perfect opportunity to get things started, need help making it happen

My wife planned a ski trip a few months ago tha

Sounds like you have a good plan. But - I would put the condoms in a padded envelope so she does not know what's in the envelope. I would also put a note in the envelope that said "I'm glad your getting your time away - now make the most of it, and that means this envelope should be empty when you return and you should have plenty of stories ( and if I'm really lucky a few pics) to share! I love you!"

That's my recommendation.

I'm thinking the sexy pajamas should do the trick. And I would make the note attached to the condoms say "Don't forget to use protection" which gives her the knowledge that you know she is going to do it and you only want her to be protected (even if you really wish she would forget the condoms). I am sure both items will cause her to have a phone converstion with you about what you think she would do, at which point you reassure her again that "It's perfectly OK."