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Hawaii Advice - Family Trip (11, 9, 2). Thanksgiving 2027
Posted on 3/31/26 at 3:59 pm
Posted on 3/31/26 at 3:59 pm
Yes, a bit pre-mature, but I wanted to get some feelers. I've always been anti-Hawaii because I would rather spend the same or less money and go to Costa Rica, Mexico, Europe, etc.
We do a family trip every third Thanksgiving. Wife and I + the kids. Kids will be ages 11, 9, and 2. We've gotten into a good routine with the older ones, so the baby will be a wild card.
Goal will of course be beach, pools with activities for kids, and some day trip excursions for the kids as well.
We will probably do Saturday-Saturday including Thanskgiving Day. I have had the 1 Hotel Hanalei Bay bookmarked for years and would love to do that, but not sure it makes sense with the kids.
I've got about 750,000 Hilton points bank rolled as well.
Any Hawaii aficionados here?
We do a family trip every third Thanksgiving. Wife and I + the kids. Kids will be ages 11, 9, and 2. We've gotten into a good routine with the older ones, so the baby will be a wild card.
Goal will of course be beach, pools with activities for kids, and some day trip excursions for the kids as well.
We will probably do Saturday-Saturday including Thanskgiving Day. I have had the 1 Hotel Hanalei Bay bookmarked for years and would love to do that, but not sure it makes sense with the kids.
I've got about 750,000 Hilton points bank rolled as well.
Any Hawaii aficionados here?
5
Posted on 3/31/26 at 4:23 pm to LSUShock
My wife and I took grandkids in the age range of your kids to the Big Island several years ago. We’ve taken them to several great places but Hawaii was by far their favorite. My wife says Kauai is her favorite island so I think your family will love it.
Posted on 3/31/26 at 7:21 pm to LSUShock
If you want to use Hilton points, I suggest these Hilton resorts.
Hilton Waikoloa Village on the Big Island or Grand Wailea on Maui
Hilton Waikoloa Village on the Big Island or Grand Wailea on Maui
Posted on 3/31/26 at 7:56 pm to LSUShock
Pools can be great. But the beaches aren’t Florida beaches.
Lots of cool hiking, golf, food scene shuts down around 8:30 so prepare to eat early.
Lots of cool hiking, golf, food scene shuts down around 8:30 so prepare to eat early.
Posted on 4/1/26 at 12:09 pm to tigerfoot
We just got back from Oahu, now officially seeing all islands. We have a 13 yr old. For your trip I would suggest maybe Maui, the beaches are great, lots to do, great resorts. Big Island would be my next suggestion. We actually really liked it. Not sure about resorts there, we did some awesome Airbnb, one by volcano, and another on leeward side in private subdivision which was great because we had a nice pool we had access to, plus it gave us access to a private beach area that was really great. If you stick with these two islands you'll have a great time.
Posted on 4/1/26 at 1:34 pm to Shotgun Willie
Hilton cards have increased bonuses right now so if you want to take a look at those now would be the time to do so
Posted on 4/2/26 at 12:01 pm to LSUShock
Cruise Hawaii on Norwegian Cruise lines Pride of America cruise ship. In the one week you will visit the four main islands. Plenty of daily port time as ship travels in evenings. Fly in/out of Honolulu for the Sat-Sat cruise.
Posted on 4/2/26 at 12:46 pm to LSUShock
Family did it a few years back, it was much cheaper to fly back on Thanksgiving day vs the Friday/Saturday. Left Hawaii Thursday night, landed in Houston Friday morning.
Posted on 4/3/26 at 8:16 am to TigerintheNO
Damn, you are not wrong. Just looking at this year, it's $400-700 cheaper depending on the airline. Great callout.
Posted on 4/3/26 at 9:37 am to Maniac979
quote:
f you want to use Hilton points, I suggest these Hilton resorts.
Hilton Waikoloa Village on the Big Island or Grand Wailea on Maui
I stayed at Grand Wailea (Waldorf) this past fall and it was great. While I didn't use points, my brother did without any issues.
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