Living where I am I know quite a few guys who combine a biking holiday with taking the wife as well. And there's two types!
Those who come over with their wives on the plane and hire a bike on the days they want to go out.
The other type (which is the most popular) is the wife flies out......and the guy rides out, usually getting here before she does. Then on the return, she flies out......then he leaves.
I meet up with a guy who does this every year......and he brings his dog Buddy on the bike. I'm seeing him again in September.
Apart from guys with little trail bikes that can't do distances, or track bikes that are not road legal, I've never heard of anybody doing it your way.
It's a bit Sturgis "Trailer Queen" for me!