There are lots of nice places to take the day off all along the Transam, but if I had to pick a place for family to fly into, it would be Missoula Montana. Very nice town to see, have french toast at the Raven Cafe on E Broadway, rent a car and drive to Glacier National park. That would be my pick.
Don't leave out rest days on any tour this long, or if you feel that you just have to keep on moving (that happens on tour for some reason) do short, 20/30 miles days once or twice a week.