Leave your long lenses at home unless you’re going up in an aeroplane of some kind, reason being is that the wind can really play a big part in keeping your camera stable or there lack of in a helicopter as your lens will have to fight with downward force as well as from the front of the aircraft. Taking a 24mm or 15-30mm is best when flying under 2,000ft. Anything up to 70mm is great, however the wider the better is normally the rule of thumb here and take some high quality fast glass such as f 2.8 or anything that bests it. If you are going on a high altitude flight then 85mm at most works best in a helicopter.
Take two cameras with a lens attached each. My preference is a wide zoom and a prime, if your pilot / tour company allows it, place an action cam of some sort securely inside and record your shoot. This is a great way of seeing what you did right and wrong, give commentary while you shoot too if necessary. It’s a nice way to improve and build your skills and of course shots you may have missed.
Wear something to cover the eyes like skydiving goggles or a strap to keep your glasses on if you wear them assuming you’re up in a helicopter. The wind has ripped glasses off my face before which made for a tricky drive home so take a precaution if you are flying doors off in either mode of transport but mostly with helicopter and microlite or ultra light aircraft.
If you are planning to go up into an ultralight aircraft, take something to protect your legs from the wind, they will get battered around somewhat and often new flyers will instantly regret not having insulated their legs and arms. It doesn’t really matter the time of year, its going to be much cooler than on the ground so grab some leg coverings such as ski salopettes which cost around $100 USD from any local distributor.
Here are some very important tips for shooting from a plane such as the cessna that should always be adhered to. Other items to check on fly day are the color of the seats inside the plane and your choice of clothes. Always wear black, everything from your toe to nose should be covered including wearing a balaclava if possible and your kit bag should also be black, if it has some reflective tabs then cover them with black duck tape. Since most planes will have you shooting through glass the reflection will occur at some point, the only way to reduce it to almost zero is covering yourself and the seat of the plane black. Easy way to cover the seats in the back of a cessna is using a mat black (no shine, polyester) untapered bed sheet for a twin bed, that is normally big enough to cover up those rear seats.
Make sure the windows are not only completely smudge free (take some window cleaner of your own and a lint free cloth just in case) but also single ply glass. Dual pane or dual ply like the kind you get on commercial jet liners can create so much shadow and reflection that your black covering will be next to useless as one pane of glass reflects off the other and bang goes your shoot.