While technically missable, (since it is possible to run out of Soul Clusters) this trophy is quite straightforward. It is recommended you upgrade your flying power to get additional flaps and stamina, but it's not necessary if you start high up. There are a lot of places on the map where you can plot out a route to glide through 5 before landing. Just make sure you keep an eye on your stamina while gliding and time your flaps well. I have managed to get upwards of 12 in a row just messing around so it shouldn't be too much of a problem