Siena to Montelpulciano & Pienza - which is the most scenic route to take?

As long as you avoid the SS73, you can't really go wrong with scenery.

Here's one I find kind of fun:

SR2 to Buonconvento. SP451 to Oliveto Maggiore. SP60/A to San Giovanni d'Asso. SP14 to Montisi. SP71 to Castelmuzio. SP71 to Pienza. SP146 to Montepulciano.

You can try something different going back.

Here's a difference of opinion.
I love the drive on the 73. It also takes you to the farthest location first, Montepulciano.
It's also the largest, so you might want more time there.
Then take the 146 to Pienza.
Leaving Pienza, and if you have time, stop at the spa town

https://www.visittuscany.com/en/ideas/bagno-vignoni-hot-springs-in-val-dorcia

For a quick look around.

Maybe stop in Montalcino for dinner, then head back to Siena.

Thanks guys!!!
The drive to and fro montepulciano was wonderful!

Which route did you choose?

IMO, it doesn't really matter which route one chooses. The area between Siena and Montepulciano is absolutely breathtaking. As long as you avoid the Strada Statale (SS) highways, which offer no shoulder lane, no ability to pull over and take a photo, you won't be disappointed.

The vast majority of tourists don't have enough time to explore all the "local" roads of Tuscany. They come onto travel boards asking for the most scenic route, not realizing that every single local route offers an abundance of surprise and visual excitement. IMO, all of the local roads deserve to be experienced. Most people would have a very difficult time picking the "best," once they've tried them all. You'll need more than a 3-night stay to accomplish this wonderful adventure.

KiM: i took NYCTravelSnob advice and did Buonconvento to San Giovanni to Castelmuzio to Montepulciano.

NYCTravelSnob: Completely agree! Almost every route is good...and with a GPS ..getting lost is kinda fun..as one still ends up at one's destination but taking a "surprise route"
3 Night was just a teaser..i am coming back for a least a week long stay next!

:)

Hi I plan on doing a similar drive at the end of this month with my elderly mother. I will be starting a little farther than Siena. Were you able to spend time in Montepulciano and Pienza and enjoy the scenery along the drive and not feel rushed? Recommendations not to miss along the route? Thanks!

If taking the SS highway, the drive from Siena to Montepulciano is about an hour. If you take the local roads and don't stop anywhere or get lost, it can take an hour-thirty.

Almost every town you drive through in this part of Tuscany will offer a new discovery, a variation on a view. If you decide to stop somewhere and walk around, the minutes will go by quickly. There is a learning curve to figuring out the lay of the land, learning the best/safest place to park your car, and figuring out how to exit and proceed with your drive, especially if you stop for lunch and have a glass of wine.

Parking distances from city centers can be further than expected. Some feel like a mile away. Walking to city centers from parking lots is often uphill. For some elderly people, these things are a challenge. I've seen many people struggle. If you take on too many stops in one day, it's easy to exhaust quickly.

For postcard views, the best time to be on the road is 6-9 AM. Most tourists with cell phone cameras miss these amazing hours of visual spectacle because they wake up too late and don't want to miss the breakfast that's often included in the room price. One hour before sundown is also spectacular, but you need to plan your drive with more care at this time, because most streets in Tuscany don't have street lights. Driving in the dark can be problematic.

Pienza is very popular because it's small, charming, and mostly flat. IMO, it has too many tourists, particularly the elderly, but for good reasons. The easiest way to enter the city on foot (flatter) is from its southern side.

Montepulciano will present a challenge for most people, especially the elderly. It's built on a hill and the hill is long and narrow, a bit more difficult to figure out and traverse on foot. The only area that is flat is the area around Piazza Grande, at the very top. If you park in the wrong lot, your walking challenges will increase. If you park at the base, the walk up can be deadly.

Each city has a ZTL zone at the very center, which can complicate the process of finding the best, most convenient parking lot.

Good road research before your trip can save a visitor time, energy, and a boat load of frustration. Google Street View is a tool worth learning how to use.

lsd1980s: Thanks! It's great that you came back and reported!! Glad that you enjoyed it so much, and thanks for the info.

mvj: I didnt stop at Pienza unfortunately.

I did spend some time at Montepulciano and even had time to do a quick stop at Siena. I didnt feel rushed at all. I was with my relatives who were in their sixties with some slight mobility issue. - the uphill walking took a toll on them...but they enjoyed it.

Could i spend more time? Absolutely! 3 Days is way too short - but we all have our limitations and what i saw only whet my appetite for a return trip.

I think just driving leisurely and stopping whenever you feel like it might be my recommendation.

Kim: No problem! This forum has helped me plan a trip from scratch and would love to give back whatever limited knowledge i have.

lsd1980s