Women constitute a majority niche within the senior tourism segment, requiring more comprehensive understanding through research and by stakeholders in the tourism industry. It is essential to consider the characteristics of these tourists to determine their influence on travel planning concerns and the subsequent impact on satisfaction with the destination. In this study, based on a sample of 529 senior tourists who visited the Azores, three key components concerning the degree of importance attributed to travel-related concerns were identified, through Categorical Principal Component Analysis (CatPCA). Using a Partial Least Squares–Structural Equation Model (PLS-SEM), the study found that women’s education levels significantly influence their travel planning concerns. Specifically, the higher the education level, the less importance these tourists attributed to such concerns. It is important to note that the type of travel concerns among senior women can vary based on their characteristics. Understanding these differences allows professionals in this market segment to provide more personalized support, enhancing the well-being of these tourists.