Extra night in Siena, Florence or Venice?

I'd add it to Venice. As far as staying up all night in Venice, you can but Venice is not an all night kind of place. There is stuff going on but not a bunch of nightlife activity after midnight if that late.

I'd add it to Siena - I'm a fan of the smaller cities

Stay up all night! You can catch up on your sleep at work.

Siena is the best of all!

Wow, I'm surprised by the two immediate pro-Siena responses. Small sample size, I know, but I expected Siena to be the least popular option. This is partly because most of the city raves I hear are re: Florence, Venice or Rome, probably in that order. Also some friends who recently visited Italy said they were underwhelmed by Siena. (But we included it in our itinerary anyway; Rick Steves likes Siena, and he hasn't let us down yet.)

From your earlier posts, it seems you are now expanding your time in Rome to 3 nights. I think you will be very happy you did! We, too, were underwhelmed by Siena. Since you are comforable with one night stops, you can easily see the highlights (Duomo, Campo), have a nice meal, and move on the next day. There is so much more to Venice. Spend your extra (3rd) night there so you have TWO FULL DAYS in that magical city. Ciao and happy travels!

3 days is the minimum a person should stay in Venice. Yes it is small and managable but there is really so much to see and do and most of it involves just getting lost. We did 2 nights in Siena but on the 2nd day, we took a side trip to San Gim and the chianti region. So I guess we could have done Siena in 1 day. But I found 2 nights quite neat there, that's for sure.

OK, I think we've got it. 1 night (2 half days) in Siena. Maybe a few hours in Florence (since we're passing through), then 3 nights in Venice. Now back to the Rick Steves books to figure out the lodging.... Thanks for the tips. Michael P.S.: Laurel, we're still just 2 nights (2.5 days) in Rome.

I'm one of those that just looooves Siena and have stayed multiple nights. So in my mind you can't go wrong adding a night there. I definitely wouldn't stay overnight in Florence since you've already been there. Just walk through the town and enjoy some gelato. But you can't go wrong adding a night in Venice too. Especially since the last night is so short. Flip a coin??

I'm definitely the minority here... I was underwhelmed by Siena, but couldn't get enough of Florence. So much so that I have no desire to head back to Siena at all. Florence on the other hand, I have been back 3 times each time wanting more time. I'd take Assisi or Lucca over Siena any day... My favorite gelato shop in the whole world is in Florence: Vestri, on Borgo degli Albizi :-) Florence deserves more than a few hours. Good hostel where I have stayed twice when traveling alone: www.academyhostel.eu Have fun!

How funny. Everybody seems to either love Siena or not like it at all. Maybe some parts are better visited and others avoided?

Theories of dislike: terrain. If you don't like to work out or you have back/knee/ankle aches and pains, Siena can be tough on a person. The streets and sidewalks are like 35 degree inclines. Some sidewalks turn into stairs. You make 1 wrong turn, you maybe have to deal with quite a tiring hike. If you did not prepare for this by working out or you just had no idea of how rigorous Siena is, Siena may be a disappointment for those with mobility issues.

If I had 6 days I'd spend 1 in Sienna, 2 in Florence and 3 in Venice. Sienna is a favorite of ours, but it is rally just a walled-in old town, cute but no art. There are other walled-in cities in the world. Rothenberg comes to mind. Between Florence and Paris they contain most of the Renaissance art we've seen in books. Florence itself is not as manageable as Sienna or Venice. There a too many scooters, hucksters and taxis for me to process. I've wandered Sienna and Venice late at night and both are magical. Venice is unique in the world. While there are plenty of museums/ galleries the city itself is the real star. The winding paths and canals and inevitable dead ends with their own surprises make it the most explorable city in the world.
We a heading back to Italy for ten days this Spring and will in fact spend three days in Venice. Enjoy your trip. Pat

No theory about why I don't think Siena is such an outstanding hill town: It's full of tourist "sheep" and it's gotten to the point that it's almost a Disney-fied version of an Italian hill town. English is widely spoken in Siena and that makes it comfortable, I guess. Besides which, there's a certain "cachet" in bleating a professed love for Siena. Of course, this is only my opinion and my impression. Personally, I find Perugia fascinating compared to Siena.
My vote remains with Florence :-)

To clarify my love for the small towns ... I like the change of pace they give you from the "big three". Plus Siena is a good base for visiting surrounding small cities. With only 6 days though, the extra day may be better spent in one of the big cities. If you had 2 weeks, then I'd say add it to Siena.

VENICE ALL THE WAY!!!! We spent 3 days in Venice and couldn't get enough of it. If I could live there I would. Florence??? Blech!!! That was our least favorite place in out whole European trip. Siena is just like Venice without the canals. I love the water so Venice is amazing!!!

IMHO, three nights still aren't enough for Venice but for a flying visit, two nights should do - to get a feel for the city, see the main sights - and plan to return :) I'm one of those who loves Siena but I did spend an extended period of time there once ... It's actually not that small a town, so maybe that confounds people's expectations. It gets crowded, feels cosmopolitan, is comfortable with tourists, and isn't as quiet as a visitor might expect a hill town to be. Still, it's worthwhile to spend a night or two in Siena just to hang out in the beautiful piazza del Campo in the evening with locals, tourists, foreign students, people of all ages. (It does quiet down a little in the evening.) I'd say, spend 2 nights in Siena simply because you'll only have half a day in Siena after you arrive from Orvieto.

The difference in taste between Florence & Sienna depends on the type of person you are. I'm in the love Sienna camp, although when I was growing up, I would have said Florence. I find the statement that Sienna is too full of tourist to be hysterically funny since the poster then suggested Florence would be better. Florence is a big city, with all the traffic, noise, dirt, and tourists that comes with a big city. That said, there are things to see in Florence that cannot be experienced anywhere else. But, since you've already been, I would advise Sienna. It's a much smaller town, and you can find small, hole-in-the-wall restaurants that you won't believe. It's quieter, it's redder, it has it's own feel. On the other hand, since you're from Arizona, Venice would be the most different from your home. At night, Venice is magical. Have you considered staying in Mestre for your last night? The airport isn't actually in Venice.