Trip for OH's 30th - can you help me with the options?

I am thinking about planning a trip for Mr W’s 30th in late September 2015 (he is still 28 at the minute…), probably at the end of September/beginning of October or slightly later in October. As we already have 2 week-long trips booked next year together (Grenada and Chicago), and he has another one with his family to NYC (I shan’t be joining them, it’s for the best, really), trying to convince him to take yet another trip later in the year has been be a little difficult (despite the “me going away with family doesn’t affect our trips” claims). But it is a special birthday (and I’d be very happy to treat him to it, mainly because I will want to get away again), I’m mulling over options. By the time Oct/Nov comes round (i.e. 11 months before the planned trip thereby permitting me to buy tickets), I’ll have 60k/70k FC miles again, so at least I can get us to fly out in UC should I be able to track down the Gs! 8D
So I’ve come up with the below list as potential candidates, and would very much appreciate some help from all the lovely and well-travelled v-flyers to help me decide!
Hong Kong – I think end of Sept/early Oct, or even later in Oct would be a good time of year to visit, and as our first trip, maybe 5-7 days would work well. This might be a good option as I’ve never been too fussed to visit (don’t get me wrong, I’d be happy to go, but as I’m from that part of the world originally it feels somewhat less exotic to me), so it would be an extra nice gesture that the trip is more about him and his birthday :p I think the G availability isn’t too bad on this route, but I could be wrong.
Boston/Cape Cod/bits of New England – again I think it’s a good time of year, with the beautiful autumn colours, and at the tail end of the whale watching season (not a requirement as have seen them before, but would be a nice to have). A little road trip though so would probably require at least 1.5 weeks for this one. The actual flights though would seem a bit short to go in UC, so this could be a better destination when my PE vouchers come through (my membership year won’t end until next July v( ).
West Coast road trip – I’ve fancied this one for a while. Fly into SFO then drive down to LA and then to Vegas, Grand Canyon, before flying back from LAS. Again I believe it’s a really good time to do, but this one would probably require 2 weeks! Gs are likely to be hard to come by… n(
Vancouver/Seattle – Not sure whether it will be a little chilly then (I quite like some warmth but as long as it’s not freezing, I’ll be ok), but this might be a one-weeker? I understand the Gs are easier to find on this route? Relatively?
Lisbon/somewhere in Europe – a bit less exotic (and more importantly, non-VS route!), which is why it’s at the bottom of the list. Europe I think we can go to at any time, so might be a bit less fancy for a big birthday?
Any insight would be much appreciated! I'm not sure how the costs would compare either (hotels etc, rather than the flights mainly). Also any other suggestions for late Sept/Oct would be very welcome, too.
I’m always super impressed by what you experienced travellers have to say y)
So I’ve come up with the below list as potential candidates, and would very much appreciate some help from all the lovely and well-travelled v-flyers to help me decide!
Hong Kong – I think end of Sept/early Oct, or even later in Oct would be a good time of year to visit, and as our first trip, maybe 5-7 days would work well. This might be a good option as I’ve never been too fussed to visit (don’t get me wrong, I’d be happy to go, but as I’m from that part of the world originally it feels somewhat less exotic to me), so it would be an extra nice gesture that the trip is more about him and his birthday :p I think the G availability isn’t too bad on this route, but I could be wrong.
Boston/Cape Cod/bits of New England – again I think it’s a good time of year, with the beautiful autumn colours, and at the tail end of the whale watching season (not a requirement as have seen them before, but would be a nice to have). A little road trip though so would probably require at least 1.5 weeks for this one. The actual flights though would seem a bit short to go in UC, so this could be a better destination when my PE vouchers come through (my membership year won’t end until next July v( ).
West Coast road trip – I’ve fancied this one for a while. Fly into SFO then drive down to LA and then to Vegas, Grand Canyon, before flying back from LAS. Again I believe it’s a really good time to do, but this one would probably require 2 weeks! Gs are likely to be hard to come by… n(
Vancouver/Seattle – Not sure whether it will be a little chilly then (I quite like some warmth but as long as it’s not freezing, I’ll be ok), but this might be a one-weeker? I understand the Gs are easier to find on this route? Relatively?
Lisbon/somewhere in Europe – a bit less exotic (and more importantly, non-VS route!), which is why it’s at the bottom of the list. Europe I think we can go to at any time, so might be a bit less fancy for a big birthday?
Any insight would be much appreciated! I'm not sure how the costs would compare either (hotels etc, rather than the flights mainly). Also any other suggestions for late Sept/Oct would be very welcome, too.
I’m always super impressed by what you experienced travellers have to say y)