I use FlightStar and JeppView to plan my trips. The software is easy to learn, although there are some power user features that take more time and parts of the interface are idiosyncratic. With the optional weather downloads and JeppView software, you can set up an aircraft, plan a route and print out a complete trip kit with approach plates, enroute charts and pilot log.
It can display Jeppesen-style VFR charts and airways. You can also view VFR plates for airports and IFR approach plates. These charts are updated automatically over the internet. It’s powerful stuff and good enough for a corporate flight department. The only downside is the price. For the IFR version with European charts, it costs me around €1700 a year.
Cheaper (possibly free) alternatives include Autoplan IFR for planning airways trips and Tony Griffiths’s Cross-wind, which is a comprehensive VFR flight planning program.