Objectives: Patients with acute respiratory failure due to coronavirus disease 2019 (COVID-19) have a high likelihood of needing prolonged intubation and may subsequently require tracheotomy. Indications and timing for performing tracheotomy in patients affected by severe COVID-19 pneumonia are still elusive. The aim of this study is to analyze the role of tracheotomy in the context of this pandemic. Moreover, we report the timing of the procedure and the time needed to complete weaning and decannulation in our center. Methods: This retrospective, observational cohort study included adults (≥18 years) with severe COVID-19 pneumonia who were admitted to the intensive care unit (ICU) of the tertiary care center of Reggio Emilia (Italy). All patients underwent orotracheal intubation with invasive mechanical ventilation, followed by percutaneous or open surgical tracheotomy. Indications, timing of the procedure, and time needed to complete weaning and decannulation were reported. Results: Forty-four patients were included in the analysis. Median time from orotracheal intubation to surgery was 7 (range 2-17) days. Fifteen (34.1%) patients died during the follow-up period (median 22 days, range 8-68) after the intubation. Weaning from the ventilator was first attempted on median 25th day (range 13-43) from orotracheal intubation. A median of 35 (range 18-79) days was required to complete weaning. Median duration of ICU stay was 22 (range 10-67) days. Mean decannulation time was 36 (range 10-77) days from surgery. Conclusions: Since it is not possible to establish an optimal timing for performing tracheotomy, decision-making should be made on case-by-case basis. It should be adapted to the context of the pandemic, taking into account the availability of intensive care resources, potential risks for health care workers, and benefits for the individual patient.