Stabilized delivery using an Unmanned Aerial Vehicle (UAV) is described. In one embodiment, the UAV includes a flight controller configured to control a flight path of the UAV, a winch mechanism secured to an underside of the UAV, a platform tethered to and extendable from the winch mechanism, and a ballast system configured to stabilize the platform. The winch mechanism may be relied upon to drop an item for delivery without landing the UAV. The winch mechanism can include a first winch mechanism secured to the UAV at a first orientation and a second winch mechanism secured to the UAV at a second orientation. Because the winch mechanism may give rise to certain design and operating considerations, various active and passive flight and/or ballast control systems are described. These systems maintain an orientation of the UAV, the platform, and/or the item during one or more stages of airborne drop delivery.