Possible Clues:

• Set sail before a bird embraces pussycat's tail
• Emulate Columbus
• Turn jack over — so get, unexpectedly, ace
• Understood prophet not the first to live off the land
• Proceed to watch, it's said, what sailors do
• Run over side, almost, clutching extremely big sail
• Set sail, turn craft east heading for Okinawa
• Become a sailor who had obtained ring main