The kids wake up early in order to leave before anyone might come by the house; they head out to eat breakfast and make a plan for getting across the Bay.
After they eat, the Tillermans walk around Annapolis. The town is nice and the people are friendly, and no one bothers the kids.
At an army-navy supply store, Dicey buys a saucepan, ponchos, hooks, fishing line, a canvas backpack, and a jackknife. Outside, she unloads everything into the backpack, which is way easier to carry.
The kids mill around town for a while, then head toward the water. There, they see two teenaged boys scrubbing down the deck of a sailboat; the boys start splashing water on each other and get some on Dicey, so she shouts at them.
The boys—whose names are Tom and Jerry—apologize and invite her and her siblings on the boat to dry off. Once they're on board, the boys offer them towels and some Cokes.
It seems that the boat belongs to Jerry's dad—they're just working on it. At least until they turn sixteen, that is, at which point dear old dad is going to have to pony up and start paying them.
Dicey asks if they can go sailing whenever they want, and they say no really… though it's clear they do anyway.
James starts asking all kinds of questions: Is Jerry a good sailor? What does his dad do? Does he ever go to the eastern shore? All of Jerry's answers are kind of boastful, and Dicey can tell he's lying, but James acts impressed anyway.
Then James mentions that they have to get to the eastern shore of the Chesapeake Bay tomorrow. They were going to take a bus, but it would be really cool to sail, wouldn't it?
Yeah, Tom agrees, it would be, but Jerry can't really take out the boat without his dad's permission. Right, Jerry?
Well, Jerry counters, if they really want to go over, he can take them—he's totally up for a day of sailing if they are. Awesome. They agree to meet back at the boat at 8 a.m. tomorrow.
The Tillermans mentally high five as they leave. James is pretty impressed with himself and his powers of manipulation, though Dicey points out that Tom helped, too.
James wonders why one friend would do that to another.
That night, they feast on Burger King and James asks about their grandmother. What will she be like? Is she crazy like Momma? Dicey certainly hopes not. Though maybe all families are a little bit crazy in their own way. That's probably true.
Before they go to sleep, Dicey counts their money: They have forty-seven dollars left. She figures they should hold onto the last forty bucks until they get to Crisfield—make that if they get to Crisfield. Fingers crossed.