For Dr. Livesey and his friends, the second trip to shore is much harder. Five men have to ride in a small boat with a great deal of food and ammunition. The boat is so overloaded that it can hardly stay afloat. To make matters worse, the tide is going out, so it is very hard to make progress toward shore. The doctor, who is controlling the rudder, finds that he has to steer at a right angle to the direction he wants to go; if he did not, the boat would get swamped.

As the men struggle with their overloaded boat, they suddenly realize that they have made a serious mistake. They took or destroyed all of the weapons that could easily be moved ashore, but in their hurried preparations, they did not destroy the ammunition for “the long nine”—a big cannon on the Hispaniola. They look back to the ship and see that the mutineers they left on board have noticed the error. They are already loading the cannon to take a shot.

Mr. Trelawney is the best at shooting a musket, so the men stop rowing and hold the boat steady while Trelawney takes a shot at the pirates. He aims at Israel Hands, the man his friends know to be the most skilled with heavy weapons. Unfortunately, Hands bends down at the last moment, and Trelawney’s bullet hits someone else. This poor man does not die, but his comrades do not help him. Instead, they continue their hurried preparations with the cannon.

As all this is happening, the captain’s men see several of Long John Silver’s mutineers running along the shore. These men climb into one of their small boats and begin to row toward the captain’s men. They are no great threat; they are fighting the tide, so it is clear they will not arrive quickly. However, the cannon is almost ready to fire.

The captain tells the doctor to steer straight for shore, even if the boat takes on water. The doctor obeys, and he makes fairly good progress until the cannon fires. The captain’s men dive out of the way, and the cannonball flies over their heads. However, in all the jostling, the boat gets swamped.

Only the doctor and the captain have the presence of mind to keep their muskets out of the water; three guns get dunked in the sea, as does the whole boatload of food and ammunition. Now half of the supplies are lost, and three of the muskets will not shoot. They run to shore, hoping they will arrive at the stockade before Long John Silver can organize his pirates for an attack.