What about attaching an inflatable lifting bag to the anchor, then running a hose side-by-side on you anchor chain (attached by cable ties) down to this lifting bag, and at last having a small compressor in you boat.
This way you will get the anchor up, and you only have to lift it over the tubes. (Could try with helium to see if you could get it to fly into the boat)
As for the "Hey look what I have" thing, then you can just tell all your buddies, hey look is that my anchor floating out there
We do it when diving, but then you have to go down there to inflate it.