Believe it or not I get this question at least twice a month. Here are some nuggets and links that I've gleaned from other posters over the years:
Start with the "101 Things to Do"
website and pick your island(s).
Try posting your questions on Hawaii Threads
. It has a very busy section of people asking about moving to or vacationing in Hawaii, and a lot of the board members live to
know it all
share their experience. You'll get a lot of kama'aina recommendations and posts from the neighbor islands. You might even find rental home bargains that you'd never see on a consolidator's website.
If this is your first Hawaii visit then you should do Waikiki. Very kid-safe beach and plenty of other things to keep everyone entertained. Hanauma Bay, the Diamond Head Lookout hike, & Makapu'u Point whale-watching are right around the corner. There's Sea Life Park, the Polynesian Cultural Center, and plenty of shopping/browsing. Waikiki even has a zoo and an aquarium, which are surprisingly good for their age & location. Kids will forever remember their ride on the Atlantis submarine, although you'll probably forever remember the price.
IMO the best bet for a second island would be the Big Island. Spend some time at the volcano, spend some time at Hilo, spend some time in a cheap rental home in Pahoa, and even drive to the other side for the big city lights of Kailua-Kona. Hilo captures the most of the charm of Old Hawaii while retaining the convenience of Wal-Mart and CostCo. Prices are a bit higher than Oahu but lower than the other islands.
Maui has its own imitation of Waikiki with the Lahaina/Ka'anapali area. We prefer Ma'alaea Bay (lots of rental condos) with the oceanarium, boat harbor, and beaches. Kula is wine country. If the kids are old enough then Oprah's Thompson Ranch land may be open for horseback trail rides. You'll also want to take a snorkel cruise. Don't bother with the road to Hana; your kids will go car crazy and you won't enjoy the driving.
Kauai is our favorite island for Kapaa & Poipu, but there are fewer kid-friendly activities. Lihue is a small airport and the island is more expensive than the Big Island or Maui. Waimea Canyon is breathtaking, as are the eco-tours and the beaches. Our kid was bored.
Molokai & Lanai are very small, very rustic, and (compared to the other islands) very lacking in visitor amenities. Prices are much higher than the other places. We've lived here nearly two decades and I have yet to haul my butt over to either of them, although I'm told that their surfing is like it was in the rest of the world during the 1940s. Some day I will spend a week at Molokai Ranch and another week on Lanai.
Niihau is private property and closed to visitors.
Oahu condo rentals, Oahu vacation rentals Hawaii, CyberRentals
Our best-ever family vacation was on the Big Island's Pahoa coast at a Kapoho Beach rental home
. The gated community had great walking trails, an old lava field to explore, and unbelievable snorkeling. Turtles visited daily. The neighborhood was built with water channels and tidepools to nearly every backyard, so your kids can don their snorkel gear on the lanai and splash among the fish while you man the
frosty beverage & BBQ grill
lifeguard station. The tidepools are very safe (only about 4-6 feet deep) and heated by subterranean lava flows to 85-90 degrees so it's great just to soak (the last eruption there was over 40 years ago). A petrified-forest state park is 15 minutes by car, the volcano is an hour's drive, and Hilo is about 30 minutes. You might need to bring video tapes or DVDs for the evenings after everyone collapses (check your rental house to see if they have a VCR/DVD player... and a TV).
The best flight I've ever had to Hawaii was out of... Newark NJ. Continental goes straight to Honolulu in a 10.5-hour marathon that eliminates a lot of weather & crowds hassles, to say nothing of lost luggage. The longer flights have given our kid a chance to settle in, watch a couple movies, eat a couple meals, and play with all the features of the entertainment system before crashing for a long nap. I never heard a single "I'm bored" and we were much less frazzled when we finally arrived. I think it's way better than switching planes every four-five hours and keeping track of everyone in the departure lounges.
If you're seriously planning to travel during snow season then I'd stay far away from O'Hare. Go through Atlanta or LAX/SFO or even DFW... but not O'Hare.
Get a rental car. You're going to want to shop Ala Moana, snorkel Hanauma Bay, hang the Pali Overlook, drive H-3 both ways, windsurf Kailua, hike Diamond Head, visit the Polynesian Cultural Center, buy tchotchkes at the Aloha Stadium Swap Meet, and cruise the North Shore's surfing contests. Those can all be done via bus or visitor trolley but it's a lot more difficult to make the timing work for you and to haul your loot. Hotel parking isn't too pricey and as long as you avoid rush hours you'll have no trouble getting around. You may even get a weekly rate under $150 with the airfare or the hotel.
Other Hawaii threads:
Waikiki Trip Report/Tips
(added 29 Dec 07)
The Frugal Traveler - Hawaii on a Dime - Travel - New York Times
(added 30 Jan 08)