You've mentioned you want to fly Rome, but you haven't mentioned where you'd be flying from.

AA flies to Rome (and it's within the season where all its flights to Rome are still happenenng). And you have enough miles to do what is needed there, and not necesarily anywhere else. And you have the miles already at the airline, so you can use them "instantly" if/when seats become available.

And since AA flies it own planes to Rome, assuming AA provides service from your statring airport, you can check availabliity of outright awards seats online.

However, you'll need a thrid-party service (such as ExpertFlyer, a paid service, www.expertflyer.com) to check upgrade availability (without actually calling).

You also need to think about whether you absolutely need to be on the same plane, in case each flight only has 1 award seat.

You also need to figure out how certain these dates are. Because to an upgrade (or outright award) with most certainty, you want to be ready to book 330ish days out (as soon as AA puts the flight into the system). On some flights, awards can be available from day one, but once those disappear, they may never reappear.

AA allows you to book one-way awards, so for yourself that may make sense, since you can book each direction (a week apart), as it becomes available, if it becomes available at 330ish days out.

The paid fare your husband is reimbursed for, he'll have to "float" for almost a year (because he preusmably won't be reimbursed until he actullay flies, but for best chance of upgrade, assuming he has no status with AA), he needs to buy ticket the moment ExpertFlyer shows that an upgrade is available.

(Note: Upgrades and awards come out of the same bucket. So if you find out at the same moment that one upgrade and one business award is available at the same time, the moment you book one the other may disappear. Which is why you wnat to understand this process completely before it's 330ish days before Sep 8, ie by early October of this year.)

Be awrae that you'll have to pay about $700 in co-pays to upgrade one ticket with miles. That co-pay is separately billed (when the upgrade goes through), so chances are he won't get reimbursed for that part. For you, if both options exist, it comes down to 100k for doing it all with miles or cash cost plus 50k plus $700 co-pay for doing it as an upgrade. You have to decide if saving 50k miles for later is worth the cash cost of the trip plus an extra $700 miles.

Please note: You can only upgrade on AA metal. So for your husband to upgrade, he has to fly AA all the way. For your outright award, if you can't get a second seat on the same plane, you might be able to get it on another routing (involving AA partners), but for that you'll have to call. (And if it's not avialable that day you call, you'll have to keep calling back.) Only AA's own metal awards are searchable / bookable online at aa.com. You can try to search award inventory on partners through various means, which you'll have to research, between now and October, but it's a bit tricky and not 100% reliable always (it may involve, for example, setting up accounts at certian other Oneworld airilnes).


If you decide yoo do want to go the AA way, you can ask the moderators to move this thread to the AA forum. (You're not allowed to post the question again in that forum, which is why the moderators would have to move it.)

(The reason I think it's probably AA specific is because you don't have enough points in Sapphire for both an upgrade for yout husand and an award for you at any other airline. Whatever the ariline, per person, you'll need about 50k miles for upgrade both directions and/or about 100k miles for outright award both direcitons. So Sapphire could only help if you decide each of you will fly a different airline, or both of you will try to upgrade from a more expensive fare at an airline Sapphire can transfer to, and will give up on using outright awards. But, as I said, you want the miles in the airline you're going to try to upgrade to at the instant you buy the tickets, and you want to try to buy tickets at the instant a third-party site tells you upgrades are confirmable.)

Or you can research the various aspects of what you need to learn and post in the appropriate thread (in the appropriate airline forum, AA of whichever) for each specific question.