Homeschooling families typically have the freedom to plan educational road trips without the constraints of a traditional school calendar. For this study, a total of 21 web pages were selected using ‘roadschool’ – a term that has recently emerged to describe such trips – as a keyword. A web content analysis revealed that this option is perceived as an opportunity for family bonding and is mostly popular among homeschooling families who own recreational vehicles and consider themselves digital nomads. Furthermore, it was observed that roadschooling parents often exhibited personality types that enhanced the overall learning outcomes and experiences of their trips. Implications and future research directions are discussed.