I am planning my honeymoon and looking to plan the best trip possible while maximizing the miles my fiancé and I have earned on United. We both have 167k miles. I believe I have a basic understanding of United’s 1 stopover and 2 open jaw allowance on multi-region award tickets but this has become a bit too confusing for me to handle on my own and calling United’s International booking line was no help.

Here are the some of the basic details:

We will be flying out of Boston and will be staying exactly 7 nights at a resort in the Maldives in January 2015 so we will need to get to Male somehow. Our original thought was to fly from Boston directly (with layovers) to Male and then attempt a stopover in Europe or Asia on the way back for another week. Through searches, I noted that there are 4 natural routings from BOS-MLE including Zurich, Vienna, Munich, and Istanbul. First off, am I correct in assuming those are the only stopover options? The United rep told me I would not be able to stopover in Asia on this itinerary. Does anyone know if a stopover in other Asian regions is possible given this itinerary? After many hours of trying different dates and city combinations, I found a few options for routings that would actually let me book them. The following itinerary is business class from BOS-MLE and Economy MLE-BOS, costing 122,500 miles total.

BOS-> MLE (destination)
BOS-IST (Business class I)
IST-VIE (Business class I)
VIE-MLE (Economy X)

MLE->VIE (stopover) (Economy X)

VIE-> BOS
VIE-ZRH (Economy X)
ZRH-BOS (Economy X)

I now know I can book this on certain dates. My question is are there other options? If I understand United’s open-jaws rules correctly, then the open-jaw can only be made at the origin or destination (turnaround points). Thus, we wouldn't have that option unless we booked another flight from Male to somewhere in the Central Asia region (none immediately appealing to me) and then booked a return flight from that location to Boston. (Does the open-jaw have to be within the same region?) Is there any way to have Male not be the final destination? I couldn't fly from Male to Vienna and then open jaw to fly from Prague or Munich back to Boston, correct?

Finally, I’ve read about tacking on a one-way flight to the end of your trip. This can be done “for free” using the stopover feature. My understanding is that if I use the routing above, I will have used my one stopover and thus I would not be able to add on a free one way to this itinerary. If I were to open-jaw from Male and return from a different city in Asia without stopping in Europe, I would still have my stopover to use for the free 1-way correct?

Anyone have better luck calling a certain United number when planning these trips?

Sorry for the long post, I asked a lot here... just looking for some (any) insight because I’d like to wrap up these plans in the next couple of weeks. Thank you!!