A.J.
Unless he is climbing out, I say keep him in the crib. That is what we did/are doing with our children. We moved our oldest out of her crib when she was 3 and she has been good about staying in her room. Our littlest will be 3 this summer and we plan to do the same thing. No reason to hurry it up, in my opinion ;)
But if you must get him out for safety or other reason, just keep his gate up and know it will take some time for the newness and excitement of the freedom to wear off. Be extra sure to get him outside and let him run (yes, even in the winter) and talk with him about the rules of his new bed. For our home, once my oldest was in her big bed I told her she did not have to sleep but she did have to stay in there and play with a select few toys I allow in there. I don't let her turn on her own light at night so she will be more likely to fall asleep quickly. It's easy now that it's dark so early :)
HTH! Merry Christmas!