First time vacationing to Hawaii.....suggestions please?

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I am going back to Kona (big island) with a diving teenager for the second time.
I would recommend Kona Diving Company for all dives including a two-tank manta dive.
I stay in condos I find through vrbo.com I stay out of Kailua to the south. takes a little more time to get in but its seems to be quieter.
Hike the volcanos, jet ski, luau, hang out on beach and boogie board, all things we do topside.
 
I suggest do not concentrate on diving. 1st time in Hawaii, with your family, there is just too much to see around. If you have, say, 2 weeks, pick up 2 islands, 1 week for each, and do maybe 2-4 dives on each one. I'd personally take Kauai with a hike along Na Pali and a single 2-tank boat dive, and BI with a couple of shore dives and the manta ray night dive.
 
Boat diving is a toss up IMO. Figure $85+/tank before gear. Maui has Molokini and possible hammerhead diving at Kahoolawe, which the BI can't match.

You may be confusing the hammerhead dive with Moloka'i, as access to Kaho'olawe is restricted due to the large amount of unexploded ordnance there. A few dive ops go to Moloka'i out of Lahaina harbor if conditions are favorable (the channel between Maui and Moloka'i can get pretty treacherous).

We usually pay $70-75/tank, but of course it depends on the charter, distance to sites etc. Most of the South Maui outfits charge $140 for a two-tank, which includes Molokini as the first dive usually. If you sail out of Lahaina to Molokini, it will cost more due to the distance.

Agree with your assessment of BI, though. We usually stay in North Kohala and use Kohala Divers. Since they are the only operator that far north, we always have the dive sites to ourselves.
 
Correct, I confused the two islands. $85+ includes tip. I've been wanting to try some of the Kohala boat dive sites. Shore access up there is pretty restricted. I've read there is some nice coral.
 
Correct, I confused the two islands. $85+ includes tip. I've been wanting to try some of the Kohala boat dive sites. Shore access up there is pretty restricted. I've read there is some nice coral.
Mahukona and Ke'ei beach parks are two excellent shore dives at the northern tip of Kohala.
 
Done Mahukona twice and Ke'ei once, also another beach park (L-something). Don't recall liking them much, but maybe haven't thoroughly checked them over. The stretch immediately north of town looks like there might once have been access in a couple of places, but roads down to the coast all seem to be blocked now. Haven't tackled any of the trails farther north with a suitable vehicle yet.
 
Done Mahukona twice and Ke'ei once, also another beach park (L-something). Don't recall liking them much, but maybe haven't thoroughly checked them over. The stretch immediately north of town looks like there might once have been access in a couple of places, but roads down to the coast all seem to be blocked now. Haven't tackled any of the trails farther north with a suitable vehicle yet.
Lapakahi? I've heard of diving there, but have my reservations to try. 1st, the surf is pretty strong and the entrance is over some boulders, so this is pretty much like South Point. Combined with relatively long hike from the parking lot, this may not be attractive for many potential divers. 2nd, the legality of diving there is questionable since swimming is not allowed, only snorkeling (which I did once).

I had same luck with dirt roads in Kohala as you.
 
A little guide for Maui I put together for a cousin of mine who wanted to visit:

Trip Advisor things to do:
Attractions-g29220-Activities-c45-oa90-Maui_Hawaii.html#TtD

My votes on things to see:

Scuba out of Kihei: I use Ed Robinsons - gtreat crew and captain - Francisco, Dave and Bird will take care of you.

Scuba out of Lahaina: Use Lahaina Divers and have them take you to scuba with the hammerheads. it's amazing.

Maui Bike Tour: Aloha Bike Tours on the Island of Maui

Old Lahaina Luau: Adults $99 + tax = $103.12 (I recommend NOT sitting traditional, hard on your back): http://www.oldlahainaluau.com/

Sunrise on Haleakala – do this before the bike tour, DRESS WARM – its COLD + WINDY!!!!!!

Road to Hana – be sure to do this – full day of fun! Swim @ Chings Pond (watch the jumpers) and The Three Bears

VERY nice beach near where you’re staying – Honolua-Mokuleia Marine Life Conservation district

Restaurants

Coconuts Fish Café: 1279 S Kihei Rd Kihei, HI 96753
http://coconutsfishcafe.com

Beach Bums: 300 Maalaea Rd #1M Wailuku, HI 96793. Beach Bums BBQ & Grill Maui Hawaii
Happy hr 3-6, Live music 5-8

Paia Fish Market: 100 Baldwin Ave Paia, Hi. Open 7 days a week, Lunch: 11am - 4:30pm, Dinner: 4:30pm - 9:30pm. (808) 579 8030. www.paiafishmarket.com... Casual GREAT meal! Blackened Ono Sandwich to die for!

Mama's Fish House... 799 Poho Pl Paia, HI 96779. (808) 579-8488. http://www.mamasfishhouse.com/...

Five Palms... 2960 S Kihei Rd Kihei Maui, HI 96753. 808-879-2607... http://5palmsrestaurant.com/about.html. Best breakfast and view (near Kihei Fish Market)...

Eskimo Candy... 2665 Wai Wai Place Kihei, HI 96753... 808-879-5686. Eskimo Candy Inc. Maui...

Cheeseburger in Paradise - Lahaina

Freds Tex Mex - Kihei

Ulupaakua Ranch Store Deli Or Maui Cattle Co burgers

Grandmas Coffee House

=========

I would reccommend staying in a VRBO in Kihei - far better than a hotel.

Also - buy the Maui Revealed guide book
 
It makes no sense to me to drive to Hana and not see the one and only Hawaiian Red Sand Beach.

Re Haleakala, I'd rather hike there in the park after the sunrise than bike down the road (which imho is touristish, cheesy, and a waste of time). Also, I've been told that watching the sunset from Haleakala is as spectacular as watching sunrise, but the place is not so crowded and you do not have to wake up at 3 am if you are staying in Lahaina. We watched the sunrise after staying the night in the camping, then found good spots to watch. Then the busloads of tourists arrived, some puking from motion sickness.
 
My son and I spent several hours hiking down in the cauldron. It was an unworldly experience. If it weren't for the Silverswords, we could have been on the moon. I would also suggest you not hurry your visit to this magical place, take your time, you may never get back
 

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