Roland Wilson, 31, from Stanley in Perthshire, is alleged to have been negligent after the boat called Atalanta of Chester strayed into a marked shipping lane as a 120,000-ton oil tanker Hanne Knutsen sailed past on the first day of Cowes Week in August 2011.
The 33ft racing yacht, carrying Mr Wilson and a seven-man crew, was taking part in a race for Cowes Week when it crashed into the side of the tanker and several crew had to jump overboard.
One person suffered a minor injury in the incident that was captured on video and posted on YouTube.
Wilson denies three counts of contravening maritime regulations.
The trial at Southampton Magistrates' Court is expected to last six days.