For me it's all in the planning so that everything goes smoothly from the minute we get to the airport until the end, with no surprises where I can help it. I do a lot of research, checking on tripadvisor and other sites, and all the major travel companies to make sure i get the best holiday for my family.
I also get a lot of anxiety when booking a holiday - I tend to be the person doing the research and I am always conscious that I need to cater for the needs of the whole family - I feel very responsible for their happiness on holiday. That said, it also has to be a fine balance, I've got to enjoy it just as much as the children do!
I'm fairly fussy about where we go - I want the ease of a package holiday without the resort feeling too touristy (yes I am a nightmare!). But it has to be near a beach and also within walking distance to good restaurants. I want lots and lots of photos of the room, the hotel and the wider resort (and a map!) so I can see exactly what I'm getting.
In terms of accommodation, My boys are now getting older, one has just become a teenager, so I don't want to share a room with them, we all need our own space, but within the same apartment, we are not quite ready yet for them to have a different room in a hotel for example, unless it had a connecting door. Most sites don't give you this - might offer 2 twin rooms for example, which I dont feel comfortable with.
We need a decent amount of kgs for our luggage, jet2 were brilliant last year with 22kgs each for a week (which was actually way too much for us), so I've got to admit that this year's holiday with tui has come as a bit of a shock with only 15Kg each for a two week holiday (which will be tight). It would be brilliant if travel companies could bear in mind the duration of the holiday when allocating baggage allowance.
We've recently tried all inclusive holidays for the first time, our children love them. I prefer options where there are different restaurants you can use, otherwise the hotel food can be a bit samey.
A pool is a must for my family, as is the sea. Also hotels / resorts with other activities - tennis courts etc where the kids can entertain themselves without my input, it gives them just enough indepedence and allows me some time on a sunbed with a gin and tonic.
On flights my boys can entertain themselves these days, we take the iPad with films on it and games. They also enjoy an inflight meal, when it comes to travelling we relax all usual rules in order to make the best of it (my youngest was tucking into chicken tikka masala at 7am on our holiday in October, not my choice but it kept him happy!).
Best piece of advice for travelling for the first time with babies? They have babies in Spain / Greece / Italy too... you really don't need to pack 3 boxes of formula or enough nappies for two weeks!! (yes I did that).