No mac version.
You can try it free for 14 days.
http://www.microsoft.com/Streets/en-us/default.aspx
Streets can export as gpx files and so gps devices that support gpx files should be able to use route destination and waypoints.
Download the trial and try it before you spend the money if it does not work with your garmin gps.
Be sure to add the megafile poi that was mentioned earlier.
I agree.. The mega file is great. It is what is called a template file... Ending in .stt . You can take and make a map that you use most often save it as an .stt file then load it and modify it for different triips. You can also take the original map and save it so that S&T will load it every time you launch it. You should backup the orginal file
New North American Map.stt before you save the new modfied file. When you go to save the file as a template it will take you to the correct folder. I made a file that had all the profile settings the way I want it and saved it as my New North American Map.stt.
You can make a file that you like, launch the mega file then pick thigs out of it for your trip and paste it into the working file you are making. This is really cool. A lot of things are in this file and we as users can also help make the mega file better by sending information to the persons maintaining the file. There is a campground near me that is not in the database. I am going to give them the name and location so people can find it.
I use S&T to plot out my route and keep a S&T file with every location we have stopped each year by using the stop feature. This told me that we had pulled the BH 9,495.4 miles in 2012.
I also use Basecamp to upload waypoints and routes to my 465t. It is the new software Garmin is developing and many useres do not like it. It is run like a dabase file reather than a simple file app that you safe each route as a seperate file. Basecamp keeps all the waypoints and routes in the same file. There are some good points about this but the biggest problem is that it gets confusing and cluttered when everything is kept in one file/database... But it is free and that is the way they want to program their application program. I am getting use to it & can use it. I just wish they would publish upgrades to Basecamp that were solid with out as many problems.
BC