Vacations offer a break from daily stressors but at the same time introduce challenges away from home. While the positive aspects of vacationing, especially individual benefits, are well documented, the challenges couples face and their psychological mechanisms and outcomes remain unexplored. This study investigated the effects challenges and challenge resolution might have on shared experiences and on relationship quality. We collected data from 100 romantic couples at major tourist destinations in the Netherlands in Spring 2024. Random intercept regression models showed that novelty is positively associated with positive emotions, passionate love, and feelings of connection with partner; and that challenges would take away some of these benefits. Interestingly, challenges were associated with self-expansion, a major predictor of long-term love and passion, especially when partially resolved. Positive emotions mediated some of these relationships. These findings highlight the importance and value of studying challenges and challenge resolution on vacations for relationship and experience quality.