With the California rework now completed the required Vineyards are all Mon Coeur and are in Sacramento, San Diego, Fresno, and Ukiah. All of the vineyards are actualy well outside the city they are supposedly in. Fresno has a regular Mon Coeur depot that dosn't contribute towards this achievement, With the vineyard being the one further north.
I have yet to see a single freight market job bringing me to any of the vineyards, so the chance of earning this achievement during normal gameplay is very low. Specifically driving out to them to pick up a job or specfically searching for quick jobs starting at the vinyards is likely required for this achievement.
As of right now Steam is giving achievement progress notifications after each completed delivery from one of the four vineyards.