Background/Objectives: Representing the most common malignancy worldwide, skin cancer requires timely detection to improve prognosis. Both educational level of the patients and health literacy are important variables in terms of prevention and diagnosis in early stages of the disease, but data from Central and Eastern Europe are limited. Methods: We realized a prospective observational study that included 76 patients who were diagnosed with skin cancer and treated at the “Prof. Dr. I. Chiricuță” Institute of Oncology in Cluj-Napoca, Romania. Demographic, clinical, histopathological, and psychosocial data were collected in a standardized form. The primary aim was the measurement of diagnostic delay, defined as the interval since symptom onset until diagnosis. Secondary variables included education level, place of residence, participation in awareness campaigns and understanding capacity. Statistical analyses were applied. Results: The mean age in the cohort was 58.3 years; 52.6% were male and 84.2% were urban residents. The most frequent histological type was melanoma (47.4%), followed by basal cell carcinoma (36.8%), and squamous cell carcinoma (10.5%). The median delay in diagnostic was equal to 3 weeks. Education level was significantly related to earlier presentation (Kruskal–Wallis, p = 0.043), with shorter delays noticed in patients with university or postgraduate degrees (compared to those with secondary education). However, there were no significant differences between patients with rural and urban provenience (p = 0.483). Patients’ capacity of understanding showed no correlation with diagnostic delay, but their prior participation in awareness campaigns was strongly associated with higher comprehension (p < 0.001). Also, skin self-examination did not significantly impact time to diagnosis (p = 0.86). Conclusions: Higher levels of education and patients’ exposure to awareness campaigns might represent predictors of shorter diagnostic delay, highlighting the impact of public health initiatives and targeted educational strategies to improve early detection of skin cancers in Romania. However, the findings must be interpreted in light of the study’s limitations, namely the relatively small sample size and single-center design.