Skills’ development is considered as one of the most important drivers of productivity growth and competitiveness at the enterprise level. Employers, academics, and policymakers have recognized the importance of social and professional skills as valuable qualities for a successful career in all sectors of the economy. In Greece, the tourism sector is considered as a key factor for the development of the country and its economic progress. It is also assumed that the human factor in tourism, in the form of service personnel, is critical for the success of a business and conducive to the general favorable evaluation of a destination. The present study combined the skills’ narrative with secondary research data analysis from the tourism sector, and quantified the influence of skills development on the evaluation of the destination and the vacation experience acquired. The findings bear important implications for marketing, management, and educational issues in tourism.