Backgorund: This study aimed to explore the relationship between different types of skin cancer and factors such as sun exposure and photoprotection measures in a Greek cohort on the island of Crete. Methods: This cross-sectional observational study was conducted in the Dermatology Department of the University Hospital in Heraklion, Crete, between January 2019 and January 2024. The study population included consecutive patients diagnosed with basal cell carcinoma (BCC), squamous cell carcinoma (SCC), and malignant melanoma (MM), as well as healthy controls. The participants completed a self-reported questionnaire covering demographic and clinical data as well as questions about sun exposure and photoprotection habits. Results: A total of 265 skin cancer patients and 106 healthy controls participated in the study: 50.6% of the patients had basal cell carcinoma, 35.1% had squamous cell carcinoma, and 14.3% had malignant melanoma. The cohort comprised 41.5% females and 58.5% males, with a mean age of 73.2 years. As expected, the patients with skin cancer had a lighter skin phototype compared to the healthy controls (p < 0.01). They also reported greater occupational (p < 0.01) and leisure sun exposure (p < 0.01) and a higher median number of vacation weeks spent outdoors before the age of 18 (p = 0.030). Furthermore, the healthy controls were more likely to use sunscreen (p = 0.035) and preferred higher SPF (>50) when they did so (p < 0.01). The healthy controls also reported more frequent use of sunglasses (p < 0.01), brimmed hats (p < 0.01), and long-sleeved clothing (p < 0.01) compared to the skin cancer patients. Conclusion: This is the first study to analyze sun exposure and photoprotection behaviors in patients with nonmelanoma skin cancer (NMSC) and malignant melanoma (MM) in Crete, revealing the key associations and underscoring the need for targeted prevention strategies.