Booking Accomodations or Not?

I would say not practical. People are looking at the low Euro now, and even with the volcano looming, are making plans. I can't imagine a bigger nightmare than finding no room at the inn after a long flight.

IMHO you're heading for frustration and trouble. First of all you say you're going to the "hot spots" which means other people will be clamoring for the same rooms and occupancy rates are high. Second, even if vacancies exist you have to find them which means a lot of tromping around to get "sorry, completo" answers. I don't think that's the most valuable use of your time on vacation. So while it can be done, I would not recommend it.

Use a mix of planned and unplanned nights. Certainly you know where you will be the first few nights, book that. Plan out your stops and assess the room situation, Venice for example tends to be tight, book there, Florence, not so tight, maybe have a list of a half dozen checked out prospects, and call ahead as your schedule firms, for more out of the way venues, have your list and just show up. Leaving even a few nights unplanned between stops can add great flexibility.

Are you joking? Do you intend to spend all of your vacation time walking around town with luggage (or backpacks) in tow looking for a place to stay for the night? That's not my idea of good time management. Many accommodations don't have obvious signage out front, so you could walk right past a building containing several very nice and inexpensive B&Bs and not even know it. A lot of B&Bs also have very limited check-in hours/hours of operation. Plan ahead.

Obviously you are getting mixed messages so you will probably have to flip your own coin. As school teachers limited to summer travel we have always drifted along with min plans. We always reserve the first night or two and the last night. The first night or two because we don't want to deal with finding a room after a long flight and the last night because it may be critical to catching our flight the next day. You will need to be flexible and it helps to call a head a day or two and arrive early. But the local the TI has always found us a room. You can do it even at peak time.

With only two people you should have no trouble finding "somewhere" to sleep. Triples and quads are much more of a challenge. The question becomes do you want to spend time worrying about it or do you want to focus on other things when you arrive in a new place? My husband and I were having a similar discussion last night and the point we came to was that if there is a plan we will follow it. If there isn't one we might tend to let the details overwhelm us and water down our goals. We did this three years ago when we decided that it was "too hot" to go to Rome. We didn't have reservations in Rome which made it easy to delete. Of course it's always hot in Rome in summer but we missed out on it for a pretty flimsy reason. This time around we have booked much of the trip in advance. Hopefully we'll stick to it.

Thank you to all for replying with good information and personal insight. I realized from the start that it was a fairly subjective question. We all like to travel differently. We will heed some advise and book certain days; leaving the rest up to chance and circumstance.

Thanks again.