I've travelled extensively around the country (1-bike 48 states, yadda yadda yadda). this past June was the first time I left home for more than a week with a passenger.
Left Saddlebag: tools, extra gear for her - basically, she puts on the gear she will wear on the hottest day, and make sure the gear she needs for cold weather will fit in saddle bag. And her rain gear.
Right saddle bag: tools, extra gear for me - same rules apply - if I'm wearing what I will wear on hottest days, make sure what I need for coldest days will fit. Along with tools and gear, also have Battery Tender and extension cable, 12v air pump, tire plug kit, shock pump, split between two saddlebags.
Tourpak: My luggage (my clothes are bigger): HD Liner bag. I can pack for 2 weeks in just the tourpak.
Tourpak Rack Bag (t-bag on top of tourpak): her luggage - she packs for 5-7 days so we do laundry on the trip. One would think a curling iron and hair straightener will cancel each other out but they do not.
And because she's a girl, and one pair of "shoes" won't do, extra riding boots for her are in my luggage.
yes, I throw clothes away to lighten the load and make room as trip progresses.

Rule of thumb, when on the road, should only have to get into the saddlebags. Also make sure snacks are packed on top in the saddlebags (beef jerky, apples, bananas).

also manage to fit the bike cover in one of the saddlebags (exigent packs small) and my laptop in the tourpak.

The beauty of this - when she wants to go shopping someplace - "sorry dear, no room"

 

Well said.

 

The adage about twice the cash and half the clothes is incredibly accurate, same as the advice about sending home stuff along the way. It is amazing how many days in a row you can wear the same jeans :-)

Only thing i can add is to ensure as much heavy stuff gets as low as possible. Roll up everything, waste no space-socks inside spare shoes etc. put your rain gear on TOP of the stuff in the tour pack. Go to a bicycle store, buy some padded shorts, good for an extra 100-20 miles a day easy. Wash them at night, hang over hotel heater-presto, dry in am. Have good map, or gps and if you at least make it to South Dakota, may as well go across Montana dn do the Beartooth, you owe that to yourself.

 

FWIW I wear my jeans 2-3 days all the time before washing. Never could understand why ppl don't do that they last a lot longer that way.

 

I pack the tools I take and the tire repair kit and small compressor in the glove boxes of the lowers. All rain gear in the right saddle bag along with the wife's extra shoes, snacks and cell phones. Left saddle bag holds the cover, some cleaning supplies, a roll of toilet paper my extra shoes and the heated jacket liners. Then her clothes in the bag on rack and mine inside the tour pack along with an iPad, binoculars and camera. We normally go 4 days then do laundry and start over again. Depending on where we are going and what time of year the heated liners may stay home. Biggest problem I have is getting the wife to pack in layers and not outfits, I allow her the largest bag and tell her it can't weigh more than 20#s. Money, credit card, insurance card, triple A card, wallet and a pocket knife in the windshield pouch. Don't like sitting on anything or anything in my pockets on a long ride. Fairing mounted GPS on the left and a drink holder on the right, being able to have a drink of water while you are moving is a hell of a lot better than having to stop just to get a drink. And as others have mentioned try some riding shorts for the long days they do make a difference, I wear the LD comfort on the long days. Have fun, we are already planning next years ride form SE Pa. Through ND into Mt, Id, Wy and back through SD.

 

Here's checklist I've used in past we primarily camped but credit card camp list link too.

http://micapeak.com/checklists/mclist.html

 

Beartooth Pass! My favorite!!! (I've been all over Colorado, Wyoming, Yellowstone and the Smoky's in TN & NC, not to mention right here at home, so FWIW, my advice is to do Beartooth Pass at least once in your life time!)