The below recs are solid. I’ll approach from lunch. Tin Roof, the pool restaurant at the Andaz in Wailea and Mama’s are all great. When staying at Andaz, we ate lunch on campus several times. Paia Fish Market is very good. The original is all that’s left after the fire.
My favorite Maui restaurant was Fleetwood’s on Front Street. The food didn’t change my life but it was very good, the beer and wine excellent, music fun but not obtuse, and the service impeccable. A rooftop seat watching the sun set over the Pacific Ocean was about as close to Heaven as you can get.
We just went 2 yrs ago today..
Iao Valley was a short, but very accessible and awesome hike and one of the coolest places I've seen anywhere. We hiked up through the river a little and my kids swam in a rock pool. Not a hike but if you like waterfalls there's a good one maybe an hour into Road to Hana - you'll see jeeps parked on side of road and people jumping off a 12 ft or so waterfall. The Waihe’e Ridge Trail hike is pretty steep and has awesome views if skies are clear - but gets muddy and has almost no views if clouds close in.
We stayed in Wailea and tried to go snorkeling at a cove towards Makena 5 mins down the road. It was choppy with poor visibility and we left, and pretty sure someone was shark bait there last year. Makena Beach itself was really nice. Molokini was really cool - I'd advise taking one of the bigger boats to avoid chop on way back in.
Surfing is tough on Maui. There are beginner classes in Kaanapali but often little/no waves and some of the better breaks are pretty far offshore near Mama's fish house or up against rocks on the Kapalua side.
There's a food truck called Ono Tacos which burnt down in the fire but apparently reopened. The owner was incredibly nice on both of our visits, and tacos were legit.
If you're staying at Wailea Beach Club and aren't Marriott platinum try to get status ASAP (through credit card, etc) b/c the breakfast perks are really good at Whale's Tail.
Top Chef owns it. Good spot. MonkeyPod is also good. Kihei Cafe has a good breakfast but is cash only. The line moves pretty quick. 5 palms was also a good breakfast spot and had a good ahi Benedict. I never ate at Cafe Ole but heard good things. They ran the restaurant at the hotel we stay at and that was pretty good so thats another spot to consider. As mentioned if you can get into
Mama’s it is worth it.
Since you're staying near where I did last time.
- I took a flier and tried scuba last time vs snorkeling. Had a blast and saw an octopus. Maui Dreams Dive Co was great.
- Book Mama's Fish House now if you can, it fills up quickly. Monkeypod doesn't look like much but is an easy drive from the Wailea area. Maui Brewing company is fun too. Sadly all my other reccs burned down in Lahaina.
- If you fancy getting up early, do the sunrise bike down Haleakala.
to make reservations at Mama a couple months in advance and even then we ended up eating around 3 p.m. Food was great.
With Lahaina gone, I assume thing will be more crowded, so reservations in advance for most things probably advisable.
We stayed 2 nights at the Hana-Maui Resort, which is a Hyatt property. 2 years ago, it needed some work. The hotel restaurant is only open for breakfast. The Hana Ranch Restaurant across the street is very average.
The rooms are all cabins. Sunrise is around 6 a.m. and cabins are constructed so the sun shines in your window. It is stunning over the ocean.
We were able to beat most tourists to the 7 pools
As many know, I live on Maui, I have answers to each of your questions, and am happy to help.