can't help with the flights, though what you say about round trip v open-jaw makes sense. I would definitely look to book flights before you book anything else.

after that, I have found that looking about 6 months in advance is about right - September 2012 should be early enough to get the good prices, but not so early that they haven't started to book for that period. if there's anywhere that's a "must" you might enquire earlier of course, but be prepared for them to ask you to come back later.

Hello caze,

I can't advise on flights but you have come to the right forum. Some posters will be able to help you for sure.

I would first do all of your research regarding accomodation. Once you determine which hotels/b+bs in which you would like to stay, I would book them by September. Just make sure that the bookings are fully flexible (ie, you may cancel with no penalty - some have this within 3 days, some a week, etc.).

I think that it may be easier to find less expensive places in the country so even if you have to spend a little more in, say, Rome, for a good location it will even out.

First determine which areas you want to stay and then post back asking for specific recommendations. You will find a lot of recs for Rome and Venice by doing some searches on the Italy board.

Even if you don't book flights until later, start fare alert right now and get daily or at least weekly updates from sites like kayak.com to all potential airports and for different time period. It gives you charts of the actual price trend (not just guesses based on some mathematical models.) This way, when it come time to buy tickets, you have some empirical data to compare where in price swing cycle you are trying to buy tickets.

We too are going next April/May. I am going to get airline tix as soon as the April dates show up on the airline's web site. Then I will book rooms/apartments. We are flying open jaw as well but into Rome and out of Venice (US Air doesn't fly direct from Venice to Phil until May thus we are leaving from Venice at the end of the trip). With respect to booking, there may be better fares later on but I say 'a bird in the hand...'

carolsc

We are going to France next year and have already booked an apartment in Paris for the beginning and end of the trip and a house rental for a montb in Provence. We booked early because we knew where we wanted to stay and still couldn't even get the exact apartments we wanted. Maybe renting apartments is different than renting a hotel. Will start looking for flights in a couple of months. I like the Kayak idea- will do that immediately.

I would book in Jan.

There are several US airlines that fly nonstop from the US into Venice,Milan and Rome so would check on those for an easier trip over and back.Are you close to Denver,Salt Lake City or another major hub?
When is Easter next year? Always good to know for when the crowds are abundant in Rome.April is definitely high season over there for Rome(alot of spring breakers) so would start thinking about what you want to see and do and start making reservations.

Book the flights first, they are sure to get on the expensive side the more you delay. Here are some Tuscany rental sites I know
http://www.tuscanyfinerentals.com/
http://www.cottagestocastles.com/villa-rentals-tuscany-italy.aspx
http://www.tuscanynow.com/
http://www.traveltuscany.net/
http://www.florencevillas.com/

Accommodation can be booked at any time as you will have a lot of choices but if you are focused on picking a Italy rental with modern facilities the sooner the better. At the most late it should be 3 months or at least 2 months in advance. Preferably try to book 6-8 months in advance as you seem to keep traveling a lot and need to book the right villa at the right place

If you are trying to use airline miles, I would book or at least investigate the flights first. I have United Mileage Plus and really had to work their system (with help from this forum) to figure out how to use the miles I had earned. A very frustrating experience, but ultimately successful!

We usually book flights about six months out. Look on individual airline websites, the kayak site, and also on discounters' sites. We have used www.vayama.com, www.cheapoair.com, and www.ebookers.com with success in finding incredibly low rates. Never -- yet -- had any problems with these discounters. We book hotels after we have our flight booked and use www.booking.com for most of our bookings. Of course, if you need to book a popular accommodation, you might need to reserve earlier; but be sure you understand cancellation rules.