If you could spend three weeks in and around an Italian city or town, which would it be? Why? Think beyond Rome, Florence and Venice, nice as they are. Just looking down the road…

Siena--in other words, rural Tuscany.

I would think regions or areas rather than a single city or town. I think my husband would like to live in the lakes area for a year because of the scenery and variety of activities throughout the year, from cycling to skiing and from mountains to lakes to trails for hiking. I also love the lakes area, but Umbria would be a very, very close second. I'm a little more interested in cultural sights and the local cuisine.

Jean, your reply expresses what we're also most interested in...the cultural sights, the cuisine, the people (and a bit of nice scenery wouldn't hurt.) No nightlife! We're conked out by 10.

If you're conked out by 10, then stay in Pienza. No nightlife at all! This is not necessarily a bad thing. I was there for 3 nights and loved the town. I had planned to do a daytrip but ended up never leaving, partly because I was a little tired by the time I got there (having already been to Venice, Florence and Siena with stops in between), but more because I just enjoyed being there. Good restaurants, plenty of cultural sights in the town and just outside (much more than most people think, as the common misconception is that you can "do" the town in a couple of hours), beautiful views from the walkway on the south side of the town.

And of course there is the Pecorino cheese. Order the Grilled Pecorino whenever you see it on a menu! And buy some from the numerous stores in town to take home. They will vacuum pack it for you. Also some other nice shopping available if that interests you. In addition, it's the most flat "hill town," if that concerns you. And there are definitely plenty of daytrip options if you want to do that, especially if you have a car, but also some by bus. You would probably want to do some if you were there for three weeks! Let me know if you want the link to my trip report. You can skip to the Pienza part if you like.

Pienza- I like the incredible beauty of the Val d'Orcia, the Crete Senesi and the small, peaceful, almost deserted villages. I also enjoy hiking in the area and photography. I usually stay 2 weeks and rent an apartment (3 km outside of town) so that I can shop the local markets and prepare my own dinners. I enjoy a covered patio (alfresco drinks/meals) and being surrounded by great landscapes and changing light. I'm like you- out by 10 (but up by 6 or earlier- I can't wait for each day to begin!) I usually start the day with a sunrise run on a country dirt road.

Sorano/Pitigliano- For the same reasons, only a different landscape and food choices.

Bavagna- ditto. I really love exploring Umbria.

My favorite time of year- late May/early June and late Sept/early Oct.

Bologna or Mantova. Bologna because it's magic to me (still can't believe I'm actually going to be there again next month). Full of surprises, full of life. Just gorgeous.

Mantova because it's my favourite small town so far. I've been there twice each time for a day, and plan to come back one day and stay a whole week just relaxing and day tripping around the area. I love the untouristy atmosphere, and the town is just beautiful. And the pastries I was fortunate enough to taste: fabulous. As are the Ravioli di zucca - delicious.

<<And of course there is the Pecorino cheese. Order the Grilled Pecorino whenever you see it on a menu! And buy some from the numerous stores in town to take home. They will vacuum pack it for you.>>

I agree!!! Grilled Pecorino is fantastic!

Panicale or one of the remote spa towns in the Tuscan hills.

parkhill24, I don't want to imply there are no cultural sights in the lakes area. There are many, but for our interests we go to the area more for the outdoor activities.

My favourite Italian town? Definitly Siena, although Lucca comes close in my affections.

Be bored by the shores of Lake Como..great way to be "bored" IMO, nightlife consists mainly of eating, strolling, buying even more gelato...

So many to chose from.....
Lucca... lovely small town, surrounded by walls and nearby coast.
Perugia- large buzzing university town with excellent museums and galleries, good food and nearby towns of Umbria + Lago di Trasimeno
Bologna- another lively university town with wonderful food
Mantova - lovely old town with great palaces to visit- Renaissance masterpieces.
Urbino- hilltop town with the great Ducal Palace and surrounded by the Marche countryside.

Susan - could you please post your link? I'd love to see your trip report too!

I vote for Lucca. Adorable town, with the sea and rest of Tuscany within relatively easy access.

I have more, as I've been to Italy 7 times, but here is the one that includes Pienza:

http://www.fodors.com/community/euro...nt-like.cfm?87

We've been to Italy many times, and favor smaller cities. Now I think Bologna is my favorite because of the food, of course, but also because it is such an easy train ride to so many other places, including Florence, Ravenna, etc.

I'm in with the Siena crowd.

I'd have to agree with Pienza...right smack in the middle of what is, in my opinion, the most beautiful and relaxing part of Italy. A short drive to Montalcino, Montepulciano and other hill towns. Not too far from Siena and even manageable to Orvieto or Assisi (all towns that we drove to on our favorite trip a couple of years ago).

Sorry, but beyond Rome (which I would actually choose for three weeks since there is so much that I have yet to see there), this is really an impossible question. A bit like "which of the ants in this anthill do you like best?" It's impossible to choose from this wealth.
A short list with a bunch of possible answers, in no particular order:
Cividale del Friuli
Montagnana
Mantova
Pavia
Torino
Parma
Bologna
S. Leo
Urbino
Ascoli Piceno
Loreto
Montefalco
Perugia
Foligno
Sansepolcro
Arezzo
Castiglion Fiorentino
Certaldo
Pisa
Carrara
Alatri
Cori
Sutri
Tuscania
L'Aquila (as soon as it will have recovered from the earthquake)
Loreto Aprutino
Ragusa
Noto
Palermo