When do they start discounting holidays?

[Jer_1974]

I have a few weeks off and want a bit summer sun. Thomas cook have deals leaving on boxing day from Glasgow. But at nearly £2k for a week all inclusive is a bit more than I want to spend. It's showing 17 holidays and I have checked over the last few days but they don't seem to be coming down in price. Do I wait till boxing day to book and what's the chances of getting it cheaper the later I book it?

[BigAlinEmbra]

Virgin holidays are advertising their sale on here now.
I had a quick squiz for April and Barbados was starting about £650, albeit some of the places looked a wee bit low rent. Nice hotel in Cuba for a fortnight will set you back about a grand.

Wouldn't go in what we consider "summer" though, as you're edging into hurricane season.