I asked a similar question in general dis. but asking twice never hurts.
I have a wg no bags, how would you do a week long rally like sturgis or daytona? even if I put softbags and a backpack on for the trip I would only be able to carry limited things after my weather gear [coat, gloves, etc] The options Im thinking of are a new bike [ultra] or 6x12 drop door enclosed trailer. My wife suggested i ship my stuff to hotel and ride with bare necessity. Ive never done large rallies and I think its time.

 

between saddlebags and loading up both sides of a sissy bar you should easily be able to carry a weeks worth of stuff.

 

This. Or my dad had a 98 dyna lowrider and had a trailer hitch installed and pulled a small enclosed trailer behind it. Never had any problems. Here's a couple pics of the trailers I'm talking about. My parents have an older one they are trying to sell but I don't think it would be worth coming all the way to Tx for.

http://www.bushtec.com/

 

you can get everything you need in this set up


tbag sissy bar roll $130
leatherpro retro expandable bags $700
sissybar $250

 

add a removable sissy bar & luggage rack. When Im not riding 2 up I put T bag on the passenger pillion and put tent & sleep pad & bed roll on the luggage rack

 

This is how I did it to & from Sturgis, bags are old FLs with easy brackets.

 

I went to Sturgis and thru the Black Hills. It was a 13 day trip. I had Harley saddlebags and a sissy bar Harley bag.

 

I went to Sturgis and thru the Black Hills. It was a 13 day trip. I had Harley saddlebags and a sissy bar Harley bag.

 

I went to Sturgis this year on my dyna saddle bags for leathers and rain suit tbags for cloths and sleeping bag and tent on back of sissybar

 

I went from texas to florida in the 80s on a hardtail springer sportster with a 2.8 gallon tank . back pack and sleeping bag tied to sissy bar