My wife and I are currently staying at an agroturismo in Monteroni D'Arbia and are trying to decide what to do with Sunday and Monday. Please keep in mind we already spent three days in Florence and visited San Gimingnano on the way here. These are the options we are considering:

- Full day in Siena (this seems like a must)
- Day visiting multiple hilltowns (Montepulciano, Pienza, Montalcino)
- Perugia (farther drive but we LOVE chocolate more than wine)

Any advice?

Love Siena and Perugia!! But I wonder if you have seen much of the smaller towns?

My wife and I are 35/31 and are very much city folk. We loved Venice and Florence and so far find ourselves bored to death here in the country. Not sure how many small towns we'd like to see or if they will all seem like San Gimignano to us.

Since you've been to my favorite (Venice) and are farther south now, I don't think you will go wrong with Siena or Perugia -- in the latter, although the universities seem to be a bout outside of the old center, the hilltop ancient center has fabulous views, architecture, a wonderful passagiata (evening stroll), excellent restaurants, museums, etc. If you are by train there are cute little red shuttles from near the train station to get you to the upper town. There are also unobtrusive escalators to get you up and down. Several nice hotels too.

Siena of course has the communal living room of the campo, the cathedral/museums, again great cuisine, shopping, walking....

There's also Arezzo to consider, speaking of cities with Etruscan roots, and Lucca is a moderate size. But i prefer Siena and Perugia, personally.

From that location I would plan one day in Siena and the other visiting Montalcino and the Abbey at St. Antimo with a short stop in Bagno Vignoni coming or going.
Have fun !

There are artisinal chocolate makers in Tuscany, and probably many other places you are going in Italy. Do some Google searches for "artigianale cioccolato toscana." Perugia chocolate is my favorite in Italy (tho I've not tried them all), but I think it is not a great idea to speed past so much interest and charm to get a chocolate fix in Perugia (which is an exceptionally difficult Italian city to drive into.)

The main reason Tuscany has become a word known all over the world is the beautiful scenery, and the hidden small towns that have remained unchanged for 400 years. An art critic I once read said that there a hundreds of places you can stand today in Tuscany and look at the view, and it has remained unchanged since the times it was painted by artists during the Renaissance.

You don't have to go to Tuscany to see what made it famous, but it really hasn't been the cities. It's been the beautiful vistas of the landscape. The towns are just an excuse to stop.

bob: I'm not so sure they'll like St-Antimo if they're committed city-philes who are bored to death in some of the most beautiful, history-rich countryside on earth, but I agree a day at a spa might work for them.

http://goeurope.about.com/b/2010/01/...ate-routes.htm

http://travel.nytimes.com/2007/11/04...4journeys.html

http://www.foodandwine.com/articles/...best-chocolate

http://www.amoretravelguides.com/blo...is-home-to.php

Some of those articles are more than a few years old, so check for possible changes in location or opening hours before you set out.

I was in this area for the first time this past summer. I was smitten by Sienna (and didn't get to spend nearly enough time there).
I also loved the coastal towns of Cinque Terre. These are 5 small towns nestled in the hills on the sea. There are hiking trails that connect all five of them together, and small trails around each one. The hills are filled with vineyards and olive trees. This is a beautiful area that I would return to in a heartbeat. http://www.ricksteves.com/plan/desti...inqueterre.htm

What a horrible post, St Cirq. What's wrong with you ? You're the one who thought Umbria was just one big spa to splash around in. Not everybody is going to find wallowing around in self-indulgence and photo-op twee Europe something they can turn into a life project of whiney, longing bitterness. They've probably got too much energy to settle for cliches.

cdispoto,

I owe you an apology because i didn't see your second post. Only your first. Now that I have seen your second, I congratulate you on your candor. San Gimignano has lost all its life. It is practically nothing but a tourist trap these days -- especially if no one told you to go inside the churches and see the art. I also happen to think rural Tuscany is a place to drive through, not a place to stay for days on end. I do find it delightful seeing in 3-D the vistas I've seen in Renaissance art. But for nature, I'd rather be in the wild, not a place where all the trees were ripped out and rearranged with obsessively laid out cypress rows.

After a while, you begin to understand why it's so popular with affluent American suburbanites. It's their ideal gated community, where nature has been de-naturalized.

If you opt for Perugia, please do get some good driving directions to it, available on Slow Travel. (Don't tell them why you want it. They are mainly Tuscan ideologues too and obviously what you are saying is heresy.)

You might give serious consideration to Arezzo, or if you take the chocolate trail, stop into Pisa and tour the town away from the Leaning Tower (itself very beautiful, but encased in the worst tourist scene in Italy outside of Venice and Capri).

Hope you are headed to places more congenial to you than "Tuscany" on this trip. Some great cities if you haven't been are Athens, Lisbon, Antwerp (great for chocolate).

By any name, it is sad to see such negative, contrary reactions to others opinions. She must be very sad in her ex-pat life in Liguria. Perhaps we should all just disregard and pray for her health and happiness and concede her superior knowledge. It is just so sad.

Monteroni d'Arbia to Perugia is more than 90 minutes each way, plus time to park and get to the center. For me, that's too far for a day trip. (But I do understand the chocolate craving.) Arezzo is a little closer. Not sure why Pisa was even mentioned. It's more than 2 hours each way from Monteroni d'Arbia.

Siena has grown into a good-sized city with lots of traffic. I have no idea whether you'll enjoy it more than San Gim, but FWIW we didn't like San Gim much either. Have the people at the agriturismo give you directions for the best approach to Siena, where to park, etc.

We love cities too, but we enjoyed driving between the towns in southern Tuscany, Montepulciano to Montalcino, stopping/detouring for anything that looked interesting.

Then again, the OP first posted about 24 hours ago, so I suppose decisions have already been made.