First, create a route on your map that has you traveling from one island to another (Make sure you are crossing a bridge along the way). Next, hail a cab, jump in, and select "way point" as your destination so that the cab follows your route that you created. Now, instead of skipping the entire ride by pressing A, just sit back and wait for it to complete the trip. By the time your trip ends and you get out, the achievement should unlock.