What you want to do, including #2, is duck soup with Garmin's Mapsource program.
I have to emphasize that Garmin's Mapsource is NOT a navigation program.
Garmin's Mapsource program comes with their DVD-based map products. In your case, that would be City Navigator North America. When you install the maps, Mapsource is also installed.
Mapsource has many of the same features as Streets&Trips or Street Atlas for trip planning but it doesn't go nearly as deep as Streets&Trips.
For your route planning, there is a Route tool on the toolbar. You click on it and just start clicking on the map. Click the point where you want to start, then click points along the way for one of your scenic drives and when you've got it covered from end to end, click the end point of the drive, right-click and hit "Cancel" to tell it you're done.
The route you have just created will show up highlighted in a specific colour and will be listed in the "ROUTES" tab. At this point you have a choice how to proceed.
Option A: You can save this "map" with a specific name and reload it later. Then you can start a new one, follow the same procedure as above and save it as a unique name for later loading.
If you follow this course of action, you can later merge the routes into a single "map".
But there's a much better and easier way to do it.
Option B: Save this file so you don't lose your work, but don't start a new one. Just continue with this one. You can start another - different - route, clicking on the different places you want to see. It will show up on the ROUTES tab with a different name.
The ROUTES tab is where you control the display of your routes and also where you can see the summary information for distance and driving time for each route.
You can get all the details, including detailed driving instructions, for each route.
When you click on a route it will be highlighted in a different colour to make it stand out. But you can still see all the routes at the same time.
You can change the display colour for highlighted routes if you wish.
When you have decided where you really want to travel, you can just click on the Route tool again and start clicking to create the final route. When you're happy with it you can print the map and/or the driving directions.
So what's the negative? Well, Mapsource has no concept of "Stops". So when you create a route it will give you the total driving time for that route as if you were going to drive it non-stop. If you want daily driving routes, you need to create seperate routes for each day of driving. It's trivial to do because of the ease of using the routing tool in Mapsource but it's something to be aware of.
If this sounds interesting and you would like to see a screenshot or two, give me a start point, end point and a few points of interest along the way (just city/town names will do) and I'll post a screenshot of what it looks like in Mapsource.
Oh yeah, did I mention that Mapsource is NOT a navigation program?
The best way to use Mapsource is with some other Garmin navigation product, like a Nuvi personal navigation device or Mobile PC on a netbook or laptop or Mobile XT on a PDA or smartphone. Mapsource can transfer your maps and route(s) to any Garmin navigation device for use in autorouting.
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