We let our daughters sleep swaddled until around 6 months, when they really couldn't be contained anymore and/or started rolling over (still swaddled) in their sleep. LIke others have said, I'd switch to the crib first, then tackle the swaddling when it's really necessary. Take out one arm for a few nights (most likely he'll surprise you and sleep fine anyway); then once that's the norm for him, take out the other arm, but keep the blanket around the legs. This worked with both our daughters; we were really surprised what a non-issue it was, but again, we waited a little longer than you are.
at 5:00 PM on Jul. 16, 2009