I did the Saddle Sore 1500 last year on an 07 Ultra, 1601 miles in about 29 hours. Freeze 6 or 7 bottles of water and pack then in a cheap cooler, they'll thaw out but will help keep them all cold. Also get a small can of baby powder and use it whenever you stop for a potty break, your area below the waist will thank you for it when you get to the end of your trip.
Lastly, keep good documentation and fuel recipes, the fee for the certificate is pretty high.
Matt,
Good luck on your adventure. I did across country from Boston to Oregon on US highway 20 in 1959 on my 48 Harley. It took me a little over 5 days. I finished my 49 Pan a few years back and planned to do the same trip. Still planning, but recent events and your blog have made me aware this is something I need to do. Hope all goes well for you and remember when it stops leaking oil it's out of oil.
Sounds like an adventure. I might recommmend a Camelback for fluids. That way you can keep both hands where they belong, and it's easier than trying to open and close a bottle. Plus you won't need a cup holder. I can't wait to get home and throw a leg over my bikes. Good luck!
Thought I should say hi to everyone and thank you for you support I am so excited for this trip!! Thanks to Matt I will never forget this summer. This will be my longest ride as a passenger so be expecting lots of blog updates I think I may get bored.... I don't think that Matt has much to worry about with being comfortable I am going to try to give him the longest back rub he's ever had in return for this amazing opportunity!
Have a GREAT Day everyone