Background: Recommendation from doctors is a well-recognized motivator toward vaccine uptake. Family doctors are in the prime position to advise the public on COVID-19 vaccination. We studied the practice and concerns of frontline family doctors concerning COVID-19 vaccination recommendations to patients. Methods: We conducted a cross-sectional online survey of all family doctors in the Hong Kong College of Family Physicians between June and July 2021. Their practice of making COVID-19 recommendation to patients was assessed. Based on the Health Belief Model, factors associated with doctors’ recommendation practices were explored and examined. Multivariate logistic regression models were used to investigate the factors, including COVID-19 vaccine attributes, associated with doctors’ practices in making recommendations. Their own vaccination status and psychological antecedents to vaccine hesitancy were measured. Results: A total of 312 family doctors responded (a 17.6% response rate). The proportion of doctors who had received COVID-19 vaccines was 90.1%. The proportion of doctors who would recommend all patients without contraindications for the vaccination was 64.4%. The proportion of doctors who would proactively discuss COVID-19 vaccines with patients was 52.9%. Multivariate logistic regression analysis showed that doctors’ own COVID-19 vaccination status was the strongest predictor of family doctors making a recommendation to patients (aOR 12.23 95% CI 3.45–43.33). Longer duration of practice, willingness to initiate the relevant discussion with patients and less worry about vaccine side effects on chronic illness patients were the other factors associated with making a COVID-19 vaccination recommendation. Conclusions: Family doctors should be encouraged to get vaccinated themselves and initiate discussions with patients about COVID-19 vaccines. Vaccine safety data on patients with chronic illness, training and guidelines for junior doctors may facilitate the COVID-19 vaccination recommendation practices of family doctors.