Sounds like a good trip. My gf and I are rolling out that way at the end of June. Heading to MT and Glacier Nat'l park, then to Yellowstone, CO, UT, and where ever else the road takes us. We are still in the planning stages.

 

Our original plan was to take 20 out to Wyoming then run down to Estes Park and run 34 back as they are still mostly 2 lane with a couple of highway stretches in them. Then we decided that all we would be doing is turning out miles and not enjoying the trip, so change of plans we will spend 4 days there 6 days out in Wyoming and Montana and 4 days home.

 

That can be a long, hot run crossing what is mostly "flyover country"!
The last time we did that (2010) we took three bikes on my flatbed trailer and using two drivers, drove straight through from the Detroit area to Billings, MT on I-90.

I wouldn't necessarily recommend the straight through drive with only one driver but trailering is a lot more comfortable and it would give you more time to do much more sight-seeing once you're reached your destination.

I've done my share of riding just to get from point A to point B in my time.
I'm now focused on enjoying my long distance trips and making the most of my wife's vacation time and by trailering and having her fly to a predesignated destination maximizes the scenic riding, especially if she wants to ride solo.

Another plus in trailering is that in case of any problems (mechanical, accidental or medical) getting transportation home is as close as to where you park your car/truck and trailer.

 

I know and I have done that before but now we want to ride out. We are going to ride 2 lane road both out and back. I know there is safety and insurance by trailering, but I'm doing that later this month for bike week in Arizona, This is just something we have both wanted to do for awhile so hopefully it's what we expect or you can be sure the next trip will include a trailer

 

That looks to be the route we are thinking about. We may stay a night in KCMO at her Dad's house and then head out the next morning. We're figuring about 3 days to get out there not being in a hurry.

 

Due to time constraints I too am considering either shipping the bike to Rapid City and both of us flying in then shipping it back when done or putting it on the back of my truck then picking her up at the airport.
Made the ride a few times. It's a long trip from Tampa Bay.

 

That would be a ride probably for later unless you have the time. I have never shipped a bike so do you ship it to a harley dealer? They will hold it for you until you get there and ship it back for you? I'm not sure how prompt the guys are that operate the shipping companies.

 

My father has a Road Glide Ultra, i will talk to him tonight for dinner and ask him about software tips and let you know tomorrow. For our last trip to Nordkapp i remember him loading maps with a pen drive. I suppose the software used to make the maps bits is the same. I'll let you know

 

I'm not sure where I would ship to. Hopefully the dealer or maybe I can find someone that lives nearby. I sent a couple messages to Black Hills HD but have not received a reply.
I've spoke with several transport companies. Most are not interested in shipping to RC unless the rally's going on. I did find a co "Simply Motorcycle Shipping" that said they can do it within 7-10 days to find a driver and make delivery. Price was reasonable considering some of the other quote's I got.

To ride the bike or drive adds 3-4 days one way to my trip or 6-8 days round trip total. We only have 10 days.
Thought about renting but DanG it would cost about $3K. Shipping looks to be half of that.

Will know by end of week if Ma-Ma's time off is approved.

 

Ok, my father said he uses HD original program to creat the maps and export them to the pen drive. But you can use any program that exports gpx files. Once the map is loaded on your bike, you should have a voice in your menu that says preferences, edit, then avoid toll road and he said he flagged dirt roads also. Let me know