Hawaii is actually made up of eight main islands, but most tourist traffic flows to three: Oahu, Maui and the so-called "Big Island" of Hawaii. For first timers, I always recommend a visit to two islands, with one of them definitely being Maui. This is because Maui offers the best combination of resorts, beaches and natural splendor. It also has an airport with flights connecting directly to the mainland, making it an easy entry point.
Maui can actually be looked at as three separate destinations. The island is divided into two large land masses connected by a narrow strip of land known as the "neck". On the northern half, you'll find most of the resorts, restaurants and busy areas, mainly on the west coast. There are plenty of places to stay and eat here, which makes it a popular destination for families. A short drive in the rental car takes you to the north shore where you can watch surfers take on enormous waves. There are also scenic vistas and hiking paths that snake down to the water's edge, although not all are appropriate for very young kids.
The lower half of the island is also home to resorts and multiple condo developments which rent to tourists. There are restaurants here and some shopping, but far less than up north. This is the perfect spot to stay if you and your kids would prefer less crowded roads and more room on the beach. Some of Maui's more exclusive resorts are located here, but we stayed in a luxury condo for six nights for a lot less money, and had unparalleled views of the northern half of Maui above the neck, and the pounding surf below our second-floor balcony. When we wanted to visit the more crowded areas north of the neck, it was an easy 30-minute drive. The lower half of Maui is also home to Mauna Loa volcano which can be reached by car. Bring blankets and plenty of warm clothing if you want to view sunrise or sunset from the peak, as some tourists do. We were fine going in the middle of the day, and most young kids will probably be happier to experience this place that way, too. From the peak, you can stare deep into the enormous caldera, spy the Big Island off in the distance to the south, and marvel at the odd-looking silverthorne plants which only grow near the volcano's summit.
Where's the waterfall?
The third area of Maui worth seeing is on the east side of the island's southern half. Because the Pacific winds usually blow from east to west across Hawaii, the western areas are drier than the east, as the hills and mountains block moisture, and down-sloping winds (which are naturally more arid) rule the climate. In fact, much of the lush vegetation growing in spotty fashion near resorts on the west side has been transplanted there for color and beauty. The opposite is true on the eastern slopes of Hawaii's mountains, and if you want to see the waterfalls and lush tropical jungles that show-up in all those Hawaii travel posters, you have to head east to the "rain forest side". Of all the Hawaiian Islands, Maui is said to offer the best of this sort of environment. It's a quick hop through some pineapple plantations to the head of the "Hanna Highway", a narrow, 15 mph road which snakes along the eastern face of Maui's southern mountainside in a seemingly endless serpentine between exposed rocky cliffs and tropical waterfalls tucked deep into the mountainside. Numerous waterfalls are accessible via short hiking trails. There are also access roads down to the ocean at several points for dramatic ocean side views. Along the main road, some of the locals have fruit stands set-up for refreshment.
You can tour this highway in a day, but the ideal thing to do is to stay in Hanna overnight before making the return trip. The problem is that there are precious few lodging options. Rental houses are plentiful, but be careful. We rented one that was so full of ants and mosquitoes we didn't bother unpacking our bags. We wound-up throwing ourselves at the mercy of the Hanna Maui Hotel, one of most exclusive resorts on Maui, whose staff had one bungalow left and was happy to give it to us for half-price. Needless to say, this was one of the best two nights we've ever spent anywhere---but it was an accident. If you can afford the Hanna Maui, go for it, because it's the kind of place to which movie stars flee when they want to get away (when we were there, Keanu Reeves had been a recent guest). But if you have to rent a house, pay a little more and get a place that will give you some assurance that there are screens on the windows and insulation around the doors to keep the ants out.
One Big Island; two big choices
The two main choices for your second island visit are Oahu and The Big Island. Oahu features the crowded but picturesque Waikiki Beach with its quintessential view of Diamond Head, as well as the historic sites surrounding Pearl Harbor. We skipped this in favor of the Big Island which was not an easy choice for me, since I'm an enormous history buff, and I've heard from people who have been to Pearl that it's a solemn, amazing place to visit. But the lure of seeing an active volcano won out with our kids. Volcano National Park on the Big Island features ribbons of red lava spilling down a rocky mountainside to the sea. The usual plan is to see the park's visitor center during the morning and then head over to the lava flows in the late afternoon so you can see the lava at night when the views are the most spectacular. Of course, there are no guarantees, but depending on when you happen to arrive, you could easily see quite a show. We were eating sandwiches on some rocks when hot red lava gurgled from beneath the surface right beside us! Park Rangers mark a trail each day across the flow (as the safe areas shift regularly). This is great fun for children, but they (and you) do have to be careful, because it's easy to cut your hands and knees on the sharp lava rock if you fall. It's also easy to get severely burned, if you're an idiot and disregard common sense and the Ranger's directions! But my kids absolutely loved this adventure. It was unlike anything else we've ever seen or done together.
Lodging near the volcano park includes small inns and rental homes in and around Volcano Village. We rented a house that included free breakfast at a nearby inn, and this worked well for us. The Big Island also features black sand beaches that are home to enormous sea turtles, a reconstructed ancient Hawaiian village, and a couple of snorkeling spots that are among the best in the entire state.
The ultimate guide
If you go, I would highly recommend picking-up copies of Andrew Doughty's Ultimate Guidebooks for each island you're planning visit. The books have titles like: "Maui Revealed, The Ultimate Guidebook". They're blue with a satellite picture of the pertinent island on the cover. These books break down each hotel, condo, restaurant and beach, telling you updated information about which lodgings and restaurants are most worth the money, the latest prices, and also describing what the surroundings are like. For example, there's one area where the lodgings are cheap, but you may also find thousands of little midges (tiny biting insects) all over the nearby beaches. You'll also learn the different characteristics of Hawaii's many beaches (for example, which are the safest for child swimmers, which are windy vs. calm, and which have the best snorkeling). We found these books invaluable. The writers have actually stayed in all the hotels and visited all the beaches. Maps are included that detail all beach trails. I notice that the series has been recently updated, too.
As for inter-island travel, there are frequent jets the hop from airport to airport, but these have to be budgeted into your expenses. Still, since you've travelled all that way, why not bite the bullet and see more than just one of state's island homes? The planes are like busses with no assigned seating and many locals along for the ride, which is fun.
The road (or flight) less traveled
As for getting to and from Hawaii from Philadelphia, it's a long way and that's probably the biggest reason other than cost that dissuades people from trying it. All I can tell you is that my kids (the youngest was about three at the time) were so into the adventure, they all travelled well. It's a two-flight trip each way. I would recommend changing on the west coast to break things up. You're flying with the sun on the way there, and you're excited, so I'd just try to do it all in one shot, taking care to avoid too long a lay-over in California. On the way back, think about staying in L.A. or San Francisco for a day or two and seeing some sights. This will ease you and your kids back into an east coast time zone. We saved up for this trip for a couple of years so that we could do it right. We were away from home for about 12 days, 6 nights in Maui, 3 on the Big Island and two additional nights in Los Angeles. When we think of the trip now, the travelling is not what comes to mind first. It's the 80-degree water, the eels and giant sea turtles we saw while snorkeling, the incredible sunsets, waterfalls and vistas, and the fun time we shared.
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