When to make reservations

For travel in September, I would probably start making hotel reservations in February or March, especially if there are certain places you're got your heart set on. September is a very popular month to travel to Italy.

Its actually October. We arrive in Venice on September 30.

I agree with Michael. Earlier is better for the best selection of places to stay. As for airline tickets, just keep your eyes open and when it seems like the right time buy them.

I'd book hotels as soon as possible as there's typically no reason to delay (it won't get any cheaper). Flights are a different story -- look for fare sales, and try the Bing flight application. It uses historical data to predict whether you should buy now or wait. It only works 3 months out, though, so if you see a good fare before then...

Good point about hotel rates not going down. In fact, you can often find good deals if you book way in advance, especially if you're willing to pre-pay nonrefundable.

I would wait to book a flight to make hotel reservations. Your dates may change depending on the fares.

Even though I was making reservations 6 months in advance, I could not get my first THREE choices in Venice for October travel. They were booked solid. If you've got your heart set on a hotel or on a particular "class" of room in that hotel, book early. If you are forced to change your dates due to your final flight choice, then you cancel the room. You are likely going to settle on your flights months in advance and the hotel will have someone snatch up your cancelled lodging, so don't worry that you are leaving the hotel high and dry.

What Marianne said. I booked my hostel in Rome three months ahead, as soon as I had decided to go, because it's a popular place and I had my heart set on it. Then when I knew I could stay there I booked the flight. The other two cities I'm visiting I only booked at one month out. They're less popular cities (Ferrara and Perugia) and choice of hotel/hostel was not as important to me (just as well, as I did not get first choice hotel in either city).

I had a very hard time finding availability for hotels in Rome for travel in November when I started planning my trip in June. Finding hotels in Venice was much much easier. November is considered to the off season and I'd imagine October is busier than November. You really should book hotels asap. Remember to check the cancellation policy, and if you're pre paying (which I don't advise you to do), check rates and the fine print of an insurance policy.

I second what Tina advises, wholeheartedly. Too many things can go wrong to prepay for a discount with the terms of "no cancellation, no change, no refund" unless you've got an excellent insurance policy and all of your reservations for hotels are in accordance with the terms of the policy.