My first trip to Hawaiʻi was when I was three years old. After years of returning, I still see travelers make the same mistake. They assume the best trip is the one that squeezes in the most islands.
Our 15-night Hawaii itinerary included six nights on the Big Island followed by nine nights on Oʻahu. We were traveling with our seven-year-old and wanted time to enjoy each place before moving on.
I understand the temptation to add more islands. You have already committed to flying thousands of miles across the Pacific, and every island looks incredible. But seeing more islands does not necessarily mean experiencing more of Hawaiʻi.
Our Hawai’i Itinerary: What Years of Visiting Taught Us
I learned how much one island can offer long before I started planning travel professionally. The first time I took Robert to Oʻahu, we were visiting family on the windward side when rain rolled in. He looked at the gray sky and thought our day was ruined. I told him we would drive across the island.
We crossed through the Koʻolau Mountains and came out to blue skies and warm sunshine on the other side.
That is part of what makes planning Hawaiʻi different. On that visit, a drive across Oʻahu changed our entire day without an interisland flight.
How Much Can Change on One Island
You see that contrast on the Big Island too, only on a much larger scale. Around Kona and the Kohala Coast, black lava rock cuts through the landscape and stretches toward the ocean. As you travel toward Hilo, the scenery becomes greener and wetter.
Near Hawaiʻi Volcanoes National Park, you can walk through lush rainforest before standing at the edge of a volcanic crater.
There is enough to experience on a single Hawaiian island to fill an entire vacation. When we planned this trip, we chose two islands and gave ourselves time to explore both.
Our 15-Night Big Island and Oʻahu Itinerary
We spent August 5 through August 11 on the Big Island, followed by August 11 through August 20 on Oʻahu.
Our stays broke down like this:
- Six nights at Mauna Lani on the Big Island
- Four nights at Turtle Bay on Oʻahu’s North Shore
- Five nights at Aulani in Ko Olina on Oʻahu
That gave us three different home bases while requiring only one interisland flight.
Six Nights on the Big Island
We wanted time for the experiences that brought us to the Big Island, along with afternoons to enjoy Mauna Lani.
That meant spending a day at the beach without feeling guilty that we were wasting it. We could drive to Hawaiʻi Volcanoes National Park without squeezing another excursion into the same day. On another evening, we headed into the ocean after dark to watch manta rays barrel roll inches beneath us.
We still did not make it to a black-sand beach or explore nearly as much of the island as we wanted. But we would not trade our afternoons swimming with green sea turtles and exploring tide pools for another checkmark on the itinerary.
Six nights gave us time to enjoy the resort instead of treating it as an expensive place to store our luggage.
Nine Nights on Oʻahu
On Oʻahu, we divided our time between Turtle Bay on the North Shore and Aulani in Ko Olina. Those stays let us experience different parts of an island I have known since childhood.
We also wanted flexibility to spend time with family and explore beyond the resorts. When a tropical system moved through the islands, that flexibility gave us room to modify our plans.
The North Shore, windward side and leeward side offer different experiences within the same island. Choosing where you stay can matter just as much as choosing which island you visit.
Why We Chose Two Hawaiian Islands Instead of Four
It is easy to look at a map and think a 45-minute flight between islands sounds insignificant. The flight may be short, but changing islands takes more time than that.
You have to pack, return a rental car and get through the airport. Then you collect your luggage, pick up another car and travel to the next resort. Those steps take time you could otherwise spend enjoying your vacation.
One island change felt worthwhile for us. Changing islands every few days would have taken time away from the experiences we wanted most.
Leave Room to Enjoy Where You Are Staying
Some mornings, we wanted to put on swimsuits and decide whether breakfast or the beach came first. We did not want every day to begin with an alarm and a departure time.
Before adding another island, think about what you want your days to include. If that means slow mornings and hours in the ocean, leave space for them alongside your excursions.
We left both islands with things we still wanted to do. Having more time in fewer places was still the right choice for our family.
