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Italian hill towns - Need Recommendations


I was wondering if someone could give me pointers on which hill towns to visit in Italy. So far I have read great things about Siena, San Gimmigano, Lucca, Orvieta and Cortona. I will be picking 2 or 3 of these (or let me know if you any other suggestions).

My main concern is that I don't want them to be very repetitive. Could you suggest a good combination?

Thanks in advance!

Posted by
705 posts

I can only comment on San Gimignano and Siena. The are both interesting and lovely towns and are often linked in day tours from Florence. I'm sure you would enjoy a visit to both.

Posted by
18 posts

We just got back 1 week ago and we went to Volterra,San Gimignano, Montepulciano, Castellina in Chianti, Radda in Chianti while based in Siena. Siena is wonderful. The hill town we liked the best was Volterra. It is higher in elevation than most of the others and the views from there were amazing.The Chianti region was beautiful.If you should go to San Gimignano look for the prize-winning gelato place.It had the best gelato we had. We rented a car and were glad that we did because there are many very scenic roads. You will love it there!!

Posted by
14 posts

Each town has its own history, festivals, people, personality. Think about what you are interested in, where you might have friends, acquaintances, contacts who can give you an insiders' view.
Please dont try to "do" a certain number of towns just because everyone else has seen them. You'll only get out of your travels what you "put in" beforehand.
San Gimignano has towers- so does Viterbo and many other towns.
Orvieto is built on a rock outcrop- why? what's underneath?
Cortona- what's nearby? who were the historic families?
Lucca- why are there the huge walls surrounding it?

Posted by
49 posts

I went to Lucca, it wasnt really planned but Florence was very hot and crowded in mid-May and I wanted to escape for the day! I went to the train ststion and checked the departure board to find the next train that was leaving for someplace I had heard of. And that was Lucca! I loved this charming town, it was flat (no hills! no stairs!), cool, friendly, little traffic, beautiful churches around every corner, very quaint. I spent a day being charmed by this un-touristy town within medieval walls.

Also went to Siena, it was a wonderful day trip. So many maze-like alleys, the gorgoeus campo, and the magnificent Duomo....

Don't know if Pisa is a hill town but I enjoyed visiting it!

Posted by
5 posts

Hi Meetu! you're going to have a wonderful time!

Personally, I think Siena is a must-see. You can see the main sights in a few hours, but you could also spend a day. It's a town with NO SHADE so be prepared for the sun to zap you and make you more tired than you should rightly be. :)

Last May some friends and I did four hill towns in a day: Montalcino, Pienza, Montepulciano and Sarteano/Chiusi. The two "M" towns are a must if you like wine -- lots of little vineyards. However, Pienza was our hands-down favorite hill town. There's one main "drag" of shops to pop in and out of, sampling pecorino cheese (this is where pecorino comes from - it's great to buy some and take it with you for your next stop). I can't say there's tons of things to "do" but it is such a charming place!

Finally, I'd recommend Volterra. It's The Town That Tourism Forgot. Great ruins, great views, and a great big park that's great for just relaxing, picnicking and soaking up the local atmosphere.


Posted by
226 posts

I've been to a number of the towns mentioned and agree that Siena is a must-see. Because it is larger than all the others, it has a different feel and character. Personally, I'd label San Gimignano too touristy and would favor one of the other options. Although you won't avoid tourists in any of the towns, San G. is smaller and its main drag is usually mobbed. I stayed in Siena for a week last month (as I did last May) and loved every minute--used it as a base to visit Montepulciano again as well as Pisa (not a hill town) and Florence (one of my least favorite places in Italy).

Posted by
5 posts

i've been to florence several times now. my suggestion is stay in florence, i always stay at soggiorno battistero, you can find it online. kelly is very helpful and an american. nothing fancy,but very clean and in the center of everything...and relatively inexpensive. from there you can scoot to lucca and spend the day by bus,ride bikes around the fortress and shop, neat little eateries, very easy. only 1 hour away. then on another day catch bus 7 from any florence bus stop and 20 mins away go to fiesole. very cool up there on the hillside. several times i wait to get up there, buy some lunch meat, bread, fruit and so forth and go to the top of the hill and have a picnic. great florence view from up there. this gives you a great experience with some hillside towns and you don't have to pay for another hotel. of course the big towns are nice too, san gimmigano and so on. the cathedral in siena is worth the extra trip. un-freaken-believable...kat

Posted by
466 posts

Been to Siena and Orvieto and both are just beautiful!! I would recommend both of them. If you are interested in the italian ceramics (pasta jars, plates, biscotti jars etc.) you will want to visit Orvieto. Lots of pottery from Tuscany!!

Posted by
306 posts

Love Siena, Voltera, Montalcino etc but our very favorite is Pienza. The views are great, people friendly, great restaurants, a comfortable town to walk around. We fell in love with it and have gone back numerous times.
I like Lucca but to me it doesn't feel like a hill town.
I don't think any of the towns on your list will seem repetetive.