Been lurking on this thread. OP, I'm soooo different to you.
My DD's first sleepover was at 2 months (it only lasted a couple of hours in fact, but the intention was for her to sleep over at my parent's house). She's stayed there regularly (without her parents) for all her life.
At her primary there were trips in Yr 2 (overnight), Yr 4 (IofW for 5 days) Yr 5 (France for a week) and Yr 6 (South coast for 5 days).
She's also done both brownie and guides camps.
She adored sleepover parties all through primary, and was often upset if it was just a regular party which didn't involve a sleepover.
So, you'll understand, I'm not coming at this from the same viewpoint at you.
Like others, I find it difficult to be anything other than enraged by your comment as very child led family because (a) it comes across as smug, and (b) it implies you care more about your child than other parents. Do you actually think that those who send their kids and don't go and sleep outside the doors of the centre care less about their children than you do?
If my DD was on MN, she would be RAGING at you. She'd be BOMBARDING you with stories of all the fun she's had (sadly, not with me) and telling you just how unfair you are not to be allowing your kid to have the experiences of childhood that were on offer to her.
I cried when she got on the coach in Yr 2 and I cried again in Yr 4; but I didn't let her see this because I recognised the positives in the trip.
She's now nearly 16 and is currently abroad (without parents) on another continent. I miss her desperately, and I keep imagining terrible scenarios (and keep telling myself these are just in my head) but what an amazing experience for her - one that neither of her parents has had. Why would I hold her back from that? She's also (in secondary) been on a German trip, been round Italy (lucky git!) and been skiing in Spain (where she broke a finger!!! Properly injured!).
Oh, and her drama group went to Gibraltar.
All of this without us.
Nowadays, she does all of this without a backward glance. Isn't that fantastic for her?
I once had a parent explain to me that her (youngest) yr 6 child wouldn't be going on the school trip because none of her children had ever spent the night away from home without her. She thought this was an example of her brilliant parenting, and (luckily) mistook my look of horror for awe.
As a PP said, you're raising an independent adult. Yes, (for me) it's fucking horrible. I'd FAR rather DD wanted to spend time with me. But I've always encouraged and enabled her, and she's had AMAZING experiences (some of those just on sleepovers after parties, it's not all about the international travel).
Nearly 16 yr old DD still has photos from IoW Yr 4 trip up on her bedroom wall. That's how good that trip was. And, actually, she wasn't very well that week as she was coming down/developed a cold, and was quite under-the-weather. She's filtered that element out of her memories.
I'm sure not every moment of every trip was all yee-ha and fabulous. And I think a PP was right when they said that schools don't necessarily tell you if your child has homesick moments. But I think it's all part of growing up and (much as I hate it) growing away.
I don't think any of this makes me not child-led. I'm totally PFB about her still. Way more than other parents I know. But I think the difference between you and me is that I'm prepared to see the bigger picture about how expanding her world is amazing for her, even if it means pushing her outside where she wants to be.
Having said that, with trips and sleepovers (because she's so used to them because she's stayed with my parents since she was a dot) I'm NOT pushing her, because she's packed a bag before we've agreed to her going (particularly the Italian trip, which she asked to go on in wk 1 of secondary and it was an extra-curricular club trip for a club she'd joined on a whim)!
But there are other things in her life where she's not so comfortable, but I can see the outcome for her better than she can, so I force persuade her into things she doesn't want to do. Currently she's training to be a referee at a sport she plays. She says she enjoys the training but doesn't want to do it in real-life situations. Meh! Her body-language tells a different story, plus it can give her an income to support the things I know she's going to want to do over the next few years which we can't afford to pay for. I'm ignoring her bleats and sending her out. She's fine.
That doesn't mean I don't 'listen' to her or respect her. It doesn't mean I'm not "child-led". I've got her back if she ever needs me.
But what I think it does mean is that I put my feelings aside for her to thrive. And why would I not want her to thrive? Her world is a bloody lot bigger than the children of that parent who have never slept in a house without their mum.
As previous posters have said, if you don't want your child to go/if he is adamant he doesn't want to, then don't send him. And I think you've made your mind up in any case.
But I think you're fundamentally wrong to hold him back. If you love someone, set them free!