Pienze vs Montepulciano

I, personally, pefer Monteppulciano. Much of Pienza has been modernized.

I wouldn't miss either. Pienza is a Unesco world heritage site and it's beautiful. Both were my favorite weekend getaway from Florence when I lived in Florence. There is nothing modern about the historical center of pienza. It has been the ideal renassaince town since Pope Piccolomini developed it 500 yrs ago and it hasn't changed since. Never gone to the area by public transport. Car is advisable. In montepulciano or pienza There is a bus connection with the station Chiusi scalo along the Roma Firenze train line. This is the closest and best station coming from south. The bus company is Lfi (la ferroviaria Italiana). Coming from Rome this is probably the best option. There are also bus connection w/Siena w/ bus co. Called TRAIN (trainspa.com) bus to Montepulciano with stop in pienza. Siena probably offers more options since it's the provincial capital. There is also a train station in Montepulciano on the buonconvento line. I'll look it up further when I have a little more time tomorrow. However if it's a few people traveling together it's best to rent car in Rome, for example and drop off in Florence. You'll get to see twice as much in the same time between Rome and Florence. Pienza and Montepulciano can be both visited in just a few hours. With a car you have a plethora of other towns you can visit in 3 days. With buses you are very limited in the countrysidebecause service is infrequent.

Great information! I am traveling solo for the most part and am not comfortable renting a car. My parents JUST returned from Montepulciano and said parking was a nightmare...throughout their stay actually. Are you thinking 3 days is too long without a car to get around? Grazie!

I realize the historical centers may be closed to vehicular traffic, but I never had any problems finding parking outside the city walls in Montepulciano or Pienza. You can probably walk the whole of Pienza from end to end in 10 minutes. I used to visit those towns on Sundays from Florence, as a day get away. I used to arrive at Pienza late morning (it takes about 1 1/2 hours from Florence, via Bettolle), visit the historical center as soon as I arrived (you can hit all the sites before lunch), then have lunch just outside the City Gate. Don't remember the name of the restaurant, but they used to make an amazing "Pasta al sugo di noci" (walnut sauce). Then I would continue my drive to either San Quirico and Montalcino (for some Brunello) or back to the opposite side to Montepulciano and/or Chianciano. First stop for me was always Pienza. Couldn't miss that pasta with the walnut sauce. I'd be back home in Florence by dinner.
What are you going to do 3 days in Pienza or Montepulciano? Drink all the wine around there? (that wouldn't be such a bad idea, though)

Paige, Parking is difficult in Montepulciano as in several hill cities. We had had heard that and were glad we had a reservation at a hotel there named Alberto Duomo (in Rick Steves' Italy book) in Oct 2012. This hotel had free parking included about 200 meters from the hotel. We were driving there under the direction of our Garmin and the Garmin routed us into the city on a route that no sane person would ever take - it was up a hill of 15 degrees within a congested area - filled with switchbacks. Our 75 hp Fiat Panda had MAJOR difficulty climbing the hills in 1st gear. We finally made it to the top and got to the hotel. The hotel owner/manager (Saverio) drew the circuitous instructions for me to the free parking (200 m walk but probably a 1 kilometer drive) and could see from the look in my eyes that I would probably not get there. He then suggested that he drive me there himself - which he did - and life was much better. On the drive there I pointed out the hill we climbed to get to his hotel and he said 'no one takes that road'. Saverio had a nice, reasonably priced hotel with a nice lounge, nice breakfast, and helped us with dinner recommendations. His free parking also solves the parking problem (if you enter the city on the correct route). Good Luck