What are you into?
The wife and I have been to Hawaii twice and loved both times. It's a bit of a drag getting there (10+ hours in planes and going across 5 times zones) but it's as close to paradise as we've found in the U.S. We left our house in Detroit at 5 AM to make the flight and got to our condo at midnight local time (5 AM Eastern time), making the first day a LONG one. But it's worth it!
We've only spent a little time in O'ahu and that was mostly in Honolulu, which is pretty much any big city anywhere with lots of people and traffic. That wasn't what we were into.
The first time we went, we rented a timeshare condo north of Lahaina for two weeks. That allowed us to eat breakfast and some lunches there and eat dinners out at night. That saved some money but mostly saved time (we HATE spending 3+ hours a day in restaurants). It also allowed us to buy some food at the local farmers market and eat it fresh. The corn on the cob was close to candy, the bananas were amazing and the pineapple is out of this world.
We are very activity-oriented, so we snorkeled every day, did boat trips to see whales (which visit in the winter), bicycled down the volcano, took a helicopter ride and a submarine ride, took in a luau, went bird-watching and shopped. There's a LOT to do in Maui as it is very tourist-oriented. If you plan on snorkeling, think of renting equipment (including dive masks with prescription lenses!) for several days from Maui Dive or other shops. Also, consider going to the aquarium near Maalea to acquaint yourself with the local species before going snorkeling. We like knowing what we're seeing. A lot of people recommend driving the "Hana Highway" from Kahalui (where the airport is) over to Hana. It's actually an exhausting drive with 600+ turns (many with blind corners you have to stop and honk before you go through to keep from hitting oncoming traffic) and 50+ single-lane bridges. Honestly, I'd recommend taking a helicopter ride over and a bus tour back. Leave the driving to someone else. Some folks recommend renting a 4-wheeler and taking the drive south from Wailea-Makena to Hana. That's just plain masochistic in my book. Those roads are (or were) awful.
The second time we went, we spent most of a week in Maui (in Wailea-Makena that time) and did a day-trip to Kauai. We're told that's where the locals go to get away from tourists. The highlight was supposed to be a boat ride up a river to see the "fern grotto" (a fern-covered waterfalls) except that the waterfalls was no more (all diverted to agriculture) and the ferns were long gone. Seeing the "Grand Canyon of the Pacific" was pretty nice though. The island was all very pretty, but we didn't really enjoy it enough for the expense of the flights and all.
We have yet to make it to "the big island" of Hawai'i and would definitely do that in the future. We'd really like to see the island and the active volcano.
In all, our 2-week trip to Maui was the most fun, most relaxing, best vacation we've ever taken. Renting a fully-equipped timeshare condo was great, too. It really felt more like we'd moved there for a couple of weeks than were just visiting and staying in a hotel. I can't recommend Maui enough.
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