Background: Tracheostomy, as an aerosol-generating procedure, is considered as a high-risk surgery for health care workers (HCWs) during the coronavirus disease (COVID-19) pandemic. Current recommendations are to perform tracheostomy after a period of intubation of > 14 days, with two consecutive negative throat swab tests, to lower the risk of contamination to HCWs. However, specific data for this recommendation are lacking. Therefore, this study aimed to evaluate viral shedding into the environment, including HCWs, associated with bedside tracheostomy in the intensive care unit. Methods: Samples obtained from the medical environment immediately after tracheostomy, including those from 19 surfaces, two air samples at 10 and 50 cm from the surgical site, and from the personal protective equipment (PPE) of the surgeon and assistant, were tested for the presence of severe acute respiratory syndrome coronavirus 2 in eight cases of bedside tracheostomy. We evaluated the rate of positive tests from the different samples obtained. Results: Positive samples were identified in only one of the eight cases. These were obtained for the air sample at 10 cm and from the bed handrail and urine bag. There were no positive test results from the PPE samples. The patient with positive samples had undergone early tracheostomy, at 9 days after intubation, due to a comorbidity. Conclusions: Our preliminary results indicate that delayed tracheostomy, after an extended period of endotracheal intubation, might be a considerably less contagious procedure than early tracheostomy (defined as < 14 days after intubation).