K.C.
Hi J.,
I had to move my son to a toddler bed when he turned 18 months old. While I thought this was very early, my son is very tall and the same as you I caught him with one knee up on the rail of his crib. I decided then that I would rather him be safe than to fall out of his crib onto the hard wood floor. The first night or two there were no problems getting him to sleep in the bed. It was new and exciting and he loved it! After that I found that for about 2 weeks it was a struggle to put him to bed. What worked for us is that he got to pick his favorite book each night and take it into his big boy bed with him. I would sit on the floor right next to the bed and we would talk about what was happening in the pictures (he won't sit still for story telling). By the end of the book he had to lay down I would rub his back for 5 minutes until he was good and sleepy. Then I would leave and he would go to sleep on his own. Ever since then when it's bedtime he takes my hand, we walk into his room and he climbs into bed all on his own! I never had a problem with him trying to get out though. For whatever reason, once he's in his bed (there is a toddler rail) he stays there until you come to get him. At night I do put up a gate in his doorway. I did have a fear of him waking up and walking around at night while we were sleeping, but it hasn't been a problem at all.
Good luck to you!