(1) Background: Lifestyle changes, eventually coupled with a nutraceutical, are recommended strategies for managing high–normal blood pressure (BP) patients with low–moderate cardiovascular (CV) risk. In a real-life clinical setting, we evaluated the effects of generic written lifestyle advice, extrapolated from the 2018 ESC/ESH guidelines, and a beetroot-based nutraceutical on 24 h BP in a population with a high–normal office BP and low–moderate CV risk. (2) Methods: A longitudinal observational study was conducted in two ESH Hypertension Excellence Centres on 43 consecutive subjects with high–normal BP according to repeated office BP (OBP) measurements and a low–moderate CV risk based on SCORE2/SCORE2-OP. Additionally, 24 h ambulatory BP monitoring (ABPM) was carried out at baseline and three months after lifestyle changes, according to generic written advice from the 2018 ESC/ESH guidelines, coupled with a nutraceutical containing 500 mg of dry beetroot extract. (3) Results: The mean age was 50 ± 11 years, with male prevalence (54%). The prevalence of overweight/obesity was 58%. The mean OBP was 135 ± 3/85 ± 3 mmHg. At baseline, the mean 24 h BP, daytime BP, and night-time BP were 127 ± 7/80 ± 6 mmHg, 131 ± 8/83 ± 6 mmHg, and 118 ± 8/70 ± 5 mmHg, respectively, BP profiles compatible with hypertension status in some subjects. After a median follow-up of 98 (92–121) days, all BPs, except night-time diastolic BP, were significantly decreased: −3 ± 6/−2 ± 4 mmHg for 24 h BP, −3.9 ± 6.0/−3.0 ± 4.0 mmHg for daytime BP, and −3.3 ± 7.4/−1.3 ± 4.7 mmHg for night-time BP, respectively. No significant clinical changes in body weight were detected. BP decreased independently of baseline BP levels, sex, smoking status, and body mass index, while a more substantial BP decrease was observed in older patients. (4) Conclusions: Our exploratory study shows, for the first time, that written generic lifestyle advice taken from the ESC/ESH hypertension guidelines coupled with a beetroot-based nutraceutical may represent a valid initial non-pharmacological approach in subjects with a high–normal office BP and low–moderate CV risk, even without personalized diet interventions.