I do not know if this exists, but I think recreational parascuba would be really fun.
I don’t think it would be practical (cost-effective) to use aircraft, and helicopters (my favorite way to travel) add some safety issues. However, parasailing is already done recreationally to a great extent.
So, imagine that you gear up on the boat, strap onto the bar, and then you and your dive buddy go up for a short parasailing ride. You then descend to a reasonable altitude, drop into the water, and begin your dive.
I know that parascuba exists for non-recreational purposes and not from a parasail, so it seems to me that this idea can’t be too far-fetched.