Current TomToms and itinerary planning feature

How many stops do you need on your itinerary, and are you willing to call them up manually in sequence as needed, or do you need them to come up automatically one after the other?

 

Several of the new models are capable of managing it - but in a different way than before.
You could plan a route to the end, then add another 9 intermediate stops. This can be planned on the device, but the web site provided makes it a good bit easier. The device will then use traffic and average speed information to pick the best routing between each of those stops. You can also save routes of that sort both on the device and out to the web.
It's not quite like the old itinerary file method, but it works.

There's another way to force a very specific route (it won't try to deviate at all, bypassing the routing engine and ignoring any traffic situations) by saving a specific flavor of *.gpx file to the web and letting it propagate to the device. Not always practical, but very deterministic.

What other features are important to you?

 

I might be able to clarify a couple of things by using some analogies if you are already familiar with the 3 basic flavors of *.gpx files.

 

Have a look if that tell you anything.

http://download.tomtom.com/open/manuals/GO_Basic/html/en-us/MyRoutes.htm

 

Rather than itineraries, they talk about routes and stops these days. ONLY the motorcycle editions still specifically support the old style *.itn files. Why? I have no idea. It's only a simple difference in firmware, which is what makes the absence on other units especially annoying.
My personal favorite of the moment (at least of anything widely available to the public - the 'fleet' hardware is scarce and expensive!) is the GO 620.