Background The decision to consent to surgery is a life-changing moment. This study addresses the impact of total laryngectomy (TL) on phonation and its effect on the quality of life (QoL) of patients. The primary objective of this cohort study is to compare the alternatives in phonation rehabilitation, and the secondary objective is to identify concurrent predictors of vocal outcomes. Methodology To perform a comprehensive analysis, we reviewed data from patients who underwent TL with bilateral radical neck dissection in the Department of Otolaryngology, Head and Neck Surgery at Centro Hospitalar Universitário de Santo António between January 2010 and October 2022.Adult patients who consented to participate in the study and underwent subjective evaluation were included in this study. Data regarding clinical history was primarily collected. Statistical analysis was performed using SPSS version 26 (IBM Corp., Armonk, NY, USA). Different types of vocal rehabilitation formed the subgroups to be compared. An additional analysis was performed for baseline variables collected in the clinical records, and vocal outcomes were measured using the Self-Evaluation of Communication Experiences After Laryngectomy (SECEL) questionnaire. Furthermore, linear models taking SECEL scores as the outcome were developed. Results The first search identified a total of 124 patients operated during the study period. In total, 63 patients were alive at the time of the current follow-up, with 61 deaths (49%). Overall, 26 of the 63 alive patients completed the SECEL questionnaire. All patients were male. The mean age at diagnosis was 62.2 ± 10.6 years. The mean age at the time of subjective vocal assessment with the SECEL questionnaire was 66.3 ± 10.4 years. The mean time of follow-up after the initial diagnosis was 4 ± 3.8 years. A statistically significant difference was observed in esophageal speech (ES), which was inferior to other modalities (mean SECEL total score for ES: 46.6 ± 12.2 vs. mean SECEL total score for all other modalities: 33 ± 15.1; p = 0.03). The follow-up time correlated significantly with vocal function, as measured by the SECEL questionnaire (p = 0.013). Conclusions The SECEL questionnaire can be a valuable tool to evaluate QoL in laryngectomy patients, given its usefulness in assessing the psychological impact derived from vocal functionality in this group. ES appears inferior to other modalities regarding voice-related QoL.