Itinerary planning in general on the TomTom
Not easy. Best to go to Costco and pay 23 bucks or Best Buy and pay 40 and buy Microsoft Strees & Trips. You can pay more and get a gps with it for use with a laptop.
Create Push Pins for all the places you want to go on your route and name them 01 blah blah, 02 blah blah. The use a free download (actually they would like, and deserve, a donation) GPSBabelGUI. It will come zipped with some files you don't need. The file does not install, but executes, so unzip them to your desktop and delete all but GPSBabelGUI.exe. With that, you can do two things, one translate the MS S&T file to a TomTom ITN file, and, if you wish, you can make POIs out of the waypoints. Advantage being, the TomTom can warn you when you are getting close to one, if you turn that setting on in the TomTom. But, you must also create a graphic for the POI file. That is no issue. MS Paint is in the Accessories area on your PC. Do a Image/Attributes and change it to 22 by 22 Pixels. Then do Image and make sure Image Opaque is Checked. Then use the "A" on the side panel to put initials inside the box. Or you can get creative and make a drawing you like, to represent the POIs in the group.
Name the ITN file and the POI file and the Graphic file the same (the extensions will be different). Copy the ITN file into the ITN directory and the POI and Graphic into the Maps Directory "United_States-Map". The POI file will have a OV2 extension, the graphic a BMP extension and the Itinerary a ITN extension.
The reason I name the points with numbers first, is so if the TomTom is smarter than me and wants to rearrange the waypoints, I can put them back the way I had them once they are in the TomTom.
An important thing to note is that TomTom (and Garmin??) want Longitude before Latitude (go figure), so open the ITN file with Notepad and inspect it. It should look like this.
-108.22222|37.22222|01 blah blah |0|
-108.22225|37.22225|02 blah blah |0|
etc.
What are those vertical lines, you say? They are pipes. What's a pipe? it is the vertical double dash just above the enter key on most computers.
The last digit represents what the Point is, Start, End or waypoint. Zeros are Waypoints. I am not sure about 2, 3, and 4.
When the file is converted, everything is a Zero. When you Load the Itinerary, it says the last point is a Waypoint, Change it to a Destination? Say Yes, and it will change the number for you. It expects you to be at the starting point already, but you can tell it to navigate there where you are, or you can say HOME if you are inside a building where it can't get a signal.
Another anomoly. If you are on an overnight trip, you MAY have to click through all the points you have already visited, and say Show Visited or something, else, it may want you to start at the beginning of the route.
Now, what if you want to use the same route to come back? You can re-order the trip by numbers in reverse in the TomTom, or, you can download a free software that will do that for you and save it under Reverted blah blah. Check the web, it works.
If I remember right, you won't be able to read the POI file, but you can create your own in Excel Lon/Lat/Name. Save it as a CSV or Tab Delimted file, and use your new best friend -- GPSBabelGUI -- to change it to a POI file (OV2).
Now, there are many sites, like POI-factory.com that have downloadable POI files. They are in any number of formats, but your new best friend can help you translate them to TomTom format.
One good way to find new things to see on a trip you already are going to take, is look at it on Google Earth. Click on things along your route, and if you see one that appeals to you, pop it into an Excel file. Bear in mind, these folks that post on Google are not in the woods when they do this, so their accuracy may be lacking, but if you can get in the neighborhood, you can ask somone. Be thankful that you can find new things this way, and try to verify it before leaving, if you can. Same with stuff you download. Things change places close/move.
Enjoy.