It was fairly hard to get DS to try new things as a kid but it is getting better. We're also a pretty adventurous family and love to get out and do stuff and travel. Some things we've tried to various degrees of success
- bribery - want to go for a bike ride? No, ahhhh but what if we bike to the bookstore and you can pick out a new book or we bike to get ice cream (oh the things I thought I'd never do as a parent...)
- baby steps - canoe camping is too much? maybe start with sleeping in a tent in your backyard, then car camping at one of those crazy campgrounds that have a million activities/toys/etc, then camping at a provincial park and then finally back-country
- brainstorm together to list a bunch of activities and let them help pick - you can start with some of the baby step ideas. We did this a couple summers ago and did a couple new things a month. Not all of them were crazy but we had a lot of fun.
- be active in the city and/or local parks - so many options where you can be active and build the confidence to maybe venture out of the city eventually. We've had a blast geocaching in our neighbourhood which is pretty low risk for bears
- recruit friends - DS never ever wanted to skate until we asked him if he wanted to sign up for skating with his favourite cousin and then he was all for it. We then used that success to build on and try other new things.
The other thing to think about is if it is better or worse for him to have the younger more daring sibling learning something in parallel. Sometimes it has been good to have our DD who is far more daring doing it because DS then does it to compete but I can also see it easily backfiring if DD were to catch onto something quicker and he wasn't.
Good luck! We've now managed to do some pretty cool things but it definitely didn't happen overnight.
