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I left LO for 3.5 days when she was almost 3 months old. I would leave her for a week now at 9 months but I don't have anyone who can watch her for that long!

Honestly, I'd vote that if you aren't nursing you can go when he's 1 yr old so long as he is 100% comfortable with your parents and sister and they know how to deal with him.
What I mean by that is: because you have such an awesome babysitter: it makes sense. I'd trust my mom with my life and my son's and I think I would do it as soon as he was 1ish. Of course, if I didn't have someone as awesome as my mom to stay with him, or my MIL, then no---I wouldn't even think about leaving.
--I'd take him I guess haha

I've been wondering about this myself, so I'm following to see what people say.

I think a great first vacation might be to do a vacay with my Mom (and her boyfriend) along too so we can have some time alone, but also be together.

@coco bee - I was! I had bridesmaids stuff from 8 am til midnight and we were constantly on the move. now I am a nutcase about saving every drop, because the weekend away had me nearly all the way through my stash, which I haven't really been able to grown since...

I actually think it would be easier to start when the child is a little bit younger to get them used to being apart from mom and dad. My parents never left my brother until he was two and a half. They went away for a long weekend and left my brother with my aunt. Well... my brother just wandered my aunt's house the WHOLE time going "Where mommy go? Where mommy go?". He was obviously was just fine but it was a rough weekend for everyone involved. My parents learned from their mistake and left me for an overnight the first time when I was like 2 months old. I never had an issue being left with anyone else my whole life.

It all depends on you. For me, I would feel comfortable leaving him with my parents who he's spent a lot of time with him at a year.

We've done it a few times. The first time was when she was 1 year. DD was totally fine didn't care that we were gone. We just did it again recently and she did really well but kept asking where we went so that just makes you feel bad!

@Coco Bee: Yeah my mom was really lucky with me and I was a spectacular sleeper from early on. Plus, at the beginning she either left me with her mom or her sisters so none of them minded waking up with me if they had to.