A physically-impaired-assisting multi-function sail comprises: a stanchion, a hoisting navigator for allowing an arthritic to deploy and retract the sail without the need to bend the fingers, a hoisting teeter totter secured to the navigator, a teeter-totter hook-lock secured to the teeter totter for automatically locking and unlocking the teeter totter to deploy and retract the sail, a cable secured to a camber, a cable canal formed into the teeter totter for hiding and protecting the cable within, a pivoting pulley housing secured to the teeter totter, a pivoting pulley hub swingingly attached to the pivoting pulley housing, sail-buttresses hingedly attached to the pivoting pulley hub, a sail canopy secured to the sail-buttresses, multiple cable pulleys rotatably secured at multiple locations within the pivoting pulley housing and pivoting pulley hub, a central tube attached to the pivoting pulley hub, sail-buttress-supporting arms hingedly attached to the sail-buttresses, and a shuttling hub attached to the sail-buttress-supporting arms.

An outrigger sail vehicle system includes: a vehicle, such as a bicycle; and an outrigger sail device, including a mounting base connected to the vehicle, an outrigger arm rotatably connected to the mounting base, a boom handle rotatably connected to the outrigger arm; a sail assembly, including a sail frame with first and second frame members, and a sail member that is spanned out by the sail frame; whereby, the sail assembly is rotatable from a right to a left side of the vehicle.

A sail system for a velocipede uses a swinging gate that pivots between a closed position, flush against the velocipede and an open position for sailing. A spring cord pulls the gate toward the open position while a control cord pulls the gate toward the closed position. A slide slidably disposed on a top tube controls positioning of the control cord and locks this cord in a particular position. A shield is also attached to the velocipede.