We went to Hawaii - the entire family of 10 (three generations) - for two weeks a number of years ago, when our son had just turned 12. He was a very active fellow at that stage in his life. We had a blast. The trip over there was definitely long - we flew to San Francisco and then to Honolulu. From there we were to fly to Maui, but were told our flight had been cancelled months before and the travel agent had failed to fix things properly. So the trip got longer than it was supposed to be. They did get us on another flight, but it was dicey, as it was just before Christmas.
We did tend to wake up early because of the time difference, but our live wire son took it all in stride. One night a few days into the trip we went to a movie about the volcanoes and he fell asleep during the film - was still sound asleep when it was over. :) Other than that he did very well - even after we took a red-eye flight home. It was after we were back home for a few days that all of a sudden he rather hit a wall and needed a solid day of sleep to catch himself up.
But we considered it well worth it to take him. He learned a lot, shared a special time with his grandparents, cousin, aunts and uncles in the process, experienced luaus, got acquainted with another culture or two (there are many Japanese over there too), saw volcanoes, rode in a helicopter, saw whales, snorkeled amongst the beautiful colorful fish, saw black sand beaches, drove the road to Hana, drove up Haleakala in a rainstorm that turned into a flash flood warning situation - it was quite an adventure! But he was a real trooper and had a grand time.
Our trip included 5 days on Maui, which was so beautifully green that I couldn't imagine leaving anything so beautiful. The next five days were on the Big Island. We had a great time there too, though my one comment to you is that there is a greater temperature difference than one may expect on some parts of that island. When we were driving through the ranch and mountainous areas of the island, I was wishing for clothing that was a little warmer than what I had on.
The last three days were on Oahu. We didn't do too many touristy things on that island - no Polynesian Cultural Center... We drove the island, checked out the beaches - and it was winter, so the beaches are more dangerous than they are in the summer. They're not kidding when they tell you it's more hazardous in the winter months - the waters are rougher. But my husband and I traveled there alone a couple of years ago in October and there was no talk about that then.
Prices are high for food, even at the grocery store. We were staying at condo-type hotels, so we had kitchens and could fix ourselves our own breakfasts and lunches. Then we ate dinner out, which Gramma and Grampa paid for.
For my part, I wouldn't hesitate to take them. Travel is great experience and if you've taken them on those other trips and things went well, I think I'd be willing to tackle it if I were in your shoes. Just be sure you take entertainment for the plane (books, little games, puzzles) - and be sure they get up and do a little walking in the aisles, which they did allow us to do. That helped. For us, it also helped that it turned out there was a family right across the aisle from us that had a little boy and since our son loves little kids, that was of interest to him and made the time go faster. Also, on some of the trips we took when he was younger, we kept a diary of the activities of the day. We drew pictures and wrote out the story of what we'd seen and done. They could start writing/drawing about their adventure while yet on the plane. He's a grown man now, but we still have those little notebooks of his trips and they're fun to look at and reminisce over. :)
Hope this helps. Aloha!