Caillou and family go on a trip on Helen's boat, an old friend of Mom's. Caillou is surprised to find there's a whole house packed into the boat. Caillou learns about wind and sails, and even gets to steer the boat too! When Mom and Dad are getting ready to go out to a restaurant, Caillou doesn't understand why he can't go too! He's disappointed until Julie the babysitter suggests they make their own restaurant, complete with menus! When Caillou accidentally breaks one of his toys because his room is a mess, Mom suggests a way to make cleaning up fun: with colourful stickers and a chart. Now Caillou and Rosie get to pick out their very own stickers for brushing their teeth and cleaning up the toys in their bedrooms! When Caillou dresses himself, he learns that when you put your pants on backwards, you can change and put them on right. When he sees Dad and Grandpa in suits and ties for a big party, he changes into his grownup clothes too. Jonas, a friend of Dad's and a real cowboy, has invited the family to visit his ranch. Caillou had never met a real cowboy before. Caillou learns a lot about horses; he gets to brush a pony named Lucky, he even gets his very own cowboy hat!
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