For the Get Wrecked Achievement you need to get the various routes for the new Merchant shipwreck voyage.
The issue is that I have so far been unable to get the route that starts from Brian's Bazaar with the Roaring Trader's destination or vice versa.
According to several posts on trueachievements.com others are having the same issue with someone claiming to have put down nearly 100 voyages and still not get that route. I think I've put down at least 10 over several sessions. I even tried one of the suggestions to go up behind the DR fort to trigger the voyage. I've tried being directly next to either Seapost, someone in between, etc, etc.
It would preferred it this could be resolved by increasing the chances of getting this route by being near either Seapost as it is with nearly all the other routes.
I submitted a ticket yesterday about this too.
reference: https://www.trueachievements.com/a320418/get-wrecked-achievement?showguides=1