When to book

[happyplanet]

We have recently got back from our 3rd 'once in a lifetime' holiday. The depression is real! I'm looking to book again for 2021, I'm happy and find it easier to just book everything through a travel agent. We have done villa and also stayed on property with the full ddp the past two visits. For our next trip we were looking at a moderate or value and adding or waiting for free dining to be released. We have a quote from tui for £7100 but this is without food or tickets so seems a little steep compared with our last trip to AKL with DDP and park passes which came in at £8800. I'm a teacher so have to go during school hols and am also toying between Aug/Oct or Xmas 2021.
What I'm interested to know is where, when and how would you book a package holiday, who with and what would you anticipate paying? TIA xx

[Amy1989]

Were also looking at july/august 2021 and no idea when to book either

[Rachv38]

If you want to stay onsite with free dining if offered again then I'd book in April when Disney normally release offer. We've already booked for Aug 2021 although we aren't staying on-site again this time. We've booked 2 weeks at endless summer. Will just book park tickets later on.

[Sew109]

If you book through a travel agent and want scheduled flights don’t even think about booking before the flights are released.

If you book more than 12 months ahead it is unlikely you will be able to get travel insurance to cover you if for whatever reason you can’t go or part of your holiday supplier goes bust.

If it were me and I wanted free dining book the Disney bit when and if the free dining is released as you only pay £50 each deposit and then get the rest when flights are available.