Jarvis famously sailed alone around Lake Ontario, from Hamilton to Niagara-on-the-Lake to Whitby and back, in a tiny dinghy aptly called "Tar Pot" when he was just twelve years old. (This journey was reported in newspapers at the time, beginning the legend of the sailor.) Later in life, he spent two years sailing the world in a square-rigger sailing vessel. He designed and built numerous innovative and successful racing sailboats, founded the Royal Hamilton Yacht Club, and was a longtime member of the Royal Canadian Yacht Club, of which he was elected commodore seven times. He won the inaugural Canada's Cup yachting race in 1896 sailing the "Canada", a 57-foot cutter. Additionally, he won over 100 international freshwater sailing events while at Royal Canadian Yacht Club (& more than 300 overall), including a second Canada's Cup in 1901.