You have to deal with two view controllers one that's in the background called mainController one that presented using a UIPopoverViewController called popoverController. Your popoverController could add a UIPanGestureRecognizer to the views, that the user can drag. The action target of the gestureRecognizer could be a method on the popoverController.
According to the documentation on UIPopoverController, when the popover is presented, it is presented on a special "window". Because of this, simply adding a subview to the popover view controller's content view controller is not sufficient to be able to drag a view outside of the popover view controller's view.
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