We took our soon to Maui when he was 8 months and HK at 11 months.
He slept at least half the time if not more.
Otherwise I didn't find anything extra was needed that I didn't already do when we are out and about in town.
1. Ensure you have some sort of entertainment you know they can focus on for a while. With my son he had no problem sitting still for 30-60 minutes watching a show on the iPad. Or maybe toys you know they like to play with to occupy their time when they are awake. We had some toys, kids apps and some shows on an iPad that we knew could keep him occupied.
2. Obviously the given is get them up and out of the seat once in a while when not sleeping. Walk them up and down the aisle and what not.
3. Snacks - We brought milk and a bunch of his favourite snacks in case he gets hungry. When we went through security with the liquid all we had to do was put it in a plastic bag and they do a special swab test on it. You are allowed to take drinks more than 100ml for babies. If he is still only breastfeeding I guess this won't be an issue anyways.
4. If your kid doesn't fall asleep on planes you can give him children's gravol. Since he is 5 months I would cut a tablet in half and dissolve it in his milk. It will help them sleep.
5. When to get on really depends on your kid. If they are ok with sitting still or can be occupied easily getting on first is nice so you can make sure you have room for all your gear in the overhead bins. We always got off last. Much easier and your stroller will be there waiting for you as you exit the plane.
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