I am planning a trip into Rome and out of Milan for late September 2012. I will either use Alaska Miles for a Delta or AA flight or United Miles for Lufthansa. Am I correct that you still start calling 331 days out?
And what are peoples experiences with Delta and AA mileage tickets to Europe.
Also, can I book the first leg and wait to book the 2nd leg when those dates open up later

Just snagged 2 AAdvantage Credit Cards spent $1k on each card

got 82000 miles booked RT US to Milan in April 40000 each

plus like $100pp tax so $50/leg otherwise free awesome deal

Might look into that AA has least miles across the pond for me

Personally would your return to come into 12mos time

and book a RT MXP Regional trains are cheap seat61.com always

save hundreds/FF miles I would not book it your way more $$

or FF miles. Happy Hunting!

The trouble with using Alaska miles is that you can't "mix and match" partners, so if you want to go to Milan you'd have to either use AA's nonstop from JFK OR go via British Airways via London (in which case you'd get whacked by BA's fuel surcharges, passed on to you gleefully by Alaska.) You couldn't take AA to London then BA to Milan on an Alaska award ticket. (Or, of course, since Alaska partners with Delta, Air France and KLM too, you could use one of those airlines - but only one - instead.) Also, Alaska only makes round-trip awards, so getting the return portion simultaneously with the outbound is more important, since you have no alternate carriers. In that case I'd wait until the return date is open for booking before making the outbound reservation.

It's a common mistake to assume that award seats become available right when the booking window opens (usually 11 months) and then are scarce afterwards. Actually, the opposite is more often the case: the airlines release seats into award inventory as the flight date gets closer, so that they have a better picture of sales and can make a better call on how many seats to release into award inventory. At the opening gun, they only have historic statistical records to go on, and the typical default position is to be conservative with releasing those seats too early. They'd rather sell them for money.

Sorry Quovadis but I disagree. I would definitely do the open jaw ticket where you fly into Rome and our of Milan instead of the hassles of trains,schedules,etc. Saves time and also the possiblity of trains being on strike which is a common thing in Italy anytime of the year.
Using mileage on an airline that goes in and out of LHR to get to Europe/continent is moronic with the unbelievably high departure tax out of that airport. The tax usually runs anywhere between $159 to 200 USD so that runs up your ticket even if it is a "freebie".Gatwick and Manchester are in a different category so LGW runs usually about $40 less on departure tax.
I fly for a US airline and do international flights and I can tell you that mileage tickets to Italy(particularly to FCO and VCE) are difficult unless you are going in January or early February. The flights are ALWAYS full! I am working a trip to Rome this week and we are full even on a Wednesday in October. Good luck!

We were fortunate to just book a trip to London from LA for next summer, July - August, during the Olympics, using frequent flyer miles on American. It was 25K per person, per segment, total 100K miles.

You can book very easily on AA.com.

Our mistake, and I pass on this advice to you: we thought that we had to wait 331 (or whatever it is) days in advance of our RETURN flight, whereas what we should have realized was that you can book your outbound flight one way when that date opens up for award booking, then book your return flight one way when that date opens for booking. That's how we wound up booking the trip in the end. We paid $5 in fees for the flight TO Europe and about $300 in fees total for the return flight.

Not bad! I'm excited! My only concern is that there are rumors flying in the media that American is on the verge of Chapter 11 bankruptcy... will our award tickets be honored? (I will search/start a seperate thread.)

Just booked two RT FC through United miles (usually use Delta) -- into and out of Milan, though have done open jaw in the past. We have to use two separate routes (SFO-OHare-Frankfurt-Milan for me, SFO-Seattle-Frankfurt-Milan for DH, and then a train ride! But the price is right.

Going in November, which made it easy. When I had to return to the US urgently from Rome last year I was able to snag a last minute FC ticket to SFO for 60k miles.

Usually going in peak or shoulder season with Delta miles I've had to have a travel agent work with the 331 days out.