Hi Randall
In that case make it a Northern trip!
I’d suggest Venice as a starter, on the basis that you’ll be walking (or boating) everywhere, so a good option for overcoming jetlag, then get a fast train to Florence (2hr 5 min). From there it is possible to take public transport to (say) Alba, but no faster than the car, so I’d suggest hiring a car in Florence, for a drop-off at Milan Malpensa or Torino Caselle. Google says 4 hrs, but allow for a little longer if the weather is bad. I’d lean towards the Bologna/Reggio route, rather than Lucca/Genoa route, but maybe if a lunchtime stop appeals, that could dictate your route. I’d split it 3 + 3 + 4 in terms of days, but knowing that you may lose two half days with traveling (inc. check in and out). Of course if you do Florence + Langhe then you get more time in each, one less transfer and one less pair of checkin/out. It’s always a balance. Plenty of good agriturismi / apartments in the Langhe, but I’d make it a priority that there is a restaurant in walking distance for the evening. Driving in the dark is of course feasible, but much less enjoyable than relaxing over a good meal with good wine and maybe a grappa or digestivo to finish, only worrying about the short walk back.
As well as the jet-lag thought, this route means you’ll have you bags at the heaviest at the end … when you have the car. That is presuming you’ll want a few souvenir bottles to take home.
I’ll lean on others for suitability (December visits), but there is always work to do in the winery, so they tend to be staffed all year round. You could always check with the excellent tourist office langheroero.it, who last time I checked also had a booking service (free but a fair penalty fee for no shows). One thought for arrival in the Langhe, that a hr+ drive the previous day might make it lovely to take in a walk to a nearby winery in the afternoon, or even make the following morning a walk to wineries plan. The weather may make walking through the vineyards too difficult (which is a shame to miss out on) but quite easy to plan accommodation + winery visits with this in mind. Might make the driver feel appreciated / not feed up of driving.
Having the car does give the option of a stopover, but that will eat into your days, and add another checkin/checkout which for me is wasted time (unlike sitting in a bar with a warm coffee, which isn’t wasted time IMO!). One place I’ve not been, but plan to go is Tortona. This is the city nearest to the vineyards that grow excellent Timorasso and looked interesting from the aerial shots from the Giro d’Italia last year. Might be an option.
As for driving, the autostrade are generally good if a little poorly maintained, though there is a good new stretch near Asti. The biggest tip I’d give is to recognise that when turning off at an Autostrada junction, the turnings invariably become surprisingly sharp, and the seemingly slow recommended speed is entirely sensible. Driving in the Langhe is fine, though not ideal if tired, due to the hairpin bends.
Regards
Ian