When most parents think of vacationing with two children under five, their first impulse may not be to choose a destination that requires over 24 hours of flight time. Being the avid adventuring (and maybe slightly crazy) type, that is just what we did in planning our family trip to Hawaii. Now that we’ve done it—and survived—we hope our experience and tips can set the stage for planning your own family adventure to these stunning islands.
How Many Days to Spend in Hawaii
For this trip, we were traveling with other family members, so we began our planning process by deciding the length of time we could visit in consideration of everyone’s vacation leave. We ended up planning eleven days total. To make things easier on the kids (and, therefore, all of us 😊), we chose to break up our flights with stopovers in California on both the outbound and returning journeys.
This step may not be necessary depending on where you are traveling from or if you have older kids or teens who can handle long travel days. However, if you are facing multiple flights to get to the islands and if you have young children, I highly recommend factoring in at least one night at a hotel (both ways) to break up the flying time. Taking an extra day to explore local sights at each stopover is an even better way to spread out the flights while maximizing sightseeing.
With our stops in California in mind, we allotted six days to split between Oahu (O’ahu in Hawaiian) and the big island of Hawaii (Hawai’i). It may not sound like much, but it proved enough to see the sights we had in mind plus a little time on the beach and at the resort pool. If you are the kind of traveler who wants more downtime and less sightseeing, it would certainly be possible to add more relaxation time by eliminating some sights on our itinerary, sticking to just one island, or increasing the length of the trip.
When to Go
To catch the warmest weather with the least rainy days, aim for March-September. To avoid the high season crowds, aim for the shoulder season in April, May, or September. We chose to visit at the end of May around Memorial Day.
TRAIL TIP: If your area of work includes vacation days on national holidays, plan big trips around them to save a day of leave. We often plan big trips around Memorial Day when crowds are still low but weather is nice throughout the US. However, we do tend to avoid flying on the highest travel days, like Memorial Day itself, which are often the most expensive options. Instead, we research flights departing before and arriving after the holiday and choose the more economical alternatives when possible.
What to Do
Itinerary Overview
- Day One—flight to Anaheim, CA
- Day Two–Anaheim, CA
- Day Three—fly to Honolulu and check in at Aulani
- Day Four–North Shore
- Day Five–Honolulu region
- Day Six—Aulani resort day
- Day Seven—fly to Hawaii island; drive to lodging near Hawaii Volcanoes National Park
- Day Eight—Hawaii Volcanoes NP, drive to lodging in Captain Cook
- Day Nine—fly to San Diego, CA
- Day Ten—San Diego, CA
- Day Eleven—outbound flight
Anaheim
For our first stopover in California, we chose Anaheim. Most of us had never been to the Disneyland parks, and this trip seemed a like a good opportunity to visit at least one of them. We thought it would be a fun way to start the trip with the kids, too—albeit an exhausting one, but we figured we would be even more exhausted if we tried to squeeze it into the end of the trip instead. Knowing that the kids would especially be feeling the jet lag coming from the East coast, on our arrival day, we spent a leisurely afternoon at Disney Springs and our hotel pool. Then, we dedicated the next day as our day in Disneyland. Check out our Anaheim post (coming soon!) for more details on our experiences and what we recommend for families with young kids on a first-time visit to Disneyland.
Aulani
Our biggest reason for visiting Oahu was to stay at Aulani, the Disney Resort in Ko Olina. The family we traveled with had been to Aulani before, and they liked it so much, they wanted to return and bring us (well, the grandkids). We are Disney fans, so combining Disney with Hawaii didn’t take any convincing on our part. We’ve included all our favorite parts and suggestions in our in depth Aulani post (coming soon!).
North Shore
We wanted to see as much of the island as we could in a short period of time, and the route between Ko Olina and the North Shore of Oahu offered lots of variety for a day’s excursion: beautiful scenery, beaches and green sea turtle spotting, food trucks, and the Dole pineapple plantation. We’ve chronicled our adventures and tips in our post on the North Shore region.
Honolulu
Visiting the state capital is a must when vacationing in Oahu. The number one priority for our group on this excursion was seeing Pearl Harbor. This destination would have been a trickier one to visit with our young kids if it had not been for our family members. After we finished walking through the museum exhibits, they watched them so that we could take the boat to the memorial site, which requires a long period of respectful silence.
That afternoon, we also checked out the Aloha Stadium Swap Meet and Marketplace, a huge market with all kinds of vendors, surrounding the University of Hawaii’s football stadium. And, when we ran into some trouble in our plan to hike Diamond Head, the dormant volcano just outside of Honolulu, we pivoted our itinerary and found an amazing hike to a waterfall. See our tales and recommendations for all these sights in our Honolulu post.
Hawaii Volcanoes National Park
Part of our reasoning in splitting this trip between two islands came down to the proximity of a national park to our initial destination (Oahu). We didn’t have time to hit both of Hawaii’s NPs, but it seemed a waste to be so close without trying to get to at least one of them. Thus, we wedged in a quick three-day turnaround to see Hawaii Volcanoes NP. It was short, but we still had enough time to leisurely drive the whole length of the park road, stop for a couple of mild-moderate hikes, and eat three meals in the park. Our biggest regret had nothing to do with our condensed timeline, but everything to do with the overall timing of our visit. Read more: here.
San Diego
We knew that at this point in the trip, our kids would be severely jet-lagged and acting unpredictably due to a week bouncing around all the US time zones without any semblance of normal routine. We still wanted to break up the 12 hours of flying with an extended stopover. San Diego felt like a reasonable location for a slower day of sightseeing. Even with a more relaxed pace, we still managed to visit the aquarium, Old Town, the downtown marina, and the La Jolla boardwalk for sea lion and seal viewing—all in one day. Check out the details in our San Diego post (coming soon!).
Where to Stay
Oahu
- Aulani: The family we traveled with are Disney Vacation Club members, and they had saved and borrowed points to make a stay at Aulani possible. We were just the fortunate parents of the grandkids, so we got to tag along. You do not need to be a Disney Vacation Club member to stay at the resort. See our separate post on Aulani (coming soon!) for more information.
Big Island (Hawaii)
- Hawaii Volcanoes NP Region: Our primary destination on the big island was Hawaii Volcanoes National Park. When our initial plan for lodgings didn’t work out, we found an Airbnb a few minutes from the park in Mountain View. I discuss the specifics of where we wanted to stay, what went wrong, and what we would recommend in our Volcanoes NP post.
- Captain Cook: We needed another place to stay close to Kona before our flight to California. Most of the hotel options we found in Kona were pricier than we were hoping to pay for a single night, so we broadened the radius of our search and chose a hotel in Captain Cook, about 40 minutes south of the Kona International Airport. For more details on the planning process and our stay there, see our post on the Volcanoes NP and the section on where to stay.
TRAIL TIP: If you are trying to save money when vacationing with your kids, be willing to make at least some sacrifices on accommodations. This is easy to do if you have any destinations where you will only be staying for one or two nights. Aim to find lower cost options for those shorter stays. Yes, we like swanky hotels and resorts, too, but we also like to save money, especially when we truly only need beds and a bathroom for a brief stay. Mixing a few economical choices with a more high-end option here and there can give you the best of both worlds if you want to save a little without completely sacrificing quality at every stay.
Is a family vacation to Hawaii worth it?
Even if traveling to Hawaii will cost you 24 hours of flying time, it will be worth it. Whether you are adventure seekers, beach lovers, history aficionados, foodies, or National Park explorers, the islands of Oahu and Hawaii offer plenty of opportunities for everyone to explore, relax, learn, and recharge as a family.
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