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!

I would just stay in Kauai longer. 2 days really isn't enough and you're going to lose almost a whole day changing islands. 3 islands in 9 days is a lot of moving around.

I agree with Mary that a third island would take time... but I have done it.

One option could be to spend two nights on the Hilo side of the island... that will cut down on car travel if you want to do the Falls, Mauna Kea or Volcano National Park.

Problem is no chain hotels on that side.....

I have done it too, not by choice though On a 9 day trip I had to go to Maui for 2 nights and it cut into Kauai & Waikiki by 1 night each, plus I wasted time and money going from HNL to OGG to LIH and back to HNL in those 9 days. Thankfully there are 2 OGG-LIH non-stops a day

We go to Hawaii all the time, so it really wasn't a big deal - we've seen all the sights and just go to hang out and relax. This sounds like it may be a trip that will also include sightseeing and other activities, and if that's the case, 3 islands is too much unless they don't plan on sitting still very much

Totally agree Mary... I am amazed at how much people try to fit in... especially on the Big Island when there is a tremendous amount of travel required. People tend to underestimate it ... and think that VNP is near Kona....

3 islands would be a waste - I've done it. Once.

I've been to Kaua'i and Hawai'i twice each, and IME, they deserve about equal time when trying to allocate days. So I'd absolutely spend the extra time on Kaua'i.

Thanks everyone, I extended my stay one more night at the Big Island and one more night in Kaua'i, really looking forward to the trip! 3 islands in one trip? What was I thinking???

I really loved Kaua'i the last time I visited, so I'm looking forward to revisiting a few places there again. Never been to the Big Island, definitely planning a day at VNP at the very least.

Arthurrs,

I truly believe that the Big Island is one of our hidden American treasures. Check out other threads on things to do there. Find a way to go up to Mauna Kea and the Observatories... especially if you can do the free Keck Observatory tours... love it... and then the star gazing in the evening.... Lots to do away from Kona.... and so memorable.

OK, now I want to go back!

Check out the Kauai restaurants thread too. There are several excellent ones on the south side that weren't there the last time you were on the island.

I agree.

Three islands is pushing it for a nine day trip. Figure you lose at least half a day every time you island hop, hopping to two additional islands, and you're going to lose a day just flying intra-Hawaii. That's not worth it for a trip that short, IMHO.

I hopped two islands in seven days and I wouldn't even do that again. Hawaii is supposed to be relaxing, not a mad rush to see as much as possible.

Visit Waimea Canyon and Hanalei, where The Descendants was filmed.

After a long day of travel yesterday, we're finally here on the big island, let the adventure begin!! Got a really nice room in the Makai tower with an awesome view! Thanks everyone for all the helpful advise! ^

And beyond Hanalei - to Ke'e Beach, the most beautiful on the island IMHO.