Overcome with “Klondike fever,” Jack departed from San Francisco on the SS Umatilla on July 25, 1897, accompanied and bankrolled by his much older brother-in-law, Captain Shepard. They sailed to Port Townsend, Washington on Upper Puget Sound, where they boarded the SS City of Topeka which took them to Juneau Alaska.
The SS Umatilla was a steamer of the Pacific Coast Steamship Company, which sailed from San Francisco to the Pacific Northwest. A prior SS Umatilla had been sunk in 1884. The ship shown below was still in operation as of 1913, but little is recorded of her origins or disposition.