We are going to Maui in September for a 10-day, no-kids, fruity-drink, tuna feast. (There will also be many hours on the beach.) I've been to Hawaii about 15 times and, as evidenced by 15 trips in the ten or so years I've had disposable income, I love The Great State of Hawaii.
I have been to Maui most often (I've also been to Kauai and Oahu) and I get asked pretty frequently what to do on Maui, what restaurants are the best on Maui, where's the best place to stay on Maui, etc etc. So, instead of looking for this email every time someone asks, I figured I'd just POST this damn thing so Google will lead people where they need to go.
Where to Stay
We stay in Wailea, at Pineapple Inn, in the Cottage. It's $215/night for a two-bedroom cottage with a full kitchen and this is a SCREAMING deal. We have stayed at Pineapple five or six times and I LOVE IT. I like it more than a resort. In fact, I do not even want to stay at a resort in Wailea. I will only stay at Pineapple.
It's small: just the cottage (a guest house type building) and 4 other double-occupancy rooms. They have snorkel gear, umbrellas, beach mats, coolers, etc for the beach and the owners could not possibly be more awesome, cool, hospitable, and fantastic. There is a laundry, plenty of parking, no daily resort fees, nobody to tip, no $19 drinks. They have a saltwater pool and hot tub and since the property is so small, I can only remember ONE TIME I had to share the pool space with someone I was not related to. It feels like MY house and MY pool (in Maui!). It's so awesome and private and such a great value.
I could probably write 500 additional words about Pineapple Inn, but I will restrain myself. LOVE LOVE LOVE.
There is a Costco right by the airport and we usually fly in around lunch, hit Costco for supplies (beer, sandwichy stuff, snacks, bottled water for the beach) then go to Pineapple to check in. (A beer upon arrival is pretty much an absolute necessity after an 8-hour flight from Texas. DON'T FORGET TO BUY BEER.) They also have leis, for a good price, if you are feeling like you need one immediately upon arrival.
There are a LOT of fancy restaurants in Wailea, but we tend to prefer places NOT in a hotel. So, this list skews that direction.
This is where we got married and the food was pretty okay last time we were there (not THE BEST, but still yummy) but what I really like is the view. The view is very awesome. The ownership has changed since we got married, but it's pretty similar food. Plus, since this IS where we got married it feels like a must-visit to us for that reason alone. If you were not into doing dinner here, cocktails and appetizers would absolutely be lovely and you'd get the same view. This is a Bev Gannon restaurant.
Literally ON THE BEACH and for this place you DEFINITELY want a sunset reservation. I'd call before you arrive on the island, several weeks in advance if you can. Sometimes, we can see whales from our table. Every time we leave I am so HAPPY and PLEASED with my evening. As I recall their wine list is a little pricey (goes with the territory, perhaps) but they have some nice wines by the glass. Really good food, really nice view, spectacular service.
Sansei, Kihei location
It's in a strip mall, so sunset reservations do not apply. BEST SUSHI EVER. When we go to Maui I try to eat here twice. Three times if I can talk Chris into it. I'd make a reservation for early in your stay and then if you want to go again you'll have time. Get the panko crusted tuna special for sure (maybe TWO orders of it). Oh, wait, I found a picture!
Panko crusted ahi with arugula and spinach in a soy butter sauce! DELICIOUS!
The tea duck eggs rolls are also to die for. I could make a whole meal out of those.
They have a very extensive cooked/hot menu for those in your party not into raw fish, plus lots of (DELICIOUS) sushi and tons of sake and Japanese beer. It is awesome and it's always packed and you aboslutely need a reservation so you don't have to wait two hours for a table. I could eat here every single damn night and still be asking Chris if he wanted to go again at lunch.
Tommy Bahama's, Shops at Wailea
This is in a shopping center and there's no view. The food is pricey for what it is (Welcome to Maui!). I'll be super honest, this is not my favorite place because the atmosphere is pretty formulaic and the service is just kind of casual for how expensive it is. BUT. They have great cocktails. If you need a place for a big, froofy, wild cocktail with a wedge of pineapple? And you are staying at the above B&B and thusly have no hotel or pool bar? This is a pleasant place to consume such a beverage and have a snack and then go buy postcards at the ABC downstairs.
Somtimes, they have live music. If you don't have a reservation for dinner the girls up front are all snotty like they work at some AMAZING restaurant and I always want to kick them because HI YOU WORK AT A LICENSED CLOTHING RESTAURANT. Just get a reservation so you don't end up kicking a seventeen-year-old girl.
This is a simple place but they make a great breakfast and the service is always so friendly. Banana Macadamia Nut Pancakes are my favorite and the coffee is good too. Here, look at this mocha. It is probably a 1,000-calorie mocha, but vacations are made for 1,000-calorie mochas, yes?
Things To Do
It's the on back side of the volcano in Haleakala National Park, past Hana. Very cool hike that we REALLY enjoyed to a couple of waterfalls. It's not too strenuous and it's gorgeous. There is even a bamboo forest, which is kind of fun to walk through.
