I should say up front that I am a member of the Grand Wailea Resort, so I get a discount when I stay there, and it substantially improves the ROI. I first stayed here in 1996, and then returned in 2012, and have since been back 4 times. The staff is unfailingly pleasant, helpful, and prompt. The bellman will remember you if you return. Great story: upon my first return in 2012, we sat at the lobby bar [beautiful setting], ordered drinks and started chatting with the bartender. It was about 4 in the afternoon, so he wasn't super-busy. After a couple of minutes, he says to me: "So, how long has it been since you were last here.....14-15 years?" Now, like any good psychic parlor trick, there are ways that could have been set up, but in the moment, it did not matter.
A few tips:
1. Rent a cabana, at least for one day. Pricey, but the sense of luxury is delightful.
2. Don't fail to try Amasia. Wonderful food.
3. Make sure to walk along the beachfront. The path can take you for miles along the island
4. You don't need a car to get to/from the GWR, but you will if you want to tour the island. Rental rates at the National desk at the GWR are actually very reasonable.
5. If you want to see the sunrise at Haleakala, plan to leave about 2am to make sure you get there without rushing.
6. This really is a great family hotel. You can let your [hopefully well-behaved] kids loose, and know they are reasonably safe. There is much for the to do, and kid-specific activities like Movie Night. When I first visited with my wife and 9-month-old, we had a great time.
7. Though it's not a quite, secluded romantic getaway, it's also a great place for couples blissfully in love, and for anyone who can let the minor annoyances of a resort roll off their back.
8. If this is your first time in Maui, you really cannot go wrong here.
Pros:
1. Beautiful grounds and buildings;
2. Excellent food at Amasia.
3. Wonderful breakfasts and the setting for breakfast is great.
4. Adult pool a welcome respite from all the kids, but not quite isolated enough. Service at the pool is pretty good.
5. Right next door is the Four Seasons, with a wonderful outdoor bar with live entertainment and excellent restaurants. And other locations are nearby as well. You can walk to a number of great places to eat.
6. Wailea.
7. Mau.
8. Hawaii.
Cons:
1. I am a coffee guy, and there is no nice way to put this, but the coffee at the GWR Officially Sux®. How this can be with so much good [not bland 10% Kon, but really good] coffee in Hawaii, and the resurgent Maui coffee industry, is just beyond me. When I am at the GWR, I simply walk over to the nearby Honolulu Coffee Company every morning. [BTW, I think the best coffee on the island is at the café at the Hanua Kai.]
2. The place is large, and the food apart from Amasia and breakfast is only average.
3. Adult pool regs are not rigorously enforced, and so there is often a smattering of wanna-be-adults. It's Hawaii. Relax.
4. Breakfast is popular. Go early. Sometimes, there are seams in which the line diminishes.
5. A place this large almost always has some renovation or repair, large or small, going on. Usually, it is not intrusive, but there are folks who don't like that.
6. It's a big hotel, and it is never empty. Lots of people here, and that often means wait times, leaving VMs and waiting for call backs, etc. Relax.
7. Standard rooms are not huge, but they are pleasant, and the bathrooms are very nice.