For my Southeast Asia trip, I met my sister in Bangkok as she had considerably more time to travel last summer than I did. She was planning on going to numerous places throughout the summer and had briefly mentioned to me the idea that she was going to buy a round-the-world cash ticket for many thousands of dollars. I told her to NOT buy anything before consulting with me, as I knew that she had a small stash of United miles that could be put to very good use given United’s generous award routing rules.
Here’s the list of places she wanted to go:
Awesome time with me in Southeast Asia starting in Hanoi and ending in Singapore
The bulk of this itinerary was booked as two awards:
1) USA to TLV (stopover) to BKK; (open jaw) DPS to USA for 65k United miles in coach (pre-deval)
2) SIN to HND; (open jaw) TPE to DPS for 30k United miles in coach (pre-deval)
One “trick” that I employed is that travel from North America to the Middle East (USA to TLV in this case) is more expensive than travel from North America to South Asia. BUT, you can transit the Middle East on the way to South Asia, and South Asia is a more powerful zone than the Middle East (terminology taken from TravelIsFree), which means that by making TLV the stopover on the way to BKK, I saved my sister miles. (One caveat to note is that you can’t transit the same airport more than once while going one direction of travel. In this case, the most convenient routing was through VIE to get to TLV from the US, as well as to fly through VIE again to get from TLV to BKK, but that’s a no-no, so I had to reroute her through IST on the way to TLV from the US so I could use VIE as a transit to get to BKK).
I didn’t completely “maximize” the awards, as she still has one stopover leftover in the second award. She could have done something like, SIN to HND (open jaw); ICN to TPE (stopover); TPE to DPS (implicit open jaw since you didn’t return to SIN) if she had wanted to also tack on a visit to Korea.
Even though United miles aren’t as good for premium cabin travel after the devaluation, coach prices haven’t risen too much, and the routing rules are still generous for roundtrip travel. By taking advantage of the one stopover and two open jaws, you can visit many more destinations. If you’re interested in more stuff like this, I strongly suggest you read the complete guide to United routing rules on Travel Is Free.