Two rules: Keep it easy and pair it with treats

My gauge of an activity's difficulty is always off of my friends' scale. So if it we followed my inclinations, they'd be exhausted, frustrated, overwhelmed, over their heads, and never accept my invitations ever again. As a my adventure buddy's girlfriend put it, "Don't break your friends". By keeping activities relatively easy and short, you're guaranteed to get most of what you like. And your friends will be more likely to enjoy themselves 

The other half of this is the 'commitment device' strategy. If your friends aren't inherently motivated to do that activity, pairing something positive you KNOW they like will sweeten the deal.

Examples: a hike that ends at a brewery, a snowshoe hike with a warm thermos and rocking picnic items for the scenic lookout, a bike ride to that pizza place that never has parking anyways. Also giving them some of your best gear can be a big help 🙂