Pienza to Cinque Terre

There are so many wonderful places you could see between Pienza and CT depending on the route you take and the amount of time you have. Could you clarify if you're looking to make the trip in one day and just looking for a short lunch stop or something of the sort? Or do you have multiple days to spend exploring the area?

Also, when you ask about "towns of interest," it would be help to know what you're interested in. History? Art? Architecture? Natural scenic beauty? Hiking? Food? Wine?

You might also search this site for discussions of Carrara, which is close to CT and the home of Carrara marble. Maybe that would be of interest to you?

It would most likely be a one day side trip. Art and architecture are our main interests but Carrara sounds like it would be interesting.

So, if I have this right, you are doing a day trip from Pienza to 5 Terre (and then coming back the same day). That is a 350 mile round trip. I don't think I would do that in a day.

Now if you are going to stay somewhere that is a bit different. I would drive up to Lucca and spend a night (great town). That is 120 miles and then the next day into 5 Terre (50 more miles or so).

Alternatively a drive through Tuscan countryside to places such as Siena, San Gimignano and Volerra, to Pisa. Stop in any of those for the night.

Gordon,
I implied the OP's post to mean they would be staying nights in both Pienza and Cinque Terre town and asking about stops along the drive.
Not that it was a day trip or that they wanted to stay overnight anywhere else but until the OP clarifies we would all be guessing.

Stopping to visit other towns on your way usually means luggage in the car which can be risky.
There are plenty of options though, all of the towns Gordon or Lane mentioned could be visited for a few hours in route making a full day out of your journey from hotel in Pienza to hotel in Cinque Terre.
I would choose one not multiple things to see. Most towns you will need to park outside of town and then walk into town to visit so what you think might be a 30 minute stop to see something could take 2 hours to actually do it.

For most places in Cinque Terre it is advised to drop off the rental car in La Spieza or pay for parking at the garage underneath the train station in La Speiza and train in from there to avoid driving into the Cinque Terre and paying for parking multiple days when you car will be unused anyway but if where you are staying is one of the few with parking and you are driving somewhere else after or other obvious need for a car I can understand why you would drive all of the way there. Just please look into it first most everyone will recommend against driving there.

No no.. never in one day. We're still juggling our days & areas. We're flying into Bologna since this was the cheapest for us, then renting a car to drive to Florence. Spend possibly 3-4 days there, then onto Pienza where we've booked with an agritourism for a week (we'll see Sienna one of the days while there). From there we were driving to Cinque Terre where we only plan to spend a day since not all trails are open. We have a day or two free that we thought we'd look around the area before heading back to Florence/Bologna. We're flexible with the order of things except for Pienza if it would be better to see Cinque Terre first before Florence. Still working on this and would appreciate your input.

Be much better to use the train from Bologna to Florence and then rent the car when leaving Florence on the way to Pienza.
Florence is surrounded by ZTL's and even if you can drive to where you are going parking is usually very expensive.

For your trip, the only time you will want a car is the week long farm stay outside of Pienza.

As far as Cinque Terre, I don't think it is worth going out of your way to get there to spend 1 night. Spend 2 nights or don't bother or day trip from somewhere closer. Don't think you will be happy hauling your luggage into one of those towns and likely up steps to where you are staying, only to check out the next morning.