I'm not sure exactly when we started either, or how I knew the time was right, but gradually Theo started to become more interested in the act of going to the toilet. I would say that I was just going to the toilet and he would come along with me...always nice to have an audience. He knew where his poo and wee came from too, so one day I bought him a little Thomas toilet seat, and began letting him sit on it and asking him if he needed to go for a wee. We just started doing this in the evening before he had a bath, then gradually added morning nappy off time too. So it carried on this way for a while, just gradually easing in and getting him aware of where you go to the toilet and how it feels to do it not in the nappy.
I haven't read up on many tips on how to do it, but just went on advice and our own instincts. It's just gone along at it's own pace and I never thought, right we need to crack this in 3 days sort of thing, but we've still made progress.
Gradually we extended the nappy off time, and have spent longer periods of time at home so we can make the most of getting used to it. I would ask him if he needed to go, and I'd sit him on the toilet and have a go, sometimes he went, sometimes he didn't. We used stickers every time he went, which he loved choosing. He then started asking for the toilet of his own accord, so we'd race upstairs to have a go. At this point he still wasn't using the potty and preferred the proper toilet, and he wasn't wearing pants. It took a little while to introduce wearing something on his bottom half and him knowing that it wasn't a nappy, which is something we're still working on too.
When we got back from holiday a few weeks ago now (sniff) I decided that we would take a little more control of the training, and try and do whole days of no nappy's and wearing pants. We went and chose some new pants for him (Thomas obvs) and tried to explain that they were not a nappy and that Thomas didn't like it if he got wet! So since then we've been trying to keep the pants on most of the time, but he does like to be naked a lot of the time too.
He's started to use the potty, and quite a lot of the time on his own without asking, which is great. We've had quite a few accidents, but they're definitely getting few and far between. So that's at home nearly covered.
I decided to just bite the bullet and go out with him just wearing pants, we had a short journey in the car and a morning at the zoo with no accidents on our first nappy free outing. I bought a travel potty/toilet seat that works really well for being out and about. Before we left the house we made sure we tried to go, then once we arrived we made a trip to the toilet before going in. Then half way round I asked him again, but he said he was fine, we then passed some toilets and we made sure we had another try just in case. He went both times which was great, and we had no accidents whilst we were there. We met up with friends for a picnic, and I guess because he was excited and distracted by his friends being there, and not having a proper toilet he had two accidents. Then he got stung by a bee, so after this I called it a day and put a nappy back on him (plus I'd run out of pants and changes of clothes!) But it didn't deter us, that was our first proper day out, and a morning success is good enough for us. The rest of the week we stayed fairly close to home, just trying to get used to pants and potty!
We visited my Dad at the weekend, and Theo was excited to show off that he could go to the toilet like a big boy, which helped a lot! On Saturday we went to the seaside, and apart from wearing a nappy for the hours journey (no-one wants a wee sodden car seat to sit in the sun for 8 hours now do they...) he stayed dry all day long. We visited my uncle, and he went to the toilet there with no problems, he didn't necessarily ask to go himself, but he went when we made him try more often than not. We used various public toilets, all with no problem! We were out from around 12pm - 9pm with no accidents at all, winner! The next day didn't go so well, we took his potty with us, which we kept asking him to use if he needed to. We managed to catch a few, very nearly missing a number two, and then had one or two wee accidents, but I put this down to over-excitedness, tiredness and forgetting on our part.
We're back to normal again today, staying at home all day to recover from the weekend, so it's been spent naked or in pants, using the potty on his own and asking for the upstairs toilet and no accidents! We're still using a nappy for nap time, but it comes off straight away when he wakes up but I have noticed that it seems pretty dry anyway, so perhaps that's our next step!
So we've had a couple of completely dry days, using the big toilet and potty for both 1& 2's, asking for the toilet, using the potty without being asked, wearing pants, pulling down pants, using potty in public and using public toilets! So it's safe to say we're making progress, and hopefully it won't be too long until we're completely accident free! There's no turning back now....