The National Park Service says,
"Visitors can hike the 4-mile (round trip) Pipiwai trail following the stream which courses through the `Ohe`o Gulch and ends at the 400-ft Waimoku Falls."
Charles Lindbergh's grave is out that way too, which is neat if you are an aviation nerd like I am.
It's a big, all day drive out there, though. When we go to Hana (and we've only been once but are going back on our upcoming trip) we spend the night because really, IT IS FAR AWAY and for us it's just too much to go out there, do things and then go all the way back to Wailea in one day. It's gorgeous though. Beyond comparison to any place I've ever been.
This is nice, but there are usually several tour busses. Easy enough to get to, but honestly not my favorite stop. Kind of MEH. Not a lot to see and it's fogged in pretty frequently.
The Pineapple Winery
There is a pineapple winery on the far side of the volcano and it's terrible and far away and crowded with stupid tourists that wax poetically about PINEAPPLE WINE FTLOG and....I would not go there if I were you. It's a day-killer for not much payoff.
If you ignore me and decide that you simply must experience pineapple wine before you die (?!), pack a picnic lunch. There's not a lot to eat out that way and they have some lovely grounds and picnic tables that you could spend some time at (while drinking pineapple wine baaaaaaarf).
Catamaran Sails (Sunset, Whale-Watching, Snorkeling)
I like the cats with Sailing Maui.
We have used them three times and their ships are AMAZING. We've done both the sunset sail and day-trip snorkel sail to Kapalua. Catered lunch, big enough boat for everyone, goes fast, see turtles, sunbathe, have cocktails, etc etc. I love this activity.
The cat picks up at the beach in Kaanapali, across from Duke's. What you do is you book the sunset sail a day or so in advance (check the weather to make sure it's decent), go to Duke's and have a lava flow at the bar, watch the catamaran come in, people watch, enjoy the atmosphere, and then walk out to the beach and onto the boat. Afterwards, you can have dinner at any place in Kaanapali (I like Leilani's, Duke's and Roy's [which is a little up the highway, but good, although you CAN find them on the mainland].)
This way, if you're staying in Wailea you can make a sort of afternoon/evening out of the trip up to Kaanapali.
I like to stroll the Shops at Wailea and the shops in Kaanapali at Whaler's Village. (I do not like shopping in Lahaina on Front Street. It's very trinkety-junky and I actually dislike Lahaina a lot.) Shopping is basically what I do when it's too rainy to go to the beach. It usually only rains for a morning or afternoon, then clears up and shopping for aloha dresses or postcards is an easy way to fritter some time.
I am super MEH on Molokini. It's a sunken crater and that's all sexy sounding and everything but it's SO CROWDED out there. Easily 15 or 30 boats at a time, 10 snorkelers per. The boats are smallish, it's not fun to ride on them like a catamaran is. You have to cross a channel with a strong current (BUMPY) to get there and....MEH. There ARE a lot of fish at Molokini, but there are a lot of fish where the Sailing Maui people took us and it was just a waaaaaay nicer experience.
Haleakala National Park
This is the volcano and I LOVE the drive up there. It takes a while, but not nearly as long as the drive to Hana. It's a pretty drive, with lots of places to stop. Maybe pack a picnic lunch. There's a lavender farm half-way up and I'd like to visit it this time. Once you get to the top, it's COLD and WINDY and so alien and so very cool.
You can see all the way to the Big Island - that's Mauna Kea and Mauna Loa behind Chris.
This is the crater - so cool right? Can you believe this is on a tropical island??
We've never done a hike on Haleakala, but there are lots of trails and we might try one this time. I have never done sunrise on the volcano but I am told it is also MEH because you drive up in the dark! And you can't see anything! And you have to leave at like 3 am! And, well, that sounds not very fun on a lot of different metrics.
The draw to this crazy idea is sometimes, as the sun comes over the horizon there is a green flash. Something about the curvature of the earth and the altitude, I think? But, only SOMETIMES. How mad would you be to go through all that effort and NO GREEN FLASH?
You can do a bike ride down the volcano, where they take you up in a van with the bikes and let you loose at the top to coast down, which sounds SO fun to me, but Chris thinks it's dangerous (I CANNOT IMAGINE WHY) so I can never talk him into it.
This is the beach we go to. In my experience, it is usually about this crowded. I have no desire to try other beaches because we have done that a few times and they just aren't as good.
There's a tiny public parking lot and you walk a little bit to the beach. It's smallish. There are a lot of turtles in the bay (I think they call it Turtle Town) and there are sometimes boats from Molokini that stop by. I'm told that the snorkeling is good, but I've never tried it here. I love this beach. It's super close to Pineapple, super accessible, and hardly ever jammed with people.
So, there you go. Two thousand words of opinion about what to see and do on Maui. (I am not known for brevity on this topic.) If anyone else has favorites, pipe up in the comment box. I'm always looking for new stuff to try!