This study examines Finnish apprenticeship training stakeholders' perceptions of vocational expertise and experiences of workplace learning and guidance. The semi-structured interview data was collected in 2015 in two vocational fields: the social and health care services sector (five workplaces) and the technology sector (five workplaces). The sample (N = 40) consisted of apprentices (n = 10), their co-workers (n = 10), workplace trainers (n = 10) and employers (n = 10). The study applies the classifications of natural abilities and self-regulation to identify the most important individual characteristics related to vocational expertise. The socio-cultural approach to workplace learning and guidance illustrate that vocational expertise also develops from external support through participation and guidance in everyday interactions in the contexts of education and work. The data was analysed using qualitative content analysis. The findings indicate that individuals with fluent cognitive skills (e.g., problem solving skills) combined to advanced social skills, self-awareness and self-regulation are perceived as vocational experts. The apprenticeship training was considered to draw upon an extensive learning environment to facilitate an apprentice's vocational development by offering access to authentic work tasks and collective support by experienced workers. Yet, the lack of time, resources and pedagogical approaches were found to hinder individual guidance and reciprocal workplace learning between apprentices and experienced workers. The workplaces were shown to provide fruitful learning possibilities for those apprentices with strong self-regulatory skills.