We're going through this right now. DD has been trying to drop one of her day sleeps for a few weeks but silly Mummy has only recently figured it out. The first thing I noticed was that her afternoon sleep started getting shorter and she started playing for longer in her cot when we put her down before having a sleep. Then the morning sleep was pushed back half an hour too. Meanwhile I just kept to the same old routine and because she didn't fight it, I didn't realise. Then she suddenly stopped sleeping in the arvies and would just play in her cot for 45mins - 1 hour and then crack it to be gotten up. And the main trigger - she was totally fine despite the lack of sleep.
Mj has been trying to drop her sleep for a while now...
We take it as it comes each day, honestly i was thinking about leaving it about a year ago, so we decided that she would have 'quiet time' on her bed, curtains drawn etc, we would have a story and i would put on a CD and told her she could come out when it was finished (it ran for about a hour) and that she didnt have to sleep.
this went on for a week and then she started sleeping again... its has been on and off since. If we have things on, she always misses the sleep, but generally i try and get her to sleep every second day. She didnt sleep Friday, Saturday or Sunday and SOOOOOOOOO needed it today, she was at CC today and i spoke to her careers as she normally doesnt sleep there and they offered to sit with her to help her sleep, which she did.
She is almost 3 and 1/2, Im not sure how long she will still need them several times a week, but she doesnt need them each day now if that makes sense.
I encourage my DS2 to 'have a little rest' (if I say it's time for a sleep he will just fight me saying NO!) just on the couch and he sometimes nods off and sometimes doesn't.
I also found that they got to a certain point where if they had a nap they were later/more difficult getting to bed and it wasn't worth the 30 min to and hr I got of peace in the arvo. I think you kind of have to play it by ear and if they look/act like they need a sleep then encourage it, but if they are fine without it then just leave them. A bit of a guessing game, like a lot of parenting!
For us it was when after having her day sleep, DD would be up bouncing off the walls till all hours of the night She was happy enough to have the "hours quiet time" and would often nod off, but then getting her to bed at night became really hard, where skipping the day sleep yes she was a little ratty towards the end of the day but she'd conk out like a light come bedtime. Big difference
I'm not sure it's as cut and dry as no sleeps ever. DD hasn't had a day sleep routine for four months, but she still sleeps in the pram or car if tired but not everyday.
I find the days she sleeps in the day are longer because then she's up till late and takes ages to fall asleep.
I would think it's a long transition process and they stop sleeping in the day when they stop falling asleep at random in the car or pram etc which will probably be a long time for us yet.
When it started to impact night time sleeping. The time is coming for us to cut day sleeps *sobsob*. My kids are waking anywhere between 4.45am and 5.30am. Just rediculous....but I love the time they sleep in the day it's my only quiet time, I am soooo reluctant to say goodbye to it!
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She was happy enough to have the "hours quiet time" and would often nod off, but then getting her to bed at night became really hard, where skipping the day sleep yes she was a little ratty towards the end of the day but she'd conk out like a light come bedtime. Big difference 
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