I have twin boys, and we had to transition at 25 months because they were climbing out of their cribs. We made a big deal out of the whole thing. Brought them to the store with us, let them "help" pick out their sheets, wave "bye bye" to the cribs. You get the idea. The first night was hilarious. They clearly thought they were getting away with something. We just closed the door and let them run amok (the room is kid-proofed, so all they can do is make a mess). When the crying started, we went in and asked them if they would like us to cover them up before they went "night night". They were so wiped out at that point, they pretty much drifted off to sleep before we were done. Since then, we have a bedtime ritual of pjs and stories, then covers go on and everyone gets kisses. After a couple of rounds of covers and kisses, they usually fall asleep on their own. After a week we noticed there was more night waking, so we brought back out their turtle night light so there would be some light. That made a big difference. They pretty much settle themselves back down now like they did with their cribs. The boys are 27 months old this week, and we find we don't miss the cribs at all.