This study aims to assess the patterns of life satisfaction with life (SwL), sexual satisfaction, and adjustment to aging (AtA), of older adults in Mexico and Portugal. A sample of 658 older adults, aged 65 years-old and older, from Mexico and Portugal were recruited for this cross-cultural study. The following measures were applied: (a) Adjustment to Aging Scale (ATAS); (b) Satisfaction with Life Scale (SwLS); (c) New Sexual Satisfaction Scale (NSSS); (d) Mini-Mental State Exam; and (e) Sociodemographic, health and lifestyle questionnaire. Clusters were identified and characterized by using K-means cluster analysis, encompassing SwL, AtA, and sexual satisfaction. Sexual well-being differences among clusters were analyzed with One-way ANOVAs. Findings indicated three clusters, which explained 76.4% (R-sq = 0.764) of the total variance: Cluster #1: “Moderately adjusted older adults” (n = 355, 53.9%), Cluster #2: “Moderately fulfilled older adults” (n = 265, 40.3%), and Cluster 3: “Well adjusted and satisfied older adults” (n = 38, 5.8%). Participants in Cluster #1 were mostly Mexican, with moderate levels of AtA and reduced sexual satisfaction and SwL. Conversely, Cluster #2 predominantly consisted of Portuguese participants with moderate sexual satisfaction and SwL, and lower levels of AtA. Participants from Cluster #3 were mostly Portuguese with high levels of AtA, sexual satisfaction, and SwL. This innovative study explored the intricate relationship between sexual well-being, the ability to adjust to aging, and overall SwL, in two different cultural contexts. Findings contributed to the understanding of the relationship between these three variables and for developing tailored future interventions and service planning with older adults in different cultures.