I know many may advise not to, but I could save more than $1,000 if I prepay my hotels for my three-week trip to Italy from Sept-Oct.

What are the prevailing thoughts on this?

The biggest savings: prepaying my stay in Sorrento would save me about $400.

I can't think of any reason I would NOT go on the trip.

Do you have travel insurance that covers unexpected cancellations? If so, I would book in advance if it really makes you save that much money,

I would just make sure that these are reputable places. Check trip advisor and other sites for any complaints, places that were not as decribed/advertised, etc...I would only pre-pay with a credit card.

Email the hotel after you have pre payed your rooms to verify your reservations.

Also print email & take with you. I used Otel,com in Nov. for reservations

in Florence & all went well with great savings.

cdispoto, I have pre-paid my hotel in Sorrento for early October. I have trip insurance which covers me for the loss if for some reason we can't go on the trip.

I agree with the comments above, do all of those things and get good trip insurance.

I pre-paid hotels in 2009 in Venice, Siena, and Rome...directly through the hotel. It did save money and there were no problems....like denisea said, be sure they are reputable & that other travelers have given them good recommendations. I emailed back and forth several times first.

"I can't think of any reason I would NOT go on the trip."

It's usually the UNEXPECTED that causes people to cancel their trip. But, as pointed out already, if you've got trip insurance, then go for it.

You only save $1,000 if the currency ratios remain pretty much what they are right now. Obviously, the euro could go up against your currency (and you look like a genius), but considering recent economic news that seems unlikely to me. What if the euro goes way down?

What is the per-day savings in each place? From your comment, it sounds like Sorrento is the highest, but then how much is really saved (versus the risk) in the other places?

It's not all or nothing. If the Sorrento offer is too tempting, then I would pre-pay that but perhaps not pre-pay some/all of the others.

Before I pre-pay a hotel I always make sure that it is refundable within a certain amount of time. I pre-paid in Sorrento as you did but I have a 14 day cancellation fee for a full refund. Be careful that you know the cancellation policy. Good luck!