Eylon: I've been planning my first trip on the "mother road" & am willing to share what I've learned so far....1. LENGTH of the trip is up to YOU. It could take 4 days to 2 weeks or longer. It depends on how much you want to see on this trip. Don't expect to travel any faster than 50 mph average each day due to the stops. From what I understand, you'll probably not see everything in one trip anyway. 2. WHEN to travel depends also on you. I choose mid September due to less rain & lower temps. 3. I bought the BOOK: "Route 66 Adventure Handbook" by Drew Knowles to determine which attractions I'd like to include on my trip. It is very helpful. Good luck on your trip. I hope this helped you a little. Bob W.