Upgrade Premium Award?
 

I think I know the answer to this is a big fat no, but it's worth a shot. Is it possible to upgrade a premium coach award domestically with a VIP? I know you can do it on US (premium awards book into Y inventory and upgrade at time of booking for elites), but don't think so at AA. What's the scoop?

The idea is to book a ticket to somewhere in Hawaii the first week in July, pay for one and VIP it, then use miles for the second. Only issue is I'm a touch shy of the 150k for premium Hawaii Awards, hence the need for a work around.

You're talking about an AAnytime Award where you pay double the miles to avoid capacity controls? No automatic upgrade. No sticker upgrade. No mileage upgrade. Only possible upgrade would be the slight chance of a kiosk-offered upgrade. And I wouldn't count on that one. Rather than pay double for coach - have you called AA and tried to find a First Class Award? Sometimes, MileSAAver F awards are available even when MileSAAver coach awards are not.

I just took a quick look on EF for first week of July and found a fair amount of availability with MileageSAAver F awards to HNL from PHL (assuming that is where the OP is coming from) with connections in LAX or SFO. Its a little more inconvenient from PHL instead of being able to connect in DFW or ORD but it is still 763 service to HNL.

If I understand you correctly, you want to book one award ticket in F and one in Y, and upgrade the Y to F with a VIP? Won't work, can't upgrade the Y award ticket (except, possibly with a last-minute paid upgrade, $50/500 miles, if available (and generally not to Hawaii).

You could buy one Y seat (with dollars, not miles) and upgrade with a VIP.

More than just generally, Hawaii is specifically excluded from the program.

OOPS. I stand corrected. Didn't think it would have worked if possible, but now forget it totally. Buy ticket and upgrade, or buy miles and get two awards (or get credit card, or drive Lincoln, or....)

Drive to BWI, stay at Springhill Suites the night before on a Park and Fly rate that includes up to 3 weeks of parking. Purchase roundtrip YUPs to Hawaii for $1322.30 per person. Nice savings when compared to the 2527.62 YUP fare out of PHL.