Any suggestions on using points to get miles and hotel nights simultaneously?
My wife and I plan on taking a trip to Rome for our 20th Anniversary next year. We'd like to use Marriott Rewards Points (MRPs) to get United Airline Miles and at the same time, book a Marriott Hotel for the time we spend in Rome. We know this is possible, but we're looking for any tips, pitfalls, or anything else to help us make this work. It will likely be complex due to the availability of hotels on points, and the availability and class of airline miles reward travel, each of which may not sync up perfectly. United doesn't let you book more than 337 days out, but I expect I'll need to jump on it immediately to ensure we are able to get business class (since it's a special occasion). This will likely make availability even more challenging. We have enough MRPs to get a package we've heard about - 120K United Miles, and 5 nights in the Category 8 Hotel Gran Flora. Our desire is to spend 3 days or so in Rome either before or after our cruise which we booked using Marriott Vacation Club Destinations points. Therefore, we can be a little flexible in when we arrive and depart Rome, but we have a hard date for the 7 day cruise- 9/25/13 - 10/2/13). I have enough airline miles already for one ticket, and will use these MRPs to get the other.
I've done a lot of research on the airline's site, but would like to know about others' experiences in booking this type of trip.