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Don't forget about Red Hill, we leave via scooters from black sand beach and go all the way to little beach and back. It's amazing
 
If you haven't gone out with Lahaina Divers to do the Carthaginian at dusk, and the Mala Pier at night, do that. I had a whole mess of dives at Mala before I went out on the boat, but it is like a totally different universe at night. The huge conger eels are out actively hunting (and they're impressive), and the sponge crabs are crawling. We even found a seahorse! I thought I had pretty much done Maui, but that was a great new experience.
 
I was the one that went with Greg from Maui Scooter Diver's and going to Maliko Gulch was awesome. To give some perspective, it is just up from Mama's Fish House and Paia on the Hana Highway. Far off the beaten path and well worth the trip to have an entire dive site to yourself. I have dove all over the world and never have I seen so many turtles in one spot. My video doesn't do the dive justice. There was also lots of structure that we scootered (sp) through during this dive. The water was very calm in the morning, and with the scooters you cover what would normally take multiple dives and long swims to accomplish. Greg dives often and will get you in the best location based on swells and conditions. Just remember, no snorkel the scooters move too fast.
 
Call Greg at Maui Scooter Divers. Although he mostly does south Maui diving, he also goes to the leeward side of the island for some cool dives. It would involve a drive (obviously), but perhaps would be worth it to you.

I highly recommend Maui Scooter Dives if you are looking to do something different. Coolest thing I've ever done underwater! Well worth the drive from Kaanapali.
 
Was it worth it? I've heard stories of people seeing about half a hammerhead, at a distance, the entire trip.

Done this trip twice...first time (during the Winter) saw zero and decided it was a myth. Retried last summer and saw five, a couple up close. Season matters and you have a better chance during the summer months. Not sure where October stands but this is one of those trips that if you hit it on a good day you will see more than hammerheads. Either way it is a nice drift dive and I enjoyed it.

My other boat dive recommendation will be for the Molokini Backwall which I also did with Lahaina Divers.

There are a lot of shore diving too very close where you are staying. Obviously staying in Kaanapali, you have the obvious popular choice for Black Rock but my top recommendation for a beach dive is Mala Pier. An excellent spot with lots of white tip sharks, spotted rays, and turtles. If I would do one dive in Maui, I think Mala Pier will be it.
 
Do the Lahaina Divers trip across to Molokai and dive with the hammerhead sharks. Pricey but very much worth it! We are 2 for 2 seeing hammerheads fairly up close on this dive. It is hovever definitely an advanced dive- current, depth, and on occasion, pitchy surface conditions.

DivemasterDennis
 
https://www.shearwater.com/products/swift/

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