Originally Posted By balzaccom
My suggestion is to take him on at least two shorter trips (ideally in a variety of conditions) before attempting anything close to what you are considering.

And be prepared to bail if he's unhappy. The trip is not as important as your relationship.


I second this advice. Even after a couple of short trips, he might discover that he doesn't like a long hiking trip. So it would be good to have options for leaving part way.

Chances are with his canoe tripping background, he'll love it. Yet another way to have an outdoor adventure!

Good luck and
Have Fun,
-Bob