Originally Posted by ExplorerWannabe

So I have a family trip to Portugal next June and am looking for suggestions from folks who have done these legs. This will be my first (only?) year as a 1K and I'd like to use these lovely GPUs if possible but I have decades flying in Economy so am not too broken up over flying in E+ either. I'm more concerned with earning PQM than RDMs.

I need to be in Lisbon on Jun 9 so could fly out Jun 8 or 7 going through Dulles or Newark. I really hate Newark but EWR-LIS is a 767-400ER versus 757-200 on IAD-LIS. The return from Lisbon would be Jun 30 or even Jul 1. I have a side trip to the Azores but it seems like the best thing there would be to book separately since I am heading over from Porto (OPO) and returning to LIS to catch the flight home. It would be really nice to combine the itinerary so I could just check my bags through from TER and just have my carryon for the overnight in LIS but that's not worth the premium UA seems to want to charge me -- or do you think a UA agent could work the same way Expedia or Google Flights seems to? The other complication is that while I'd like to try to get an upgrade for the UA legs, I'm willing to pay the roughly $200 extra for J/I fare to/from the Azores.