Hotel/B&B/VRBO Reservations

Why do you want to wait until the absolute latest? I would start looking now for the most choices.

I don't literally mean the latest date! I just want to make sure I'm covering all my bases. I also read on one of Ken's posts that some travelers were having trouble booking accomodations in the Cinque Terre (booking in March/April for September 2012).

You asked about "the absolute latest date" so I assumed that is what you meant. My advice still stands. If you know your destinations and dates you will have the most choices if you start looking and booking now.

I guess you're asking, "I have overnight stays in 8 different cities. Since I can't research them all and book them all simultaneously, which cities should I nail down first?" I'm not sure. But, I would focus on Venice and Rome first, since they're fixed as your arrival and departure cities, then work toward the middle. That way, if you were unable to get suitable accommodation in one city, you could shift your itinerary. Next, I'd work on any city that's a must-see for you, or where you had a specific place in mind to stay. Then, fill in the rest. Since you have a set itinerary, there's no advantage to waiting. You will have fewer choices in each price range the longer you wait, as the best places in each price get picked off first. In a big city like Rome or Venice, that's the real problem with waiting - not that you won't get a room, but that the one you do get will be poor value for money (including having to settle for one "worse" than you want, or pay more than you want for something you consider acceptable).

I'd recommend that as you find places you want to stay, double check the cancellation policy. If you have don't have to prepay or pay an actual deposit, reserve as you find lodging that you like. If you find something better later or rearrange your itinerary, you can contact the hotel and request to change your dates, or worst case, cancel. Just be sure keep documentation on the cancellations.

Now. Everywhere. Why would you try to guess the absolute latest and somebody slips in and grabs the one room you had your heart set on? I just don't get it. Maybe you are one of those sort of people who can know exactly when the stock market is exactly at its peak to sell and the exact date that the stock market is at its lowest to buy. I don't tend to risk missing the bus. You're more of a gambler than me.

I'm with Nigel and Karen on this one. I'll just add that while your trip is getting into low season, you don't know when there might be holidays that send the Italians and other Europeans flocking to resort and tourist areas. All Saints, in late October, is one I know of. In many European countries schools are closed for a week, and parents grab the kids and go. Also, lots of retirees have figured out that September and October are great times to travel. I'd do it now.

Thank you for all your replies; they have been most helpful. It is absolute insanity to try to book last minute as some of you have mentioned. I am currently trying to book a hotel in Venice for three days in mid-September and am having a bit of difficulty. Sadly, some of the places recommended by Rick are booked full! I will have to review other options (i.e. vrbo) and keep plugging ahead. If anyone has had any great experiences with apartments on vrbo for any of the places listed on my itinerary, please let me know.

Here is where we stayed in 2009. We like it there and it was a great location. You could look out your window and see the boats, etc. Residenza A Tribute To Music
Riva Schiavoni 4127, 30122 Venice

I like to use Trip Advisor to find hotels. Then I contact the hotel directly. If they do not require a deposit and do allow cancellations, I make the reservation. If they do require a deposit, I check Booking.com or some other booking website. These sites generally require no deposits, and you can cancel with no fees, until very close to your arrival day.

If I were you I would book now. September reservations book up pretty fast. I guess I don't understand why you would wait. If you agenda is set than do the research and book before your choices become very limited. Venice and especially CT could book up pretty quick in Sept. It is a nice trip you have planned. But it is really hard to find nice hotels or apartments in all the places you are going. So do the research and book early to lock in. It is alot of work and time passes quickly.

I booked my upcoming trip using mostly hotels.com. All I booked were fully refundable until at least a few weeks before. I have switched my itinerary around a bit and that's fine because I am not locked in.

I booked Venice 6 month ago and found some full then.
In going to Europe every summer, we do our research of places to stay and then contact the place directly. That way we get a good rate that goes to the owner, not a consolidator .When you book thru some agency and the place has a problem with your reservation, you will have to deal with the agency. When booking directly with the place, we have never had a problem that wasn't taken care of immediately. Happy travels.

Book now. We traveled to Italy last September. I thought 6 months prior to our departure was enough time. Could not get a reservation in our favorite b&b in Rome. As someone else noted, check the cancellation policy. Some may be quite liberal.