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Take care of any maintenance issues a good month before you go. Tune up, oil change, all those things done and taken care of. Don't change tires the night before you ride off. You don't want any technician induced surprises as you go riding off.
Take some longish rides just to see how they feel. Sitting on the saddle for an hour or two, or three, is not the same as sitting on it all day long. This lets you learn and make any adjustments to you or the bike that are needed.
You will gain an appreciation of the right underpants. If you wear typical tighty-whities, get some bicycle or athletic undies. It makes a *huge* difference to day long riding comfort.
Sunscreen for you, cleaner for the windscreen of the bike. You're in the sun all day long, things get sun burned. Bug splat adds up. An old t-shirt and a bottle of Pledge have been my touring tools for many decades now. Some places require me cleaning almost every fill up in order to see.
Relax, enjoy the ride. You're on a superb bike for this ride. Take your time. Enjoy the sights. Don't get mileage happy, just enjoy yourself. Take breaks. Stretch your legs out, stay fed and hydrated, etc. All of which go to enjoying the ride.
Explore strange sights and interesting roads. Roadsideamerica.com is a great thing for finding weird and obscure sights along the way. That's how I found the Big Mac museum for example.
I think the biggest concerns of most people on a long ride is: how to get the bike home if it fails ya on the road. You probably have towing coverage on your insurance. If your scooter falls apart on the road, i.e. oil comes gushing out of a big hole in the bottom of your motor, use your cell phone to call a wrecker to get you to a u-haul store. You can probably find one within 50 miles of where ya break down, which is how far most towing coverage will pay. Put the bike in a uhaul to get it home. Ya may have to run to a WalMart to get some tie downs for the bike.
For the most part, having a tool pack isn't going to help ya much unless something external to the motor is coming loose. Take a roll of duct tape and a few zip ties in case ya find someone else broke down on the road who knows how to use them. A bottle of water and a snack in case ya break down and get hungry. Rain suit, towel and under armor or Monkey Butt powder. Plan your route, check the weather and make sure ya got ceiling on your CC.
Besides that, have a cell phone and your good.
You will gain an appreciation of the right underpants. If you wear typical tighty-whities, get some bicycle or athletic undies. It makes a *huge* difference to day long riding comfort.
If you are worried about the bike wait till you get a good look at "BIG MAC". The wife and I are riding the new Road Glide Ultra to Blue Ridge Parkway and back. My biggest fear is my wife dozing off behind me, she's done it on my Superglide, oh my!
A three hundred mile ride and your bike broke down?
Curious as to what happened.
Why?
That distance should have been a piece of cake if the bike was in good condition.
You'll be going longer on this trip, make sure the bike will take you safely.
Breaking down can run a ride.
A I bike can break on any trip. Ive seen bikes break down on poker runs. all you can do is keep up on maintenance and make sure you have a back up plan on long trips if it happens. Road side assistance through HOG or other group helps if needed. I just don't worry life is too short so I enjoy the ride
Seams and stitching are placed right under pressure points when you sit on a motorcycle saddle. That 4 way fold where the crotch seam and the elastic leg holes are is the worse. Chaffing and pressure pain from long hours, especially over multiple days, you can rub sores, to the point of bleeding.
Sports shorts don't have any of these seams, so no pressure points. The synthetic wick moisture away well bicycle shorts have special crotch padding to prevent chaffing from pumping pedals while straddling a saddle.
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