Filing a flight plan may look daunting - as do so many things when done for the first time - but has always worked very easy, for me. I would recommend filing through one of the many websites available, then after 15 or 20 minutes call the appropriate service on the phone and ask them if it is all right. I have called some of these services at home and abroad and have only come upon persons that were friendly, able, correct, and very much willing to help.
Remember nothing keeps you from filing a flight plan even when it is not required! Next time you fly cross country, do file a flight plan before, and when contacting FIS add "on a VFR flight plan" to your usual message. Then ask them to activate it, and, above all, make sure it gets closed after you land. At controlled fields this is usually done tacitly but it never hurts to request confirmation. After landing at a non-controlled field, another phone call is the simplest way, and has always worked ok for me.
Last edited by Jan Olieslagers; 15th Sep 2014 at 21:39.