Hi, my daughter had just turned 3 when we started her in the trailer. We took her out as each day for two weeks building up to fifty kms. But we gave her things to do, such as a treasure box of nibbles (all her favourite foods), her favourite toy, some colouring in paper and a book.
She did moan a little but soon she just got into the swing of it all. As she had everything at her finger tips she didn't need us to stop and give her things.
In the mornings, my husband would get things organised ie pack up the tent, while I made sandwiches for breakfast, we would then eat as we finished packing. My daughter ate her breakfast in the buggy and then we would set off. We tried to leave the camp as close to 7 as possible. Its cooler to ride and it meant that we could cover as much ground as possible before the roads were busy.
Most days after Em had her breakfast in the buggy she would have a little sleep. Then it would be a morning tea stop, and quick run around, and then we would head off again.
As the previous person said, the gear bags were always available and we would be all set up and ready to play.
It isn't easy but this worked for us, I know others who did it the complete opposite and were last to leave and last to arrive and this worked for them. I'm one of those people who likes to explore the places we go to so prefer to get there as quick as possible. I also like to get Em settled quickly and tire her out.
One of the other things we did was to hire one of BV tents, this didn't suit us very much as the tents were always near the kitchen area and were very noisy but it is an option.
Good luck, if I had my time again, I would def do it with a tandem and buggy as then you are all together. We took turns with the buggy which was good and bad.