Myself and four other blokes are doing Launceston to Hobart via the east coastover two days between Christmas and New Years.
If you’re after wineries, the north east corner of the island is your best bet, some not all that far from Launceston. Pipers Brook, Rosevears Estate are a couple that come to mind, but there’s quite a few. Remember; vineyards like hills, so that might give you an idea of terrain.
There’s also Ironhouse Brewery between Bicheno and St Helens on the east coast, they have accommodation there, that’s where we’re staying at the halfway point.
There’s a good pub at Weldborough, which is kind of in the middle of nowhere, that serves (only?) Tassie produced beer. I think they might have accommodation too.
Most of the towns down the east coast have associated Motels - St Helens, Scamander, Bicheno, Swansea. They’re quite quaint and worth stopping at if only for a bite to eat or drink.
From Scamander south it’s reasonably flat if you stick to the coast.
There’s some great windy roads St Marys Pass and Elephant Pass, but I reckon they’d be pretty hairy descents with not much shoulder, and they probably wouldn’t fit into your route that well, but if you were keen you couldclimb up St Marys Pass and descend Elephant Pass.
I think the road condition is pretty good as a general rule, although there’s not much of a shoulder outside of the towns, but the trade off is traffic will be fairly thin. I can tell you more when I get back.
You won’t be far from Port Arthur which is worth a look and Richmond is a historic town if you like that kind of stuff.
Avoid bogans, and there’s plenty of them, but the worst you’ll probably get is a few ‘sick burns’ from passing vehicles.
Happy to meet for a coffee/beer to discuss further.