Tax compliance and avoidance are critical issues for governments and businesses worldwide, especially as businesses often use legal methods to minimize taxes, which can impact public revenue and equity within the tax system. This study focuses on understanding the factors influencing tax avoidance behaviors among SMEs in Greece’s tourism sector, a sector that has received limited research attention. To this end, a quantitative cross-sectional design was employed, using a structured questionnaire to explore potential factors influencing tax avoidance behavior. Data were collected from 534 SME managers and analyzed using Structural Equation Modeling (SEM) to assess the impact of key factors and their interrelationships, including coercive power, digital transformation, tax knowledge, firm performance, and perceived fairness, on tax avoidance. In addition, corporate social responsibility (CSR) was included as a moderator variable, while coercive power and digital transformation were assessed as mediators. Furthermore, Multi-Group Analysis (MGA) was conducted to explore the differences between small and medium enterprises, as well as different ownership structures. The results indicate that all key determinants, except perceived fairness, are significantly and positively related to tax avoidance intention. Additionally, it was revealed that coercive power increases tax avoidance through firm performance and tax knowledge, while digital transformation mediates the influence of firm performance on tax avoidance by curtailing avoidance intentions. While CSR mitigates the negative influence of coercive power, digital transformation has a dual role: that of promoting transparency and strategic efforts to reduce the tax burden. These findings have important policy implications, as policymakers seek to promote digital adoption and enhance CSR engagement while formulating specific regulatory strategies to reduce tax avoidance among SMEs.