Background: There is still room for further studies aimed at investigating the most widespread diets in the Mediterranean area. The objective of the study is to analyze the relation of food group intake to clinical chemical indicators of health, and also to compare the food group intake with healthy well-known diet indices. Methods: Lifestyle, dietary, and clinical data collected in 2005/2006 and 2012/2018 from Castellana Grotte, located in the rural area of Apulia, were analyzed. The study populations included newly recruited subjects at each time period (n = 1870) as well as subjects examined twice and compared over time regarding health indicators (n = 734). Diet was assessed through a validated food frequency questionnaire. Three healthy diet indices were calculated and related to 29 food groups. We also performed prospective regression of food group consumption with health indicators. Results: The diet over the time period of observation was very stable and consisted of a high proportion of vegetables, fruit and grains. No major changes in body mass index (BMI) and blood pressure were observed. Consumption of low-fat dairy, juices, olive oil, and water were related to reductions in weight gain, systolic blood pressure, high-density lipoprotein (HDL)-cholesterol and cholesterol (total and HDL) levels, in that order. Over the time periods we observed only a slight decrease of adherence to the Meddietscore. The correlations of the healthy diet indices with food groups revealed some differences among the indices, mostly regarding the intake of fruit and vegetables. Conclusions: The dietary pattern of Apulia is in line with many principles of a healthy diet and the cohort population seems to be less liable to undergo a transition to a westernized diet.