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John Cabot On March 5 , 1496 King Henry gave John Cabot a charter giving him permission to sail North, East or West but not South because that is where the Spanairds were to search of new land. John Cabot set out on his first voyage on May 2, 1497, a year later, from Bristol Harbor. John had a ship called the Matthew, named after his son, which sailed from England and had a crew of 18 men. They headed northward for a short while sailing past the tip of Ireland, then they turned and started sailing wes