I have read this site for many trips and finally signed up (this is my first post)...thanks!

As a Hilton Honors Diamond Member, I am planning a surprise trip for my wife who is turning 30 in August. We are very active and love to explore.

I can either stay at the Grand Wailea for 3 nights (Ocean View King) for 217k points or The Waikoloa Village for 4 nights (King Lanai Deluxe Ocean View) for 172k points.

We do not have kids, we are looking for a quick romantic get-away and my wife has never been to Hawaii. So my questions are:

It looks like the GW is much better, but...
Is the GW worth the extra 45k points and one less night?
Does the GW upgrade Diamond members (like the Hilton's so awesomely do?)
Overall which place would be best for someone who has never been to Hawaii and is the GW worth it for one less night.

We are flying from Cali, so it is not that bad of a flight.

Thanks so much for any feedback you have.
Greg