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Armed with one small bag, credentials from the German Embassy in Washington, two copies of the statement from the Clan, and several copies of The Gaelic American, Kenny set sail from New York August 21, 1914 on board the S.S. Canopic, headed for Naples. The ship ran at night without lights, from fear of German cruisers, compelling passengers and crew to go to bed in the dark. The waters surrounding the ship were filled with British warships - "low, dark and rakish(?)". The ship abruptly changed course one night - due most likely to the presence of German ships.

The trip was fraught with tension. The shipping lines had used the pretext of war as an excuse to raise the rates and lower the service. Steerage was packed, while first and second class were empty. The fare was poor, and they were subjected to continuous war reports. Keeping to himself, John Kenny passed the time observing the diverse population of both the crew and the passengers.

As they approached Gibraltar the tension mounted. There had been rumors that neutral ships were being boarded and searched by the British. The S.S. Canopic passed through Gibraltar unchallenged but they were not yet safe. A British torpedo boat ran alongside for quite some time, with a constant interchange of signals, before finally veering off to John Kenny's immense relief.

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