Background and Objectives: Gestational hypertension has been associated with several pregnancy short-term and long-term complications, affecting both the mother and her infant’s health. The present study aims to assess the potential association of gestational hypertension with sociodemographic and anthropometry factors, perinatal outcomes, breastfeeding habits, and Mediterranean diet (MD) compliance. Materials and Methods: This is a cross-sectional study conducted on 5271 mothers that was carried out after delivery. The anthropometry characteristics and perinatal outcomes were retrieved from the mothers’ medical records. Sociodemographic characteristics, MD adherence, and breastfeeding habits were assessed via one-to-one interviews of the assigned women with qualified staff. Results: Maternal older age, being employed, family history of gestational hypertension, overweight/obesity before gestation, and abnormal gestational weight gain (GWG) independently increased the risk of developing gestational hypertension. Moreover, gestational hypertension was independently related with a greater incidence of abnormal childbirth body weight and preterm birth, not exclusively breastfeeding, and lower levels of MD adherence. Conclusions: This study highlights the importance of informing future mothers about the risk factors of gestational hypertension, underlining also that a healthy lifestyle, which simultaneously includes a healthy nutritional pattern such as MD, may decrease the risk of developing gestational hypertension and the subsequent pregnancy complications.