Stay:
When traveling to Hawaii, we usually go to Maui since Dallas has direct flights. I think the Four Seasons Maui is my favorite. It is a casual, well-kept property with friendly staff. It's also right next door to the Grand Wailea. We have actually stayed at both during the same trip, so the kids could play at their massive pool situation. I love the orchid lei and kukui nut necklaces they give everyone at check-in. The Grand Wailea has a fun luau night. The performers are really great, but I try not to look at the whole roasting pig. Grand Wailea also has an amazing collection of nine Fernando Botero bronze cast sculptures throughout its open-air lobby.
See & Do:
We swam with tons of sea turtles and paddle boarded right outside of the aforementioned hotels. Taking a boat out snorkeling was fun too. Don't forget to pack cover swim leggings and swim ts. My husband got stung by a jellyfish on his arm and wished he had on protection. Leggings are also great sun protection for your backside while snorkeling. Sunscreen gets wiped off from sitting or isn't applied high enough under the bathing suit seam = a burned bum. Oxybenzone, the most common ingredient in chemical sunscreens, is being banned in Hawaii by 2020 due to its toxic effects on ocean life (can't be good for your skin).
I highly recommend chartering a helicopter through Blue Hawaiian to see all the amazing waterfalls around the island. You can get right up near them; it's amazing. We had an awesome female pilot. My son felt a bit ill from the unique motion of the helicopter. They sell motion medication and bands in the Blue Hawaiian lobby. I would have given those to him before we went out if I had known that basically anyone that ever feels motion sickness at all will probably feel motion sickness on a helicopter ride.
Shop:
An open-air mall called The Shops at Wailea is walking distance from the hotels. Prada, Louis Vuitton, Tiffany & Co and Gucci have stores there, and Gucci offers a 20% at this particular store due to its proximity to Asia. I bought new collection luggage and bags when I was there. I bet the other stores offer the same discount, but I didn't check. Worth a trip!