RedactedNarrative: O1 was attempting to load the vessel onto its trailer. During the loading process O1 was driving the vessel forward and the starboard side pontoon struck the vertical wooden guide on the trailer. Striking the wood guide broke the bolt that fastened it to the metal support post. As the boat traveled forward the support post struck the pontoon creating an approximately 10in whole on the inside of the pontoon. The pontoon started to fill with water and O1 along with family and friends present was able to winch the pontoon approximately halfway on the trailer so they could get the vessel out of the water. During the accident no one was wearing a PFD, but a subsequent boat safety inspection found enough PFD's and the boat properly equipped with the other required safety equipment.