COVID-19 has changed people’s routines and imposed new ways of living. This study investigated variations in lifestyles (namely, physical activity, diet, alcohol consumption, and cigarette smoking) between the prepandemic and the pandemic period in a sample of older adults with hypertension. Moreover, it investigated predictors of adherence to government restrictions during the first lockdown period, evidencing the role of relevant sociodemographic indicators and lifestyle changes. A sample of 105 older Italian adults (M_age = 70 years; SD = 5.83) with hypertension was enrolled from a previous longitudinal study and interviewed on the phone between May and August 2020. Updated information about sociodemographic indicators and lifestyle changes was collected. Adherence to restrictions was explored through several questions regarding compliance with home confinement, facemask use, and the observance of social distancing. Results evidenced that only 33% of the respondents abided by all the national restrictions. During the first pandemic peak, considerable changes in lifestyles occurred, particularly regarding physical activity, which diminished in 70% of the sample. Women, unemployed/retired people, and individuals who decreased their amount of physical activity reported higher adherence to rules. Maintaining a healthy lifestyle over time is essential for disease prevention. Therefore, it is essential to continue to inform the population about the importance of a healthy lifestyle, and it is necessary to provide guidelines to maintain and promote it even during housebound periods.