If you are entertaining, forget about putting on a lot of miles and getting a good wind up - unless, of course, you are friends and have ridden together and know what to expect from each other.
A "tour" as you explained it usually means seeing the sights and chatting. Plan that.
You might consider having him blade while you ride. Igor probably can do around 10 mph on blades pretty steady if he is in good shape. Tell him the route and milage you are thinking and ask him if that sounds about right.
I used to blade a lot and would bring my skates with me on trips around the world. It was a blast touring on skates and I could do 30 to 60 miles a day depending on the roads and the number of distractions (and depending on how many hours I put in). I actually did blade tour with bicycling friends. Bikes are obviously faster than blades. I was giving it pretty hard while the bikers were taking it easy.
Still, if you put aside any aspirations for a work-out and are patient, you could bike while he blades. Better yet, why don't you chose HIS dominant sport and blade tour with him? He might really enjoy that.