It depends on what kind of tyre you're after. I don't know about cruisers, but I've found that on large "trail" bikes radials provide better mileage than crossplies, though crossplies are certainly cheaper. Although radials dissipate heat better (and hence don't get too soft) this would be less of a problem for you, based on the kind of riding you have in mind (and I think you have the right idea too; what's the point of riding a bike if all we do is hurtle through the scenery as fast as possible?!?). As far as "dual sport" tyres go, I've found that Bridgestone TW152 Trailwing radials are excellent on the back. They also have a very shallow profile compared with crossply Trailwings, so they conform more to what you were after. If they make a more road-oriented version, I'd go for those.
Tall men see everyone else's bald patch but their own.......