Contemporary lifestyles and social changes have precipitated the popularity of solo travel. Despite the growing prominence of the solo travel market, it remains an under researched area. This study explores the definitions, motivations, and constraints of solo travel, taking into consideration both existing and potential solo travellers, and provides a gender-balanced investigation and subsequent in-depth understanding of the underlying factors that drive solo travel motivations and constraints. Interviews were conducted with 14 solo travellers and 14 non-solo travellers. The findings suggest that solo travel as an evolving and fluid concept, varies according to individual travel experiences and personal circumstances. Solo travel motivations can be broadly categorized into ‘solo by circumstances’ and ‘solo by choice’. Transformative experience, freedom, and flexibility are key motivators for solo travellers, while anticipated self-discovery and freedom inspire the potential solo travellers. Safety, cost, and social constraints emerged as the top three inhibitors impeding or constricting solo travel participation and experience. The findings reveal the institutionalization of solo travel and proclivity to join tours as strategies to build confidence and overcome safety and social constraints. Recommendations for the travel industry to cater to the solo travel market were also examined from the travellers’ perspectives.