Gentle weaning- how to?

I am 8 weeks pregnant with my 3rd child, currently nursing my 10 month old. My OB has told me I need to have him weaned going into my second trimester, as I have an established history of preterm labor with both my previous pregnancies. As much as I wish I could continue nursing him, it just does not seem to be in the cards for me. He will be about 11 mos 1 week when we finish(maybe a week or two later) and I'm glad to have made it this far. So at this point I have about 5 weeks left.

My question at this point is how do I make the transition as easy as possible on him? I have started upping his solids intake to 3x a day now, and he is starting to take the cup better and better. How do you handle bedtimes though? He is used to me nursing him down, and I refuse to do the CIO thing. Any help would be greatly appreciated, I am so worried about how we will handle this