We will be up in Cinque Terre and want to travel down to tour some wineries. I want to take the train to a city and hire a car service to tour. What would be a great place to stay? Arezzo? Another piece is that I want to hop back on a train to travel to Rome as we fly out of FCO. Secondly, what wineries?
Arezzo is not a good choice due to travel times to the wineries. Look at Montepulciano as a compromise between access to wineries and train access. I recommend searching this site as this question has been asked a lot and the variations are endless: https://search.ricksteves.com/?button=&date_range=1y&filter=Travel+Forum&query=tuscany+wine+tour&utf8=%E2%9C%93
Siena perhaps but by bus.
This is not what you asked, but if I wanted to tour wineries and vineyards, I would go to Piemonte rather than Tuscany. You could get to Asti, for instance, in 3 hours by train. All kinds of wine tours available in Piemonte. Fly home from Milan instead of Rome?
We are booked for Rome. Already have the Florence part along with going up to Cinque Terre. The open part is departing from CT and getting to the area to tour some vineyards. Trying to keep it easy on getting back to Rome for my flight. We have two days and our friends only have one.
Going back to Florence is best in your case. There are plenty of organized excursions offered by many companies in the nearby Chianti area. Actually, if you plan to be in Florence before the Cinque Terre, you might as well visit the winery while you are in Florence.
From Florence there are plenty of high speed trains that can get you to Rome in 92 minutes. But if you visit the wineries while in Florence, before going to the Cinque Terre, just take a train from Cinque Terre to Rome. The fastest go through Florence (FrecciaBianca) but some take the slower coastal rail route (not much of a view on that route since the train travels at least mile or so from the shore, except for very short segments where you can see the sea).
I know staying in Florence totally makes sense and that is what I figured I would have to do. Was hoping to get a country stay versus the city stay again.