Planning a Hawaiʻi Vacation Around Our Seven-Year-Old
That breathing room mattered even more because we were traveling with our daughter. We did not want every morning to involve getting dressed before sunrise and hurrying into another rental car.
We wanted her to catch a fish while an eel tried to steal her bait. She had time to search tide pools, learn Hawaiian words at Kids Club and stay in the ocean until she was ready to leave.
Those experiences were just as much a part of the trip as the excursions we booked in advance.
Make Time for the Moments You Cannot Schedule
Some of our daughter’s favorite memories came from watching wildlife and exploring what was right in front of her. We could make room for those moments, but we could not put them on a calendar.
That is where we would encourage a client to begin too. Your family might choose different resorts, excursions or islands. Start with what you want to experience together, then build a trip that gives you time to enjoy it.
There will probably be more you want to see when you leave. After all our visits, we still find ourselves thinking about the next Hawaiʻi trip before the current one ends.
Frequently Asked Questions About Planning a Hawai’i Itinerary With Kids
How Many Days Do You Need in Hawai’i With Kids?
We suggest at least 7–10 days for a Hawaiʻi trip with kids, especially when traveling from the mainland. For more than one island, we suggest additional time, ideally at least 10–12 days. We would avoid squeezing multiple islands into a seven-day trip.
We had 15 nights and chose only the Big Island and Oʻahu. Even then, we left both with things we still wanted to experience. For us, time to enjoy each place mattered more than adding another island.
How Many Hawaiian Islands Should You Visit in One Trip?
There is no perfect number. We would base that decision on your available time and what you want to do. Every island change takes time, even when the flight is short.
For our 15-night Hawai’i itinerary, two islands gave us the balance we wanted. We experienced different parts of Hawaiʻi without heading back to the airport every few days.
Is It Worth Taking Kids to Hawaiʻi?
Absolutely. Our seven-year-old experienced wildlife, Hawaiian culture, national parks and the ocean in ways she could not at home.
The key is leaving room for kids to enjoy those experiences. Some of her favorite memories included exploring tide pools, watching green sea turtles and catching a fish. The eel trying to steal her bait made that last one especially memorable.
What Is the Best Age to Take Kids to Hawaiʻi?
We do not think there is one best age. Plan around your child’s current interests, needs and abilities.
At seven, our daughter could snorkel in the open ocean and complete the Junior Ranger program at Hawaiʻi Volcanoes National Park. She also participated in cultural activities and stayed up for a late-night manta ray snorkel.
A younger child could have a wonderful trip too. We would build a different itinerary around what works for them.
Which Hawaiian Island Is Best for Families?
The best island depends on what your family wants to experience. That is why we would help you choose the island before choosing the resort.
The Big Island gave us volcanoes, manta rays, wildlife and a slower pace. Oʻahu gave us a wider variety of experiences within relatively short driving distances. We loved both for different reasons.
Read our full Big Island vs. Oʻahu comparison for families.
Is Oʻahu or the Big Island Better for Kids?
Neither is universally better. The Big Island was our favorite on this trip because of its slower pace, landscapes and wildlife experiences. Oʻahu offers a wide variety of family activities, beaches, dining and resort options.
We would start with your children’s ages and interests, your travel style and what you picture doing together in Hawaiʻi. Those details help us recommend the island that makes sense for your family.
Big Island vs. Oʻahu for Families
How Far in Advance Should You Plan a Hawaiʻi Family Vacation?
We would start well in advance if you have specific resorts, room categories or experiences in mind. Our Aulani stay reminded us why that matters.
We had kept part of our Oʻahu plans flexible. By the time we arrived at the resort, every reservable restaurant was already booked.
How early to book depends on your dates, island, resort and activities. Booking windows can also change, so we would check current availability for your trip.
Ready to Plan Your Hawai’i Itinerary?
Your Hawai’i itinerary should start with what you want your family to experience. At Taking Vacations, we help you choose islands, resorts and activities that support those plans. We would love to help you decide where to stay, what to book and where to leave room to explore.
START PLANNING YOUR HAWAI’I VACATION
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