I have had both and I will say that the Anywhere Map is awesome. It has so much more info than the 295. I purchased the bundle that has the fight planner which gets metars and WX from the internet and downloads that and the plan to the IPAQ. Also, the reminders, flight following, planning, terrain mapping, flight logs and cones of safety are fabulous. I know I sound like a rep for them - *I am not* - but I really like it and the ease (and cost) of updates.