siena

Several people told me I'd be bored with two nights in Siena, but I'm going back for four more because I liked it so much! I guess it depends on what you like, but I found the main piazza, Il Campo, very beautiful, especially at dusk. And walking the medieval streets was awesome as well. We're renting an apartment thru VRBO for 100 euros per night so I'm not sure about hotels.

I love Siena and I think 2 nights there would do it some justice. You can see the sights during the day and chill out at the Campo in the evening. I've been a few times but this past spring my husband and I used it as our Tuscany base for 10 days. We thought we would spend most days doing day trips but we ended up spending about 4 days just hanging out in Siena. It's great during the day, but fantastic at night. There are quite a few good restaurants too and they weren't too terribly expensive. We rented an apartment as we always do in town so i can't help with the hotel. I would check tripadvisor. They never let me down. If you are arriving by train, there's a handy new escalator in a shopping mall across the road from the train station that takes you inside town so it's not nearly as hard as it used to be. It's not well marked or from the looks of it well known. If you are driving, we found several garages just outside the ZTL (areas non residents can't enter) but very near the city center, and of course you can park at the underground deck at the train station too. Have a fun trip!

Robin, I agree with the others - two nights in Siena is definitely worth it (at least IMO). It's difficult to recommend Hotels without having some idea on your criteria. I'd suggest checking the Italy Guidebook to find lodgings that you'll be comfortable with. One suggestion would be to have a look at the website for Albergo Bernini. I believe they're under "new management" since I last stayed there. I did stop by for a short visit when I was in Siena last year and the new owners seem to be great. If things are the same, I'd certainly recommend staying there. Happy travels!

Siena, yes do stay overnight at least one night. As previous posters stated, the Campo at night is magical. I loved Siena. Also stayed at Cannon de Oro and although not fancy, in a very good location. Ciao!

Gives you a good jumping off point for seeing other nearby towns such as San Gimignano.

I visited Siena as a day trip from Florence and vowed to go back and stay 2 nights.

Yes - definitely worth it. In 2009 we stayed at Albergo Canon d'Oro. Not fancy but it's in an 800 year building so lots of character. It's within walking distance of the bus stop, Il Campo, restaurants, and pretty much everything else. We stayed there five nights (four days), with a day trip to San Gimiginano. Loved our time in Siena.

The answer depends on what you're giving up to do this, and what your interests are. Siena is indeed lovely, as are many places in Italy.

We were in Italy for three weeks in October and used Siena as one of our base locations for one week. We loved it! We stayed at B&B La Coperta Ricomata - www.lacopertaricomata.it. It was perfect. We actually stayed in a mini-apartment in the B&B. The owner Luciana was so terrific. She had stocked our kitchen with plenty of breakfast food and coffee and then every morning we would find a tray of pastries, yogurt, juice, etc. on our stoop. More food than we could eat! She also pointed us to traditional Sienese restaurants that were reasonably priced. We would have never found them on our own. It was very close to bus stops, and a easy walk to il Campo. I don't think you will be disappointed with Siena at all. If anything you may wish you had more than two nights!

Another vote for staying overnight in Siena. The streets are wonderful to stroll in the evening and some great restaurants. You'll see the city magically transform after the tour buses leave in the late afternoon.

Amen to what Douglas says. It's true of all the popular towns in Italy, whether you're talking about Siena, Assisi, Orvieto, Cortona, you name it. There are two towns - the ones the daytrippers see and the ones that the overnighters get to see. The overnighters get to see the magical side of these places. The daytrippers just get to check it off a list. There's a comment on another thread where someone daytripped into Orvieto and says that four hours was plenty for that town. Having spent two nights in that town, I couldn't disagree more, unless you just want to say you've seen the two or three most popular sites in that town. Happy travels.