On a Sportster, you can easily run from fill-up to fill-up.
Wear a full face helmet
I learned to wear long sleeve white t-shirts.
Keep a bottle of water at hand somewhere.
I like granola bars to snack on while I ride.

If you attempt an Iron Butt:
Do it while you are fresh.
Leave early,like 5:00-6:00 am.
Fuel stops are the time sink, keep them short.
Don't think of it as 1,000 miles. Just run fuel stop to fuel stop.

 

Ditto, especially clothing and DRINK at every gas up. My son and I did ATL to Boulder in a little less than 3 days out in May, back in June. We went from nice to 40's and torrential rain with 30 mph crosswinds in NM. Coming back in June we hit unexpectedly cold temps in NM again, hail, thunderstorms and then hot as heck toward Nashville. You just never know on a long trip! If you have room for a small travel gas can like the one from Reda, it might be handy, especially crossing Oklahoma and Texas - at least that was our experience - few gas stations on some stretches compared to the east coast.

 

Long sleeve tshirt or mesh jacket, sunscreen, motrin, eyedrops, stay hydrated - not just water, energy snackpacks like trailmix, stop every 100-125 miles and enjoy!

 

Buzzard had some great advice. Your trip sounds like hell to me. I love traveling but would much rather explore than just have to get somewhere. Looks like a mission instead of a relaxing vacation.

 

It may not look cool but with a GPS mounted to the handlebars, you can take some of the smaller roads with confidence. I would also recommend packing some zip lock bags and zip ties. Zip locks are great for emergency waterproofing for your electronics. Zip ties can help with any loose items you discover down the road.

 

I've been riding since 1969, I've ridden in 45 states. The best advice i can give you is not to have your schedule too tight. You will see and experience great things that are not planned. You will want to stop and enjoy places that aren't on your agenda. This has always been my joy in riding. Two years ago riding cross country I used up a half day talking with two 70+ year old retired farmers in Ohio. These guys were really funny, I couldn't tear myself away.

Enjoy the unscheduled along with the scheduled. If your doing motels I tend to get on the road early, I'm ready to stop by 4-5 oclock which makes it easy to get rooms because the cagers usually don't stop until later. Enjoy this one and many more.

PS. Make sure your footwear is waterproof or grease the hell out of your boots, at 60 -70 MPH rain will push it's way through the leather. Wet feet are no fun.

 

I agree with others, nix the cities. Stay off the Interstates, find some scenic routes. You should make a proposed route with google maps, then post it here and ask for opinions. People who know the areas will offer suggestions on how to modify the route to make it better. I've done it that way and got a lot of really great alternatives.

 

X2 on that .. Posted a ride-plan of my upcoming summer trip and asked for suggestions. Got so many good ideas back that it changed my ride plan all around . Now I am as excited about the ride out as the destination , maybe more .

 

 

I went across Canada last year on my super glide. I did a lot of 700 - 800 kms rides before I left to get used to riding long days. I found I didn't need a windshield. Get in good shape, if you can, before you leave. Are you camping, hoteling?