We are trying to go to Italy Sept. 21 to Oct. 1 or Oct. 26 to Nov. 5. Which date is likely to have the cheapest tickets and when would be the best time to buy them? I know that no one has a crystal ball, but any opinions would be very much appreciated. Which of those date spans would be best for seeing Venice and Florence and how soon do we need to get rooms? Thanks everyone!

I bought my this same time last year for Sept 16 - Sept 25 and they were about $900 from Indy to Rome....

We flew back on a Sunday and that could have been part of the reason for the higher price.

Rooms is Rome are plentlyful. I recommend Roman and Italian B&B in Rome, had no problems getting a room there. Venice and Florece, can't help you there, going Sept 2007.

I think the weather would be much better the earlier time frame. But I think prices may be slightly cheaper the latter time frame. One thing to consider, when is daylight savings over in Italy? An extra hour of daylight might be a good thing.

Do a search on here for rooms in each of the cities and see what appeals to you. You might also want to check other websites like tripadvisor.com. When you've picked something that looks good, repost here to see if Fodorites have feedback.

With respect to your posting question, there is only the Europe board. You highlight Italy when posting so if someone does a search it will help bring up this post.

I would love to hear the magic answer to this question, too!

We are going from Oct 8-20 ish... and I don't know whether to buy the tickets now or wait for a sale that may or may not happen.

For you, I would guess the later time would be better price wise. Though you may hit some rainy/cooler weather. Of course that's another gamble!

I already have our rooms booked based mostly on advice from this board. If you are thinking of going the earlier week, I'd suggest booking soon - well, only if it is important to get your top choices. You can wait a bit and still definitely find rooms avail, too.

I would advise not to wait, I've been watching prices and it looks like they are only increasing for the Sept-October time frame. We just bit the bullet and bought our tickets last week and prices have gone up over $300/person since then....hope this helps!

As others have said, the weather is better (warmer, that is) during the earlier dates, while the prices are probably cheaper during the latter.
If it were me, I'd spend the extra money and go the earlier time.

Later dates you're likely to get 'aqua alta' in Venice. OK if you don't mind walking across duckboards in Piazza San marco or don't mind wet feet!
Personally I prefer out of season, particularly in Venice which is most atmospheric on colder, misty days. Less tourists in all the galleries & churches too!

Thanks to everyone! I hadn't even thought about daylight savings time which falls in the middle of the later time period. Still, even with that and the Venice high water possiblity, we will probably go then because of ticket prices. This board is invaluable!