The sky begins to cloud just as night falls, dropping the temperature enough that bikinis are no longer the deck wear of choice. So far, the sail has gone exactly to plan, the spells smooth, the weather just right, and the puppets competent enough to handle the sail without needing to use up the summons.
He can call nine different supporters now, with two spots currently occupied by the pairs of Sailors and a spot by the Spider Queen. Having two water and two wind-type casters works out very well for them. They can push their speed a little, knowing that they've got a backup, and they can swap out when they get bored.
Cain decides to pull a pair of maid-type puppets out of his inventory before dinner, having them prepare and plate everything. They've got ready-made meals in their inventory still, expecting some busy days without time to cook, and since they got started late, Cain decides this is one of them.