Skippergate, Hi!!
Oh honey you are having a lousy time!
It is a 'mare when you are trying so hard and they just aren't getting it. I'm wondering if Benny's Mumma might be of more help to you as I didn't have an independent sleeper until recently...so I could never just leave him in his bed to sleep until he was asleep. I was his sleep prop and lovie, you see.
I had to stay with him for all of his naps for more months than I dare share with you.
I do have a few ideas though. That first trip out when your LO stayed up for an amazingly long time - they can do that when the surroundings are right. But I'm guessing that you found yourself with a chronically OT baby as a result. Not that day, but the days afterwards. DS could and did stay awake for unfeasible lengths of time at social gatherings...but it often took a week of nightmare 30 & 45 mins naps to get back to normality, hungry when he was meant to be asleep because he would fall asleep when he was feeding because he was OT...and so it goes.
A chronic OT baby is hard work but salvagable. A chronic short napper (a legit one) needs an EASY shaping around their different sleep patterns (i.e. lots of short naps). Benny's Mum is bang on with getting rid of the OT before you try training or increasing. But I see that this is hard when no AP works!
If it were me, I think I'd stay with him to see if I could help him to sleep. Even if it's just sitting next to him, holding his hand or resting your hand on his chest, perhaps gently patting or making a very soft sshh sound. Both ssh patt combined may be too much for him. I'd get some music playing the whole time (soft and in the background...or sounds of the sea or something that he can focus on IYKWIM). I'd stay with or help him to sleep, see how long he sleeps and then try and work to a very rough EASY while you get a feel for what his A and sleep is like. What his real times are etc.
Some babes don't give great cues. Others give misleading ones (my DS's tired cues can often be boredom and need of a change of scene). I work by the clock because for us it is more reliable unless I can see it in his eyes.
Cues can be hard as the sleep window isn't long and if missed, can be really hard to get them to sleep (either crying and hysterical or wide eyed and happy giddy ending in a screamer later on). Spirited types especially need to be heading to bed on the first yawn over those first 6 months. Their window is really short.
Darkness in the room for us has always been key, as has anything stimulating in the room. No toys in bed, no mobiles overhead. Very dark with a nightllight (we recently introduced at night). We have 2 layers of blackout lining. Socks were even stuffed along the top of the window during summer to get rid of any chink of light!
Music or sound in the background helps us.
TBH, I think that in your shoes I'd be tempted to start a post on the naps board afresh. You are worried, frustrated and have a tough LO on your hands (not sleeping in pram, car etc makes it rally hard on you
). A post of your own there will get more eyes on it and hopefully more input from people with more expertise like the moderators and the likes of Anna & Stacey who are amazing with this stuff. What do you think??
I know of a good sleep specialist (my friend used with fast results) but that's in the UK... I know of Dana Obleman in the states who does sleep training with a phone or emasil support package. She's called SleepSense I think. But I haven't used her directly - just bought her guide which helped get us an independent sleeper.
HTH & hugs, together BW will get your LO sleeping
Charlotte