Weather is more pleasant Nov-March, mostly in the low 80's I think. Summer is quite hot in places like Kihei, Maui, on the leeward (desert) side of the island.
I agree completely that winter is the time to be there for whale-watching.
We always went out with Pacific Whale Foundation, well occasionally with Trilogy, but always from Maui. Seeing the humpbacks is a highlight for locals and tourists.
If you go to Maui you need to see the Maui Ocean Center, great aquarium showing local sea life.

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If you go to Maui you need to see the Maui Ocean Center, great aquarium showing local sea life.

Absolutely.

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Originally posted by 92fstech:

Thanks again...more good info! Our annual schedule is pretty flexible, so we will shoot to go in the winter. Seeing whale activity like you described would be a real treat, and I'm all for avoiding the crowds. How cold does it get during that Nov-March window?

80 usually. Year round, well the time I avoid like the plague (beyond summer/Christmas when kids out of school) is October. That’s real humid that time of year. Winter is excellent. 70-80 peak, and I don’t know temp at night, but very light windbreaker type cold. So 60 on the lowest end? Nothing I would worry about. When I go now, I take 3 board shorts, including the pair I have on while traveling. 3 tees, and flip-flops. If I’m going to do any hiking 1 pair of tennis shoes. And if I’m going to Haleakala or if you going to Maunakea on Big Island you want some mild winter gear packed as it can get cold. Big Island gets snow up top, Maui, never in all my trips. Maui I pack a sweatshirt and some Adidas track pants to go to Haleakala. But honestly, Hawaii = being in the water as much as possible and skipping tourist shit. That salt water is as clean as it gets, especially if you find spots away from tourists and their stupid Coppertone. Due to all the reefs you want to only use reef safe sunscreen. During Covid the water was so nice because no Coppertone in the damn water!

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Originally posted by gjgalligan:

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Originally posted by 911Boss:
, sunrise at Haleakala is pretty impressive.

.

Wear more then a tank top & shorts like I did.
A LOT more!
Cold up there.

Sunset was awesome ... and it is wicked cold and windy ! This was great advice

Also Hana and beyond circle the island. past Hana the roads have potholes in spots... no big deal.

on the far side its a desert ! really cool.

Do Hana and a 360 on Maui.. worth it

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Originally posted by 92fstech:

Has anybody ever camped in Hawaii?

Remembered your question and I’m on the phone with my weekly call to my fam. He said Grandmas would be ideal but honestly he said, any camping places (state/free stuff) are gonna have homeless and you might luck in and get some meth heads around. Partying, most definitely. He said this place is good and just stick to this place. Look at the price, not bad, and he vouched for it. Should be safe.

https://www.campolowalu.com/

Our daughter and son in law live on Maui (up country) so the wife and I go there three of four times per year. We always do a VRBO. Most all will have a washer and dryer which allows you to pack really light. We go out to eat two or three times but the rest of the time we cook at the condo. We also make lunches for day excursions. It saves a fair amount of money. If you're going for a one time special occasion this strategy may not suit your needs.