Originally Posted by Rivka (Post 47429530)

We are planning a trip for October 2013. I have been doing tons of reading and have a pretty clear idea of what we want to do, but I don't have a very good sense of when and how to book.

Here are my questions:

1. Is there any reason not to go ahead and book a room now?Nope, none at all. We'll probably book our August 2014 trip when then 2014 prices come out this summer. That way we're sure to get the resort we want.

2. If we think that at some point we may want to do a package (because if they offer Free Dining our week, we'll need one), does it matter if we book it all now or if we just make a room-only reservation for now and order tickets later?
Almost every time I've booked, a better deal has come along and my travel agent has applied the discount to my reservation.

3. If we book a room or package and they offer a discount later, can we still get the discount? Or should we wait to make reservations until/if they offer a discount?
Book now, and apply the discount later.

4. Do you have to put down a deposit to book a room or a package? As someone else mentioned: for a package it's $200, for room only it's the price of one night's stay.

5. Is there any reason why we can't make ADRs at the 180-day mark and then cancel them later if free dining isn't offered after all?Absolutely make them at 180

Thanks to anyone who can help me out with these!