The Outfit

Transport Ship Destruction

Once you get to mission 6 go north from the armory and you will see three red ships, destroy all 3 and you will unlock this achievement.

When going through this game which I am highly recommending doing is using the Xbox Achievements road map made by CienPR, when you hit each level of the story just hit CTRL+F on the page and type the Mission you are on, and you will find the achievements you need to look out for and how to do them on each mission. There is about 2 each mission, and there aren't any videos which I would be posting if I could find some, but I guess this game isn't popular enough.

Again credit goes to CienPR, good luck and have fun

Road Map:

http://www.xboxachievements.com/game/the-outfit/guide/#

These are the achievements for Mission 6 of the single player campaign:

Mission 6:

Medals (Achievements):
1) Transportation Ship Destroyed
2) Submarine Destruction

1) After you capture the armory, go down further; closer to the water. There are 3 red oil ships. Use the anti-tank weapons to shoot them. You'll get the medal opportunity after hitting one. Shoot them all down to achieve the medal.

2) From the lighthouse, you can see the two submarines off to the right on the dock. Build a tank or an anti-tank weapon here to blow them up. Destroy both of them to achieve the medal.

Thanks to Messiadbunny for all the help!