Oregon Man Sails to Hawaii, Celebrates Dream with Cat

WAIKIKI, Hawaii — Oliver Widger, a 29-year-old from Oregon known as @sailing_with_phoenix on TikTok, arrived in Hawaii on Saturday after a daring journey across the Pacific Ocean. Widger’s adventure began in late April when he decided to quit his job, empty his 401(k), and sell all his belongings to chase his dream of sailing.

He completed the 24-day trek on his $50,000 sailboat alongside his cat, Phoenix. Upon his arrival at the Waikiki Yacht Club, he was greeted by ecstatic fans and received an official proclamation from Governor Josh Green.

“Dear Corporate America, I won,” Widger declared in a celebratory Instagram post after docking in Oahu.

Widger initially worried he might not handle the large crowd but described the experience as exhilarating. “I had to hold on to things to not fall over,” he admitted.

With more than 1.7 million followers on Instagram, Widger has shared his sailing journey and connected with many who share a desire to break free from the daily grind. “I think a lot of people are grinding at their jobs, and it doesn’t really matter how much money you make. Everybody’s just trying to do enough to get by,” he said.

The decision to sail stemmed from a significant health diagnosis last year. Widger suffers from Klippel–Feil syndrome, which puts him at risk of paralysis. “Hearing that kind of just shook up my world,” he reflected.

He sold his possessions, trained himself to sail through YouTube videos, and set off on this ambitious voyage despite lacking formal sailing experience. Throughout his journey, he managed to stay connected with friends via technology, alleviating feelings of solitude.

The hardest moment during the trip was when his rudder failed. Widger now tentatively plans to sail to French Polynesia but must first make repairs to his boat.

Governor Green praised Widger’s spirit, stating, “With no formal training—just courage, curiosity, and a whole lot of heart—Oliver set sail in search of something deeper.” Widger’s venture echoes the innate human drive to explore and trust in the vastness of the ocean.