OK - here it is. I did a multi destination itinerary and found my answers! So from the begining - I created a 3 destination itinerary with a few waypoints in between for some traveling today. The first thing I noticed is when I loaded the itineray and the TT displays the waypoints and destinations that I had created, there was a red line after each of the destination points and the next waypoint. So the next step is to start the navigation listed under the option button. This displayed the route only to the first destination. OK so far - so I travel the route indicated to me on the TT. When I get to the first destination the TT says I have reached my destination. OK - so I drive another quarter mile and the TT does not say or indicate anything. So I pull over and have a look - I go to "Itinerary Planning" and it shows the route up to the first red line ( my first destination ) grayed out. I go to options and press the "start navigation" button and low and behold it loads the next segment of my route to the next destination. And there you have it, TT creates segments in the Itinerary for each Destination. You have to tell TT to continue by using the start navigation button in the itinerary's option section. For a bit more info I'm using app 7.481 and na 715.17712. Hope this helps others.