I don't know the answer to your question, but if I want to go away at a specific time, then when I see a price that I'm happy with, then I book. If it comes down in price at a later date - then so be it. I was happy at the time of booking.

I find the prices are lower over the Christmas and New year.
Last year I booked a holiday to Egypt after seeing it on Thomas Cooks website for half the brochure price.
This was mid November to depart 3rd December.This is not a popular time for holidays as people are normally think about Christmas.
I am hoping the same offer will be available this year bit I am prepared to pay the current web price because the hotel was excellent.
I will also be keeping an eye on the prices for next May just after New Year.
I always manage to get the web price from the Travel agents and sometimes they even discount the price even more.

As a child in UK I always recall that tour operators started their holiday campaigns over the Christmas holidays on TV.

Generally, when the tour op releases their first brochure for the coming season they will put their main hotel allocations in that brochure as they are the rooms they will have lots of or block booked and paid for, for the whole of the season. They also add the more popular accommodations.

Other accommodations tend to come out in the 2nd or subsequent edition brochures.

But, if you book independently you may often find that flights are cheaper up to 350 days in advance (take into consideration your return flight date for the 350 day count). We always book independently now we live in Cyprus as we're not too happy with the travel agent fees here.

We book the flights first as that's the most important part to plan the holiday around. I then search for the best deals on accommodations in the area we want to be located and find there is definitely a fluctuation. So I search before I book flights and for a couple of months afterwards to keep an eye on trends. You will find that prices will go up as a rule from Friday to Monday as most people look for holidays over the weekend. They may make their decision and phone to book on the Monday if they don't do it on the actual weekend. Prices then often drop midweek.

I do the same for my parents. Their bank gives them insurance as long as they use their credit card to pay for all the parts of the holiday and they have had to make a claim once due to my dad having to go in hospital a couple of days before their departure.

Shell
Limassol, Cyprus

I've looked at DIY and it works out far more expensive. Kept my eye on prices on a weekly basis and they haven't dropped, in fact they've gone up!
The hotels I am considering to holiday at are not showing on any of the tour operator sites yet when I Google the hotels the they are listed under these tour operators.
What is going on ??

I've looked at DIY and it works out far more expensive. Kept my eye on prices on a weekly basis and they haven't dropped, in fact they've gone up!

I think that this depends an awful lot on where you want to go. We go regularly to one of the smaller Canary Islands - none of the big TOs offer packages to La Gomera, only a couple of smaller specialist operators that put together their own bespoke packages and I can put my own together for far less by dealing direct with a local agent and booking low-cost flights to Tenerife as early as I can. Such flights do increase in price rather than drop the nearer you get to departure date - that's their pricing model. On the whole I don't want to go to the places that the big TOs go to in the Canaries and especially not what is likely to be on offer at a discounted rate nearer the time to departure.

I have thought that perhaps we should take the chance and look for a bargain late offer to Tenerife and just use the flights rather than stay in the accommodation included because sometimes the big TOs are doing last minute package offers that are very cheap but each time I've decided not to take the risk that I won't be able to book us into the apartments we particulary like. So for La Gomera we always do DIY and book up as early as we can.

On the other hand, I've never gone DIY to Tunisia because it was a good bolthole for a bit of winter sun at short notice and it was always possible to get a good deal for a standard TO package at relatively short notice if all I wanted was a reasonable hotel for a week's chill-out doing not much more than lazing arouns reading and wandering around the souks and medinas.

And a different scenario again is when I go to Cuba - I probably could do a DIY there cheaper than what I pay a specialist dance holiday company. But then I wouldn't get the service that I get from this small specialist operator whether I travel as part of one of their groups or on a bespoke package tailored exactly to my individual needs. So, yes, it is more expensive than a trip to Cuba needs to be but I do think that it's good value for money and that's always the most important thing to me but what constitutes 'good value' depends a lot on what you are looking for. A very cheap mass market package to a large resort in the Canaries wouldn't be good value to me at almost any price whereas an expensive specialist dance holiday to Cuba is.

In the end, the best time of year for lowest prices with a tour operator is whenever and to wherever they are finding it hard to shift holidays and that can be quite unpredictable!

SM