You really have to plan this in 15 minutes increments every day. What do you want to do and see, the figure times those things will occur, and add in the logistics for getting to lodging and airplanes. Your new schedule is still a jumble.

Figure out Maui vs Big Island and choose one. The Big Island has a volcano erupting now, but intermittently, like 20% of the time. Is it a priority to gamble seeing this? I say this because 3 nights in Hilo is otherwise not a good use of limited time. Hilo is the second largest city in Hawaii and has a very large homeless population. I liked the South Pacific vibe of Hilo, reminded me of cities in Fiji. I have recently visited New York and Chicago with lots of walking and transit use and never felt unsafe. I did not feel safe walking around in Hilo in the middle of the day, homeless outnumbered locals and tourists in the center of downtown by about 4:1, I was walking to buy bread at a supermarket. And there are beautiful beaches all around the Big Island but I never saw one swimable, all had too many rocks under the surface to safely enter and be in the water.

Looking at flights home, maybe choosing Delta makes sense multi city flying home from either Maui or Kona via LA, or a OneWorld ticket from the same cities flying home via Seattle. Just throwing these ideas out in case syncing up with the HNL nonstop is eating up too much connection time.

3 islands in less than 2 weeks is a mistake that can’t be ameliorated by tweaking, so pick 2.

Being negative again, but Aloha Spirit? I’ve been to 49 states and Hawaii ranks near the bottom in friendliness. 2 road rage incidents and handmade basically “tourist go home” signs all over Maui do not jibe with Aloha spirit. The best thing about Hawaii is the weather, much better than the Caribbean, then the scenery and beaches (but not Big Island).

Sorry but your plan leaves you almost no time to see/do anything As you've discovered there are no 'red eyes' from the East Coast to HI (as there are none from Europe to the US) since you are flying westwards and the time zones just don't work for an overnight flight. So first day completely shot and likely some jet lag for at least some of you. So potentially 2nd day shot as well. To get 2 days in a place requires 3 nights so if you want 2 full days on Oahu means 3 nights. Then flying to Maui and wanting 3 days there (4 nights) your entire 7 days is now used up. Pick ONE island since at best you have five full days plus a few jet lagged hours. Don't jump from island to island or you'; spend more time in airports than seeing/doing anything.

The latest plan is so crazy I really don't know what to say ?!?! but I'm going to take a try

Leaving 21/23 = two days which includes your very long flight, then checking into a hotel somewhere, using public transportation not renting a car, and going to Pearl Harbor, then back to the airport for your next flight. So a hotel for 2 nights here? In Waikiki? Go back to airport, take flight.
24/25 Maui = get a rental car/get a hotel. You don't have time for Road to Hana. Haleakala is a don't miss but with less than 48 hours not sure how much you can fit in regardless of how interesting. Go back to airport, take flight.
26/28 Island of Hawaii = again for 48 hours, get a rental car, get a hotel, sleep two nights, return to airport, take flight.
29 HNL - are you going to stay at the airport arriving from BI? Or try to fit something in that last day, or maybe is an over night? Or the same day from Big Island to HNL for your flight home?

aloha & happy planning!! suze

Thanks all. Appreciate you taking the time to share and throw in ideas. grateful!
will keep posted after trip on how this goes..

Anything specific with packing? We are vegetarians ( No fish no eggs no meat and no alcohol )
The next time we plan, I'll do better homework. This is a much deserved trip for the children and I hope it all goes smooth and they get some rest and refresher.

Thanks again!

Is it advisable to take laptops and leave in the room through the day? airbnb/vrbo stays...

I travel with a laptop. I leave it in my hotel room. I have never had a problem. But I have never stayed at an AirBnB or VRBO in Hawaii.

I pack the same for Hawaii as I would for the Caribbean or Mexico tropical vacation/summer clothes- sneakers, sandals, swimsuits, cover-ups, shorts, tshirts, a couple nicer things if you plan to go out to dinner, sunhat, sunglasses, etc.

Vegetarian food is typically pretty easy to find in Hawaii.

Have you looked into AirBnB's yet? I ask only because they work better for weekly stays (cleaning fees, etc.) and can be kind of expensive or not available when you are only going to be each place a few nights.

Yes Suze. booked vrbo in Maui and Hilo and hotel in HNL. pretty expensive but couldnt find hotels either, so had to book these.

The flight from Hilo lands @1:21PM in HNL. & the flight from HNL to BOS is scheduled for 3:30 PM .

Is it feasible ( given the airport layout, terminal & luggage pickup) for us to check in a luggage OR
should we avoid check-in?

The timings are pretty close. Google search says both airlines are in Terminal 2 .

Could someone with experience chime in please?
Thank you

Can you check any baggage from Hilo direct thru to BOS. That's what we have always done. Clearing agriculture and checking bags from departure airport. I don't follow the avoiding check in phrase. Are you flying Hawaiian? In the past few years we have been held on the tarmac on various flights waiting for a gate to open.