You should be ok with that lens. I took a Sigma 28-200 on a Nikon D50. A 500mm lens would be a nightmare to keep steady. Most of my shots were below 100mm. The following images I took are not brilliant but they weren't the main shots I was after so didnt take enough to get the best available ones.
There are a few things that will be against you here, depending on the aircraft and its condition.
1. Aircraft / engine Vibration. A VR lens would be great here, or a fast lens. Take loads of shots and you should get a few relatively vibration free.
2. Many small aircraft will probably have perspex or similar side windows. They get scratched and cloudy ( and dirty) Clean them all first, inside and out, but carefully as they mark easily. Or, open the window and lean out. Interesting if you are banking sharply!
3. Turbulance. There is a lot of air turbulance especially close to the shore if there are any cliffs or buildings.
4. Time of day. Check the buildings will not be in shadow. ( time of day and tides affect turbulance too )
5. Get as low as you can. We were critisised for going down to 28ft above the sea to get a shot of a vessel. We both survived, so it wasn't that bad!
So heres a few that I took. Of course I was in the passenger seat!
Margate Lifeboat Station
Margate Coastguard Station.
HM Coastguard, Deal Sector Base ( my office at the time)
As you can see, they are not the sharpest due to the vibrations and I had to enhance them because the side windows were pretty dirty, scratched and cloudy.
Good luck with your shoot. You could always practice from the passenger seat of a moving car to get a feel for how the lens performs in a moving shaky environment!
Allan