As a fellow PDXer that has been traveling to SXM since ’98, I feel your pain about trying to use Alaska miles to get there. What used to be a simple overnight flight through DFW has now turned into a 2-day cattle-run. For our last trip, we ended up with a combo of miles and purchases with three different airlines for the round-trip.

I ran into the same problem this year but ended up finding a 10 hr 20 minute red-eye PDX-CLT-SXM for just over $200 coach on US Airways (1st Class @$650). I could get us to MIA using miles but first class flights out of MIA were running $500+ and included a one-night layover. As you said, first-class MIA-SXM is not available with Alaska miles. However, it was available with AA miles but we did not have enough.

US Airways is not a partner with Alaska but we will be able to apply the earned miles to our AA accounts. Which is okay as we have decided to stop being loyal to Alaska and evened cancelled our Alaska credit cards. Why pay $75.00 a year if you can’t book flights? Don’t get me started about the decrease in benefits of Alaska’s credit card. Capitol One; no annual fee, no foreign exchange fee and cash back!