We're staying in Montalcino in May. How much time should we plan to spend in each town. For the most part, we're looking to get a general feel of each place - sit in the square, check out some shops, enotecas, and churches.

Spello
Assisi
Montepulciano
Cortona
Pienza

Grazie!

I'm not clear on what you mean - if you are staying in Montalcino, then the other places would be day trips, right? Are you asking if you should return to any of them more than once? They are all small enough to visit the "sights" in one day, Assisi has the most sights and probably deserves a second day for that.

Spello and Assisi are about 2 hours from Montalcino so that impacts the length of visiting time on any day trip.

If your plans are not fixed on Montalcino for the entire stay, I would consider staying there for half the trip and then moving to Spello or Assisi for the second half. That would reduce and allow you to get the fell of two different towns/areas at the same time. Cortona is midway between the Montalcino/Pienza/Montepulciano and Spello/Assisi town clusters so it could be seen from either of them at the same time cost, or on the way from one of the clusters to the next..

We love Pienza and have been there many times. On the other hand, it is small and you can visit the whole town in an hour or 2. On the other hand, Montepulciano is a much larger town and there is a long (and delightful) walk up to the top. It will take a half a day, and is also worth revising, but that's up to you and your time schedule. There are several good restaurants in Montepulciano. Cortona requires 2-4 hours, depending on what you do, and Assis - half to a full day.

Check out our trip to Tuscany in 2005:
http://www.travel.stv77.com/tuscany2005/tuscany05.htm

Sorry for not being clear. We will be staying in Montalcino and would like to do day trips to the various towns and didn't know how much time to allocate to each town.

Thank you ssssteve for your information and for sharing your trip!!!! I haven't read it yet, but printed it out so I can read in between meetings today. LOL From what I saw, it looks like you had an amazing time.

Spello - 3 hours
Assisi - minimum one full day
Montepulciano - half a day
Cortona - 2 hours (highly dispensable, though, IMO)
Pienza - 1 hour
This is about thorough sightseeing only; no time assigned for gelati, caffè, tramezzini... (and you should absolutely have gelato in Spello - there's a justly famous gelateria just outside one of the Roman gates).

Pienza - small, but a charming town. I suggest 1/2 a day including lunch.

Cortona - I agree with franco - "highly dispensable" - I could have skipped it. It just wasn't that thrilling to me. Much more like a city than a "town"; lots of tourists. We enjoyed the Etruscan museum, and had a delicious lunch, but then moved on with our day.

Montepulciano - we based there for the week. Loved it! Depending on what you want to do you could spend a couple of days there (or more!) Lots of wine shops and tasting rooms, many restaurants and caffes, lots of churches, the Piazza Grande with the Duomo and Palazzo Comunale.

Enjoy your trip!

Start with a map. I see 3 of those as too far for a day trip-unless you plan to stay in Umbria as well. There is plenty to do within an hour of Montalcino--you do not need 5 hour driving roundtrips into Umbria. Plan on one day in Siena and see Abbey Oilveto Maggiore coming or going.

By the way, in Pienza, if you visit also the old Pieve di Corsignano church (which is about 1 kilometre outside the walled town), then you should add 45 minutes to what I said above. It's worth going there.