Advice with flights from Jackson, MS to Hawaii
 

Traveling with my family late July to Hawaii, and haven't been in the airline "game" (especially leisure with a family of 4) in a while. Would appreciate advice on the main flights, as I plan on flying into HNL and out of KOA. Am I missing any considerations?

(Will post later - and continue my research - on things to do/island, inter-island flights and places to stay, although I plan on maximizing the use of my Hilton points on the Big Island and Kauai.)

Thinking of:

Flying JAN-HNL on a Thursday
- 2 nights Oahu
- inter-island flights TBD
- 5 nights Kauai
- 10 nights Kona (Waikiloa)
Returning KON-JAN Fri/Sat.

I don't have any airline miles to speak of, but am leaning towards AA (fare dependent) since I have lifetime Gold, which at a minimum would possibly help in boarding and checked baggage fees.

thanks!

Looks like you have a nice trip planned. Without knowing your goals related to your destination choices, it is hard to comment any further.

You don't say if your itinerary is set, but ten days on the Big Island seems too much, and two days on Oahu not enough. Also, why are you not going to Maui?

My .02 would be 4 nights Oahu, 5 nights Kauai and 7-8 nights on the B.I. Our fav island is Maui, FWIW.

Thanks - we're pretty laid back, looking for beaches and relaxation, some hikes/drives, snorkling and maybe a scuba excursion would be nice.

Thanks for the responses! We generally prefer to go one place for a long time (2 weeks in Ireland) instead of something like 7 countries in 10 days sort-of-thing, but in this case are willing to make a few short hops.

Thanks - we're pretty laid back, looking for beaches and relaxation, some hikes/drives, snorkling and maybe a scuba excursion would be nice.

Big Island... we've been there before for 7 nights (sans kids) and enjoyed it. We like the idea of staying at one place for a longer time, and alternating between relaxation and leaving the resort. Also trying to maximize our Hilton points and save on hotels (big factor), which means staying 5 nights at a time (10 in this case.) Maui doesn't have any (affordable) Hilton's, so we thought we'd save it for another trip, but based on advice we might revisit that thought. Also done Oahu before, and figured 2 days for Waikiki was enough, unless we venture to the north shore or something like that.

Thanks! See above for why we're doing 10 nights on B.I.... right now unsure what all we'd do on Oahu for 4 nights (not necessarily into nightlife, shopping and crowds?) but we'll revisit Maui, and see if we want to swing a hotel for a bit.

Grand Wailea on Maui currently showing five nights standard reward available various dates in late July.
95,000 points per night with fifth night free = 76,000 per night

Thanks for the data... we'll be scrimping by to get what we have planned... wish I had an extra 380k!