This is easily done with a partner on LIVE, or in a local match with two controllers.
When you start, choose 8 destination cards, preferably all on half of the map (Duluth is roughly midpoint on the North America map). Your partner will take the minimum and every turn will choose just one destination card until he runs out and then switch to drawing railway cards. Once you have 8 destination cards, focus on drawing railroad cards, always drawing two face down cards until you have 60 cards. Once you have enough cards, start placing railways, focusing on completing all of your destination cards. After all 8 destinations are completed, play any remaining railways you have left to end the game.
As long as you complete all 8 destination cards, the achievement will unlock after the final scores are displayed.