Finally, after almost 13 years, I'm taking my family back to visit Hawaii! What took us so long? Family issues primarily (taking care of elderly parents who have since passed), and waiting for the right moment when everything lined up financially and our busy schedules permitted it, and the startling realization that my youngest is off to university for his first year in the fall, and may be gone in subsequent summers for coop work terms. Plus the need to burn these points/miles before they are worthless the way airlines and hotels are headed these days. This is probably my last year as a Hilton Diamond. I've let my loyalty slide with everyone else.

Pulled the trigger yesterday when I discovered for saver first class seats open up on United next week, and was able to schedule a return 9 days later in coach. Used up all but 1000 UA miles! Very happy to finally burn those miles! Flying into Kona on the 8th, and flying out of Lihue on the 17th. I have just enough AA miles and Trueblue points to get us between the two islands, though it's tempting to buy those tickets considering how cheap they are and the close in fee for booking award tickets less than 21 days in advance.

Booked a really nice room at the Hilton Waikoloa Village July 8-13, and Kaua'i Marriott Resort July 15-17 using a bunch of points I've collected over the years with Hilton and Marriott. I have around 100K points left with Hilton, none with Marriott. But what to do in between? Hilton wants an extra 10,000 points on top of their "regular" inflated rate the five days prior for one more night July 14 at Waikoloa, don't really like playing their nonsensical game with points. I could pay for an extra night or two at Kaua'i Marriott resort (only have enough Marriott points for 2 "free" nights), but quite honestly I'm put off with Marriotts "extra adult charge" only because we're 4 adults now with our children grown up, and that's on top of the hundreds of dollars they would be getting from me for the room and resort fees. Crazy!

So what to do July 13-15? Extend the stay at Waikoloa with what points I have left with Hilton? add a couple paid nights at Kaua'i? Combo of the two? I did look at doing a quick 2 day stopover in Hilton Hawaiian Village between islands, but I'd rather have at least 3 days in Kaua'i to enjoy that island than to play Hilton's game with inflated points for a stay there.

Would love some advice!