Maui was a beautiful island that made for a great trip. It provided endless options for relaxing, exploring, and really enjoying ourselves. It’s really impossible to explain how beautiful this island is and how it’s part of the United States—not Bali or French Polynesia, etc. I would have to say that the number-one thing we did was the bike ride down the volcano, hands down. At 10,000 feet, standing over a crater larger than most islands, you have the chance to just soak it all in while watching the most incredible sunrise. Mind you, this is along with other people who are equally floored and appreciative of the opportunity they have just been given. It was an incredible experience (although I was as nervous as you can get the entire way down). It is something I will remember doing my entire life and look back fondly on.
For something more touristy and less adventurous, the luau was fun and something I think you should do while in Hawaii. Many of the hotels we found try to sell you on their luau and the convenience of it because it’s at your hotel, etc., but I say to spend the money, make the drive (if necessary), and go to the Old Lahaina luau. It’s by far the best on the island, with an extensive buffet, great show, super staff, and perfectly kept grounds.
If you should find yourself in Maui on Halloween, watch out. It is basically their Mardi Gras (like in New Orleans)—a lot of very drunk people in costumes—but the party stays in Lahaina. If this interests you, there are shuttle buses to get you there that your concierge will know about, and they will require you to make a reservation and pay in renting a car is a must, especially if you are the type who likes to leave the resort, see things/places, or drive the road to Hana, etc. Note that in Maui, you pay per driver when renting a car. My husband always drives, but we usually put both our names on the contract. This was a big mistake in Maui, as they charged us extra and I didn't drive once.
Regardless of where you stay, venture to the other side of the island. All the beaches in Hawaii are public—even those behind the hotels. That said, nothing is stopping you from exploring other hotels, common areas, etc. Toward the beach, behind the Four Seasons in Wailea (where we stayed), there is a nice path that connects to several other hotels. It’s a nice walk and affords you the opportunity to see other hotels. We had lunch one day at the Fairmount Kea Lani (built to try to replicate Santorini) and enjoyed ourselves and the meal very much. If you are looking for a good family hotel, I would suggest either the Westin (pictures attached) or the Grand Wailea. Both offer tons of pools, slides, waterfalls, and kids’ activities. Wailea is about a half-hour from the airport and considered the more expensive side of the island, with lots of beautiful landscaping, fountains, statues, and upscale resorts. There is also a high-end outdoor shopping mall in Wailea called the Shops at Wailea—a lot like Rodeo Drive, but Hawaiian-style.
Lahaina has more action and people, and I would say it’s considered the more fun part of town. There are lots of restaurants in close proximity and a place where people just walk the streets (Front Street mainly) and hang out (like Newport, RI). There are several beautiful scenic overlooks in Lahaina (as well as the best luau on the island) and several art galleries.
I have mixed feelings about the road to Hana. Some people will tell you it’s a must-do, and others will say you waste an entire day driving, borderline getting sick, all to see what you can basically see everywhere in Hawaii (incredible beaches, water, sand, etc). If you have a strong stomach and some extra time, I would say this might be something to consider. There are gorgeous views of the coast, several hundred curves, and lots of waterfalls. The roads are very narrow, so the person who is driving really needs to pay attention—maybe you can switch off driving?! There are places to stop, swim, take pictures, and relax, especially if you find yourself carsick.
Although we were there in the fall, winter is a great time of year to be in Hawaii. Winter (November-March) is the peak whale-watching season. It is also the peak travel season, so you will pay more and find things are more crowded, as well. Because whale-watching is such a big attraction there, it is highly competitive, and your excursion choices are unlimited, but pricey. Bring binoculars! Food can get very pricey here, as well, but you do have a few options to cut back. Many times when we travel, we have our mini-bar emptied and go to a local grocery store to get the basics to get us through at least breakfast and some daily snacks. Maui is no different, and grocery stores are in abundance. If you are looking to cut back a little, do it on breakfast and/or snacks, because the lunch and dinner options here are too good to pass up.
If you’d like to see something a little different, drive past Wailea to the southernmost part of Maui. There are lava fields there from the most recent volcanic eruption (about 200 years ago). Most concierges will not mention this because just past the lava fields are some other, more quaint beaches. These beaches have incredible water and have a lot of "privately run" water-activity rentals, meaning they don’t get a cut, so they don’t tell you about it. We fell into it, to be honest, and it was beautiful. Old folklore says not to take lava rocks off the island—it’s bad luck.