Totaly agree with Eyesurgeon about hours in the saddle and coplexity of the road being more of a factor than miles. When I go to Monterey, it's a 300 mile round trip and the only work I get is a short stretch on Elkhorn Road. It's about the same distance to Murphys, but the roads are a lot more fun....and tiring.
In May, I'll be taking my first long boring ride of about 400 miles, all on freeways, to Vegas, to meet up with my Brother. We plan to stay 2 nights just to rest up for the ride to Fresno then up to Windsor. I have mixed feelings about the Vegas portion of the ride.