Luxury Hotels - Hilton Diamond Member Grand Wailea or Waikoloa Village

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

Are you referring to the Hilton Waikoloa Village Hotel on the Big Island of Hawaii....located within the Waikoloa Beach Resort??
I would definitely opt for the Grand Wailea....hands down....no hesitation.
The Hilton on the Big Island is a Zoo IMO....packed with kids, cold pools, overpriced dining with mediocre offerings.It's the only place I know of that requires you to pay an additional $50 for an oceanside table at their upscale KPC restaurant. That is just one example of their pricing structure....
The property is so huge...it can be over 30 min walk to your room...depending where in the resort they place you. Don't forget your sunglasses in the room! The parking lot is a great distance away from the lobby...and is over run with feral cats waiting to be fed.
The Resort is currently undergoing a pretty significant renovation at present and the disruption is more than mere inconvenience.
Many folks are not fans of the captive dolphin program that is featured at the resort.

Hilton Waikoloa Village is obscene.

The Grand Wailea is certainly several steps up from the Waikoloa Village. More compact footprint, more luxurious rooms, better facilities(including a great spa) and less family oriented. As long as you're celebrating why not splurge and pay for the fourth night on Maui? It would certainly be worth it IMHO.