If your starting a company would definitely take a look at Edelweiss Bike Travel. They are a worldwide company and have their stuff together for sure.
Most of their "tours" seem to be a lot more adventure rider than Harley. As a matter of fact I don't think they even have any harley's or cruisers in their fleet. They have on and off road semi-guided tours, some with all hotel stays and some with camping arranged.
My whole family rented 1200RTs from them when we traveled to Scotland. You do have to sign up for a "tour". It's not just a show up and rent a bike type of thing. The whole purpose of the trip for us was to tour the country on bikes as a family. My mom rode with dad and my sister with me. They helped arrange anything we wanted and delivered the bikes to the hotel at the start of the tour. There was a group of people all there for this tour about 8 or 10 maybe) and they had a briefing every morning with breakfast supplied and they told you where the day would end and where there would be a lunch stop. Lunch stop was optional if you went somewhere else. They had hand marked maps, tips and directions for anyone that wanted them. There were spare bikes and support trucks that carried the bulk of your luggage every day. If you wanted to ride with a guide and the group you could. We rode by ourselves a lot and explored a little more. As long as you were at the hotel (that was already booked and paid for) that night and they knew you (and the bike) were alive that's all that seemed to matter. It was a blast and I never got that Cruise ship type strict time regimen feeling. And Scotland. WOW. soooo beautiful. We were lucky enough to have 10 days of good weather. IN SCOTLAND!? We only got rained on a total of maybe 2 or 3 hours the whole time.
Yes it was expensive, but they have figured out their demographic and supply a WHOLE lot of value for the money. We had home (or road)- cooked meals that the guides cooked, they were knowledgeable (and ready) about how to fix any issues we had on the bikes and they would buy you drinks at night at the hotel bar
: and come for your bags in the morning at your room door. It really was a trip of a lifetime and I will be doing it again with my girlfriend at some point.
They have a Cape town to Nairobi tour that crosses 7 Countries. 48 days and 5,200 miles! Not sure the price of that one but it would be nice to have a little backup on a trip like that. Especially at the border crossings.
I don't have anything to do with his company, just impressed by it.