Background/Objectives: Chronic wounds of the lower extremities, particularly arterial and venous ulcers, represent a significant and costly challenge in medical care. To assist in differential diagnosis, we aim to evaluate various advanced deep-learning models for classifying arterial and venous ulcers and visualize their decision-making processes. Methods: A retrospective dataset of 607 images (198 arterial and 409 venous ulcers) was used to train five convolutional neural networks: ResNet50, ResNeXt50, ConvNeXt, EfficientNetB2, and EfficientNetV2. Model performance was assessed using accuracy, precision, recall, F1-score, and ROC-AUC. Grad-CAM was applied to visualize image regions contributing to classification decisions. Results: The models demonstrated high classification performance, with accuracy ranging from 72% (ConvNeXt) to 98% (ResNeXt50). Precision and recall values indicated strong discrimination between arterial and venous ulcers, with EfficientNetV2 achieving the highest precision. Conclusions: AI-assisted classification of venous and arterial ulcers offers a valuable method for enhancing diagnostic efficiency.