The best place to try for this achievement is down by the helitours. There is a queue of people waiting for the next flight, standing behind a rope barrier. If you are fighting over the rope barrier you take very little damage when you are hit, and also you are close to a hotdog seller to heal up when you take too much damage.
Your stats will record a counter as each time you duck out the way of an attack, but I think the achievement only records a counter if you also hit the person after ducking. I had to make 25 counters in my attempt before the achievement came up, but a lot of those I didn't successfully hit the person after ducking.
Lock onto your target with Left Trigger, then learn their animations and press A to avoid their punch, then press X or Y to throw a counter punch/kick.
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