Robert
I am planning a similar 5 day trip from San Francisco to Whistler with my 10 year old son (summer of 2008). We were going to go this summer but the wife really wanted me to wait one more year until he was 10 years old. I agreed but get to do the Nelson trip instead (not a bad trade-off). I too worry about all the things that are mentioned above (time in the saddle, boredom, falling asleep etc.). I do plan to have some sort of harness as Twolanerider suggests - i think that is a no brainer. I also plan to keep the riding down to 250 miles per day (thus the reason it will take us 5 days!!) with plenty of stops. We will spend a lot of time stopping and visiting cool places along the West coast and emailing our stories back home at night. We will also camp- out perhaps 2 out of the 5 nights). I will also do a couple weekend rides before this trip to see how well he does.
JeffJ - your idea is a great idea and would take the pressure to grind out lots of miles. I hadn't thought about this but it is worth considering.
either way, its comments like these from MJZ that make you want to find a way to make it work:
"I took my son, who is now 19 and off at U of A, on a trip on my 95 Heritage when he was about 9. The bonding and real quality time spent on that trip was better than all the years of t-ball, baseball, soccer, basketball, swim meets, practices and games combined. To this day we still talk about the long weekend we rode to St. Louis on that bike. We did a couple of cardinal games, zoo, six flags, arch and great junk food. A couple of years ago, he was on a state championship traveling soccer team, on the way back from a tournament in Chicago we stopped at Lamberts Restaurant on I-55. We were all sitting at a big table and my son said "hey Dad, remember when I was a kid we rode the bike up to St. Louis? On the way back we stopped here and ate, didn't we?" Then he proceeded to tell all the cocky 17 & 18 year old team mates how great the trip was. I'm telling you it still brings tears to my eyes.
Anyway Free, having gone down that road words can't express how valuable the experience was. Wouldn't trade it for all the chrome in the world".
Good luck Robert
Free