But would that business class ticket be worth $900 to you? Seems like it might not considering your priorities as mentioned upthread.

Look, who really cares if the ticket is 990$ cash. It's going to be domestic F and no one pays for that unless someone else is paying. You can just buy two tickets for 990$ in Y and it's a relatively easy day trip. Don't use that as a way to calculate a reasonable CPM.

I just looked at your dates, and the flight seems to be about $420 to STI and $490 to POP. Looking at the overall calendar it's safe to assume that you won't be paying any more than that, as basically all of the dates year-round are within that similar price range. If you wait, and judiciously check your dates on multiple search engines daily from now until August you will probably be able to get it in the 300's, as the DL non-stop to STI goes as low as $340 all throughout April. If you can afford to pay it, then I would pay it, instead of redeeming miles into airports that aren't preferred.

All of the proposed mileage redemption options are OK, not great, but for a Y redemption to an overpriced destination you can never really score a wonderful deal unless you want to fly Spirit (and then your GF will be pissed...). First, I think you need to look at what an AA redemption would look like, if it indeed becomes available at the rates you like. I'm based in BOS, and all of the potential 'low' awards to the Caribbean always have awful routings, and often an overnight in MIA. Your GF will not like this most likely - I know mine wouldn't. Plus, you are already putting down a lot of miles for flights which might not be so convenient to you.

I would 100% NOT redeem miles for airports which would prove inconvenient for me. It's expensive to buy the ticket, but not unreasonably expensive, and the redemption options seem to be weak into POP. I mean - if you can get AA/DL availability into STI only do it on the direct flight (or the overnight in SJU if the GF is interested), or else you will make your trip turn into a hassle. Otherwise I would only look at options into POP. I have no idea what it takes to get from STI to your resort, but I know my GF would hate me if I did that to save 50$.

You have lots of options. Before you consider STI, research it. Look at the distances involved, and consult the GF to see what her preference is. I would buy the tickets, since this is a vacation and would like for it to be as stress-free as possible. I often like to take my GF with me on a nice C/F redemption, and she will only let me route it through 100 countries on 8 different carriers if there is something rewarding at the other end, and it is as stress-free as possible. I'm sure yours is the same way (although I could be wrong and she could love planes and airports.....).

I would just buy the tickets (in a few months) and save the miles for a time when they could be better used. I don't necessarily mean this in terms of CPM, but in this case preferred routings and schedules.

Good Luck!

Right, I was just stating the price to make it known that that's what I was using to calculate the CPM using the formula you provided earlier. But you're right, if my only concern is to get from A to B with little care for business class then $990 would be quite the overvalue.

I'll definitely consider this. This will be the first trip with the gf so it would be nice to make it a stress free one. I would discuss it with her but I was planning on it being a surprise - the great reveal being in the airport itself. She just came back from volunteering in DR for a week so I figured a week at a resort in DR would go over well as a surprise. Very much appreciate the input and thanks for factoring in the gf variable.

I agree, save the points and buy tickets. $485 isn't a whole lot for the distance you are flying, and the flight options are so much better. Even if you got low level awards on AA, most likely it would be an overnight flight. That can be good or bad, depending on your own preference.

I also surprised my wife two years ago with a trip to the Riviera Maya. Basically told her that I planned a surprise trip, and to block off the dates I had booked. I also got 3 other couples to go along with us, which made the surprise that much better. The morning of, I told her where we were going (Secrets Maroma Beach in Mexico), and gave her the hotel brochure which got her super excited. Then in line at SFO she saw one of the other couples and got even more excited. On our layover in DFW, we stopped at a bar where we met the 3rd couple and she was going crazy now with excitement. 4th couple met up with us after customs in Mexico (they arrived just before we did). She was blown away!

Funniest part was the first two days at the resort, she couldn't stop looking around trying to spot the other friends who might randomly show up!

Buy the tickets and make it a smooth trip. Save the points and miles for next year when you've built up a few more, and spend them on a nice international business class award for the two of you to Europe or Southeast Asia.

Ha! Excellent story. This is our first trip together so I thought it'd be nice if it's just the two of us but perhaps I can implement your intermittent couples strategy in the future. Thanks for the tips.

Have you thought about JetBlue? You can transfer Amex MR directly to JetBlue instantly. They have multiple direct flights from JFK to STI all day.
Just ran a sample search Aug 7-14 and got:
Airfare (in points)
30,900

Taxes & Fees
$97.10


Granted, that flight in cash would probably only be $340-$450. If you don't have $800 to book 2 tickets, then burning the miles is your best use in my opinion. If you have the cash, then it's a really low redemption value, but they're your miles so use them your way.

Didn't even consider Jet Blue, let alone realize they were a transfer partner of Amex MR. I also found JFK to my preferred airport POP for 35,500 + $97.10. I suppose this is another option to consider. Thanks for the heads up!

You might try milewise.com, sometimes they can help present solutions that might otherwise be missed.

I used milewise when I first started searching for award tickets for this trip but at that point I wasn't an Amex MR member and I was only searching the programs that I was a part of. Oddly enough though, I just did a search JFK-STI and it's not listing JetBlue as a transfer option from Amex MR nor is listing JetBlue as a cash option. However, it is listing it for JFK-POP. Either way, for now on I'll be sure to search all programs rather than just the programs I'm a part of.

Usually the amount of options for award flights for people like us with miles in lots of programs is a little overwhelming - but that's a good problem