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Background: Clinical electives, provide opportunities to inform future career paths.  The primary purpose of this study was to examine whether the clinical electives were being used as intended i.e. to help with specialization choice and  to determine the factors that influence trainee decisions for specialty training at The University of the West Indies. Methods: A cross-sectional study was conducted between July 2019 and March 2020, using a self-administered questionnaire.   Results:  193 participants completed the questionnaire, aged 20 to 35 years, 133 (68.9%) were females.  The most common electives completed were internal medicine specialties (80, 41.5%), followed by surgical specialties (53. 27.5%). Only 64(33.2%) participants reported electives used to gain experience for future career; other reasons included filling knowledge gaps (101, 52.3%), having to repeat failed clerkships (19, 9.8%). Future career preferences were the specialties of  surgery (75, 40.8%), internal medicine (41, 22.3%), anaesthetics (20,10.4%) and obstetrics & gynaecology (18, 9.3%). Males showed a preference for surgical specialties (p=0.002). The use of the elective for determining career path showed significant correlation with future specialty choice (Likelihood ratio chi-square test (32) = 98.37, p<0.001).  Career motivation factors correlating significantly with future specialty choices were intellectual challenge (p=0.025), income (p=0.010), prestige(p=0.015) and working hours(p=0.012). Conclusions:  There was use of clinical elective rotations as intended by  senior medical students and junior doctors. Surgical specialties were the top selections especially for males. Career counseling was needed to guide beneficial use of the clinical electives and to encourage the alignment of specialty choice with trainee  motivations.