Should I book a year in advance or last minute?

[User415373]

Hi all,
We're looking to book an all inclusive holiday for next year. DH, ds3 , dd5 and me. We've never been on a holiday like that before (DH and I used to do roadtrips, hostels, self catering off the beaten track type holidays) and it will also be our first time abroad for 8 years (and last for a while!)
I'm finding the pressure of finding something that ticks all our boxes so hard and feel sick at the thought of spending so much money. Anyway my brother has given me a few recommendations as I feel overwhelmed by by the choices and they look great so that's what I'm comparing for now.
I'm looking at June, July or September next year (term time) thinking I'd book now, but comparing the same holiday to this year it seems to be much cheaper this year. For example this one: Hotel
The prices are quite different. But everyone I ask and advice online seems to say that the earlier you can book, the cheaper. So what's your experience and advice for someone as clueless as me? Should we save the money and book closer to the time or book at those prices now?
September this year and next attached for comparison!

If you go next September presumably your eldest will be in Reception and you may get fined for taking him out of school and it may be important for him being in class those first few weeks. Personally I wouldn’t go July, far too hot, we used to go as a family in June, but this was when you were allowed to take them out of school. I always book in advance to get what we want, reasonable daytime flights go quick, know what we have to pay, pay the deposit then save up each month to pay the balance. There doesn’t seem to be any last minute deals anymore unless you can literally go in the next few days and fly unreasonable times.

Thanks @Mindymomo , she's starting reception this year so will be in year 1. I have just quit teaching after over a decade (deputy head of a primary school) which is why we've never been able to afford a 'proper' holiday. So I totally understand the concerns around school but we've decided we're happy to risk the fine.
The price difference above is the same with this June and next June but maybe the price increase just accounts for price rises? I'd be gutted if I booked it and it was £200pp cheaper next year!

Watching with interest!

We have one annual holiday. We've done a good few abroad all inclusive mixed with spells of holidaying in the uk for 3/4 years straight.

With the uk it's always best to book early as it all gets booked so quickly (Dorset) and the prices stay fairly steady.

But with flying out to the sun i also don't know if it's cheaper to book early or not. I could not bare to wait for a very last min booking, but by booking in Feb/March like usual are we paying the maximum ?

Would a travel agent know? Would they be honest if you went in and asked? Or would they befuddle you and just get you to book something?