Hi Bob,
I've put up a facility for exactly this type of thing over at Segway Central:
www.segwaycentral.net/gliding/glide-routes
There's only a couple of test routes uploaded for now but you should be able to get the idea.
Currently routes can be uploaded as GPX or KML files (many smartphone apps can create these using the in-built GPS). A newer version of the software I'm using should allow the drawing of routes directly onto a map but I don't have a release date for this yet.
Please feel free to have a play with the site and let me have your feedback as to what could be improved.
Re the database of glide-friendly places, I do have a fledgling database option for this on the site but its hidden from view right now as I haven't gotten around to finishing it yet. If people here can give me an idea of what they would like it to contain I'd be happy to spend some time putting it together for everyone to post their own entries.
I also have a half-written article on the legal status of segways around the world and need to find some time to finish it off. It's intended to be a work in progress with updates made as and when they are known. If that really is of use and people can furnish me with the necessary information then I'd be happy to put it all together and keep it as up to date as I can.
Regards,
Paul