K.,
Just go for it! He's ready. Mine was 22 months old and climbed out of the pack n play at GRANDMA'S!!! It was our first day there, too, and we were going to be there for 2 weeks! I didn't know what to do and thought it was going to be terrible, but we just threw a twin mattress on the floor, cleared out the room of safety hazards, and let him sleep. He did GREAT! When we got home, we went out right away and purchased a toddler bed. He's been in it ever since. He's always been good about staying in it (we're really lucky) but when he has gotten out at bed/naptime, we use the Supernanny technique of going in there, picking him up, putting him back in bed, and leaving the room - all without saying a word. If he kept getting out (over three or four times) we would say, "It's night night time. You need to stay in bed," then leave the room. You really have to be consistent with this. Either way, if he's crawling out of the crib, he's ready for the toddler bed. Chances are, he'll be so excited about the new bed, you won't have too many problems. Good luck!
Amy K