This experimental study aims to investigate the effect of different pocket milling strategies and cooling conditions on milling force, temperature, tool wear, and surface quality when machining AZ91 magnesium alloy. Four tool path strategies have been evaluated contour strategy from inside to outside, contour strategy from outside to inside, hatch+finish strategy with an automatic optimal angle and hatch+finish strategy with a user-defined angle. All pocket milling tests have been conducted in different cooling conditions that are dry, coolant, and air blast. Milling force, temperature, surface topography and tool wear are measured in an experimental study. The experimental results show that the best tool path strategy is hatch+finish strategy with the user-defined angle, while the worst tool path strategy is hatch+finish with the automatic optimal angle.