Is there a program that allows you to plug in a couple of destinations and it makes the fastest route to get to each of the destinations

Microsoft street and trips

I used it ( with updates) for over 6 years routing several trucks doing 4 to 10 stops a day.

There are many others, I do like it becuae it is so easy to use. And it seldom sent me down one way streets, and on roads that were not there.

Use Google Maps almost weekly to plan complete driving trips. Point to point. Free!

Google Maps (http://maps.google.com/maps?hl=en&tab=wl)

Thanks but are there any free ones? And I couldn't figure out how to do it on Google maps

The one I use only costs 40 dollars or less, and it will allow you to put in dozens of stops and figures the best way to do them, or you can put in whichone has to be done in which order.
It allows you to put in how long you plan to be at each stop ( est layover) and will even allow for over night stops,

If you are doing a lot of routing for several stops it is great,