This case study assessed the psychological strengths and stability of attitudes and values of a 29-year-old male who successfully completed a 260-day solo sailboat circumnavigation of the globe. Personality findings indicated positive psychological functioning; high scores on traits of boldness, agreeableness, and openness; and mid-range on extraversion. An internal locus of control belief orientation was evident from the pre- to post-voyage evaluation periods. Personal values of hedonism, universalism, and stimulation were the highest rated values over the course of the voyage. Positive adaptation was reflected in perceptions of personal growth, endorsement of positive experiences, and flexibility in using a variety of coping strategies depending on the situation. The mid-range level of extraversion and high trait agreeableness may be adaptive characteristics, reflecting comfort in solitude while possessing the ability and interest in communicating with others as a means of stimulation and social support.