we proposed a simple method to expand each prediction. The results show better pixel-wise metrics when compared to the Mask-RCNN (82% against 67% in IoU). On per-object analysis, the overall accuracy, precision, and recall were greater than 90%. This pipeline applies to any remote sensing target, being very efficient for segmentation and generating datasets.