If you want to spend most of your time on a hotel’s beach or at a hotel’s pool, I recommend the Wailea area rather than Kaanapali, which is more crowded and less relaxing, though better for long walks on an actual beach. The price differences are negligible. The Four Seasons Wailea is considered the best hotel on the island by experienced Maui tourists and if you factor in the square footage of the rooms and the lack of a “resort fee” tacked on, the price may actually be less than what other hotels charge. If you book through WhataHotel.com you’ll get a free room upgrade and an included buffet breakfast (about $100 for two people otherwise).
[We learned that the hotel bar is at its liveliest on Monday and Tuesday nights and that local women enjoy coming there to meet visitors, a mixture of corporate convention attendees and folks willing to pay $800 per night from their own pockets. We asked why locals would bother driving down from Lahaina, considering that Hawaii has a surplus of single men and is 9/50 when states are ranked by male:female ratio. “Women say that there are plenty of guys, but they want someone with more ambition and a better career,” was the answer. (What happens if the bar encounter turns into a pregnancy? About $72,000 per year in tax-free cash under Hawaii’s child support guidelines.)]
If you want to be on the go, I suggest staying in an off-the-beach hotel or condo near downtown Lahaina. If you can walk down to the marina there you’ll never be bored. You can use the money that you saved from not staying in a resort to take a submarine ride, a day trip to Lanai, a snorkel trip to Molokini, a whale watch, etc. You can enjoy the crazy huge banyan tree every day (planted only in 1873; one look at this tree and you’ll realize what awesome job security a landscaper has in Hawaii).
Staying in Wailea and want to snorkel around Molokini? Go through the surf to get on the Kai Kanani. Their sunrise trip is usually nearly empty so you can wait for a morning when the wind and waves seem light and then drive directly to the boat to hop on at 6:15 am. The nearest competitors will require you to drive in a car for about 30 minutes and then drive back down to where you started in the boat for about 30 minutes.
All of the helicopter tour operators are in a row at the main airport (follow signs for “heliport”) so maybe stop in and pick a tour after you get your rental car. I suggest going as early in the morning as possible and on a day when the winds are forecast to be calm. Wind+mountains = turbulence. It won’t be unsafe but it might be uncomfortable. Even if I weren’t a helicopter nerd I would suggest a helicopter as the best way to see Hawaii. A lot of the most beautiful areas are inaccessible by road.
Every local’s favorite burger joint: Cool Cat Cafe in Lahaina.
If you need to cover a wall with a tropical flower painting: Anna Keay.
If you love old maps and high-quality reproductions of old maps: Printsellers in Lahaina.
Note that Maui is not immune to the “vog” pollution coming out of the volcano on the Big Island. If you insist on blue skies and clean air, check the volcano activity level and consider booking on Kauai or Oahu instead.
VRBOing a house just south of Lahaina is a great way to stay. There’s something about the view of Lanai and Molokai.
One afternoon my wife contacted George Kahumoku Jr to see if he taught slack key guitar lessons. Not every day you get invited into a Grammy award winning musician’s home. He said she could pay or work on his farm for an hour. She paid..
Should also spend an evening at Java Jazz. Interesting little bar, and the owner can also beat the hell out of a guitar.