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Mapping tool for multi-mode, multi-destination trip?

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I'm trying to find a program that will let me plot out, and eventually print, a map of upcoming trips. I've looked at a number, and each has a problem, the most common ones being limited number of destinations, and no ability to make one stretch off the route car/rail and another by air.

For example, I will be arriving in Rome, flying to Palermo, driving around Sicily, taking a train to Naples and then flying to Nürnberg, and continuing onward with more stops. Obviously, Rome to Palermo and Naples to Nürnberg looks a lot different by air than by road!

So, if you know of any, or have any ways of adapting any, I'd love to know. I'll be on the road for a month, with quite a few stops, and traveling by air, rail, train and river cruise.

Thanks for any help!