I've given Milo some rawhide bones, but the same size I give Zeus which is about a foot and a half long bone, spends ages on it, and it he gets a flappy bit that's all soggy he jumps around throwing it in the ai, rather funny and cute to watch, but I always have a close eye on him just incase he does eat bits.

Also I've found with Milo Pedagree Denti-Stix for the medium size dogs good for him... Okay about 10mins of him being quite, unlike his sister who wolfs it down.

You could also try a hockey ball, extremely tough, Milo loves kicking that around, and an added plus is that Zeus *my 3year old boxer cross* can't chomp it in half, like every other supposed "unbreakable" toy :/