The Bupp family, hailing from Florida, has embarked on a remarkable journey that many dream of—a complete circumnavigation of America’s Great Loop, a 6,000-mile boating route. In an exclusive interview with PEOPLE, Joanna and Kevin Bupp shared the motivations behind their big adventure, which includes their two children, Jackson, aged 12, and Julian, aged 10.
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For over two decades, Kevin, 47, had envisioned travelling the Great Loop, which traverses the United States’ eastern seaboard, winds through the Great Lakes, and navigates various rivers leading into the Gulf of Mexico. Although traditionally this expedition is favoured by retirees, the Bupps decided to take on the challenge as a family. Initially, they believed their journey would begin once the children were in college, allowing them a more traditional schooling experience until then.

Earlier this year, however, a conversation changed everything. Joanna approached Kevin with the realisation that life is unpredictable and that waiting was not an option. “She was like, ‘You’re the one who always says we’re not promised tomorrow, right?’” Kevin recounted. They believed their children were at an age where they could benefit from a unique educational experience, and so the idea was set in motion.
Before diving headfirst into the expedition, the pair needed to gauge their children’s feelings about leaving behind friends and sports teams. They proposed the idea of homeschooling on the water, highlighting the prospect of a shorter school week and extended weekends. Kevin noted that the boys quickly embraced the idea: “They’re already ahead of probably their peers,” he remarked, suggesting that their enthusiasm stemmed from the allure of a flexible learning environment.
With everyone in agreement, the Bupps faced the daunting task of preparing for their adventure. The family needed to find a suitable boat that could accommodate four family members, their dog, and enough space for both educational and work purposes. The logistics involved proved more intricate than anticipated, as they navigated through various issues including insurance and necessary certifications.
In addition to securing a vessel, the family had to address mundane but essential tasks, such as mail management during their year-long trip. “We kept pushing our departure date further back due to unforeseen issues,” Kevin explained. “Eventually, we realised there would always be something to fix. So we decided it was time to just go.”
Since embarking on their adventure, the Bupps have experienced relatively smooth sailing, though they swiftly discovered that life on the water is far from a vacation. Daily responsibilities involve monitoring weather conditions, planning routes, and identifying potential hazards along their journey. “It’s not just about lying around in the sun; there’s a lot of organising that goes into this,” Kevin emphasised.
On the educational front, Joanna enlisted the help of a friend back home to facilitate their homeschooling experience. This involved sourcing the right online programmes and ensuring that the children continue to meet their educational milestones. The family has also embraced their unique surroundings for hands-on projects, such as constructing a model boat from recycled materials and conducting water tests.
The Bupps are keen on encouraging other families who might be contemplating a similar journey. Joanna’s advice is succinct: “Don’t hold off. It’s so doable.” She acknowledges that different families will face various challenges—be it work commitments, travelling with pets, or managing children’s activities—but she believes those can be worked around. The essence of her message is clear: adaptability is key, and the trip can be tailored to fit any family’s needs.
As the Bupp family continues their odyssey around the Great Loop, they not only expand their horizons but also create cherished memories together. This journey, which combines adventure with learning, underscores the transformative potential of stepping outside one’s comfort zone and embracing the unknown.
