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I was just there a few months ago. Stayed right nearby in Kapalua.
First of all the beaches are great. None of the rocky crowded mess you have in Honolulu/Waikiki.
Going up Haleakala and seeing the crater is something you'll rarely see in your lifetime. Amazing views, interesting drive.
Did Road to Hana once a quarter way through but got sick from all the twists and turns and went back, couldn't stand it. But there were some fun coves along the way with waterfalls n shit.
Whaler's Village in Kaanapali is where the shopping and dining is. Restaurants are pretty mediocre in my opinion but overall that's a fun area to stay because it's more vibrant/busy. There's a nice walkway along the beach that stretches quite long. The rest of the island is extremely quiet. Pro tip: the Lululemon store in Whaler's village will imprint a logo of the Hawaiian islands for like $10 on any purchase. I got a pair of shorts with this and it's a very memorable item.
Lahaina downtown is honestly a little crappy. It's just a gigantic tourist trap in my opinion. There's a lot of mom and pop seafood restaurants if that's your thing. Otherwise I've never cared for that area.
I'm not the most outdoorsy type so other peoples' suggestions on hiking and sightseeing will be better. After a couple trips to Maui I've found that Oahu definitely fits my vibe better. I like being in Honolulu, way more to do for folks like me.
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