A gyroscopic roll stabilizer for a boat includes an enclosure mounted to a gimbal for rotation about a gimbal axis and configured to maintain a below-ambient pressure, and a flywheel assembly including a flywheel and flywheel shaft, with the flywheel assembly rotatably mounted inside the enclosure for rotation about a flywheel axis. The gyroscopic roll stabilizer also includes a motor operative to rotate the flywheel assembly and disposed inside the enclosure. A motor cooling circuit is configured to transfer heat away from the motor. The motor cooling circuit has a closed fluid pathway for recirculating cooling fluid therein. The fluid pathway includes a fluid channel jointly defined by the motor and the enclosure and having the cooling fluid therein. The gyroscopic roll stabilizer is configured to transfer heat away from the motor to the cooling fluid. Related methods are also disclosed.