Introduction The optimal time for tracheostomy changes is unknown. Most surgeons opt to wait until five to seven days postoperatively, while more recent studies suggest that changes occurring as early as two to three days postoperatively are also safe. Objective To evaluate the safety of changing the tracheostomy tube later than 14 days postoperatively. Methods The charts of patients who underwent tracheostomy placement and change at a tertiary care center from 2015 to 2019 were retrospectively reviewed, and the subjects were divided into 2 cohorts (late and very late), depending on the time of the first tracheostomy change. Results The study included 198 patients, 53 of whom aged between 0 and 18 years, and 145, aged > 18 years. The time until the first tracheostomy change was on average of 131.1 days. The most common indication for tracheostomy tube placement was prolonged intubation. Adverse events were observed in 30.8% of the cases (the most common being the formation of granulation tissue), a rate that does not differ much from the incidence reported in the literature (of 34% to 77%) when tracheostomy tubes are changed as early as 3 to 7 days postoperatively. There was no significant difference in the incidence of complications between patients undergoing late and very late changes ( p = 0.688), or between pediatric and adult subjects ( p = 0.36). There were no significant correlations regarding the time of the first or second change and the incidence of complications (r = -0.014; p = 0.84 for the first change; and r = -0.57; p = 0.64 for the second change). Conclusion The late first tracheostomy tube change was safe and could save resources and decrease the financial burden of frequent changes. It is always crucial to provide adequate information about home tracheostomy care for patients.